The Upside

Top 3 Mistakes to Avoid as a Consultant or Freelancer - The Upside

Building a successful independent consultancy requires moving past the initial chaotic phase by adopting specific strategic behaviors. While the industry lacks a single set of universal best practices, certain patterns lead to burnout or failure. One major error is maintaining an overly broad offering. Many consultants fear that narrowing their focus will limit opportunities, but a specific niche actually makes a business more memorable and valuable. A well defined niche should focus on a specific industry, function, and clear results like revenue growth or cost savings. For example, shifting from general strategy to building analytics for capital raises makes the pitch much stickier for prospects. Pricing is another area where new consultants often stumble. Many attempt to win business by offering lower introductory rates or undercharging to gain experience. This strategy backfires because it undermines the consultant's perceived value and signals a lack of confidence. If you do not have confidence in your own abilities, a client certainly will not either. Instead of a one size fits all approach, consultants should consider flexible pricing structures like internal tiers, monthly retainers, or value based pricing that reflect their years of professional experience. Starting with a number that represents true value prevents the struggle of trying to raise rates with the same clients later. Finally, the approach to business development often focuses on the wrong targets. Creating cold outreach lists of unknown companies is generally the least effective way to start. Successful consultants prioritize their existing network through a three tier strategy. This includes former supervisors, past colleagues, and broader professional or alumni connections. Reconnecting with these warm contacts through personal meetings is the fastest path to securing lucrative contracts. Showing up in person and making it easy for people to say yes helps you stand out from the crowd. Success in the six figure range depends on the ability to clearly communicate how your services solve specific pain points or drive business growth.

If You Do Nothing Else in Business, Do This - The Upside

Business success is frequently quantified by profit margins and growth, but the most enduring part of a professional career is the legacy of how you treat people. This principle is grounded in a personal story from mid-2000s New York City involving a doorman at a popular nightclub who was also a partner in the business. Despite the author being a frequent guest and knowing the doorman by name, he chose to treat her as if she were invisible when she arrived alone one night. This lack of basic human recognition left a lasting negative impression that persisted for over fifteen years. The core lesson is that people will always remember how you made them feel, regardless of what was said or the specific business transaction. In the context of building a consultancy or a brand, every interaction contributes to a long-term reputation. While the nightclub was financially successful, the partner's choice to use his platform to ignore or exclude people created a legacy of negativity. This highlights a critical distinction between being successful and being respected. For independent consultants and business owners, the choice of how to wield power and influence is critical. Even when a specific request cannot be met, such as admitting everyone to a crowded venue, there is a choice in how that message is delivered. Choosing to lift others up rather than using a position to diminish them is the foundation of a meaningful business. Erin Halper, the founder of The Upside, uses this experience to frame her approach to the future of work. Her organization focuses on helping professionals transition from corporate roles into independent consulting, emphasizing flexibility, autonomy, and purpose. The ultimate goal is to ensure that a business helps and lifts others rather than just focusing on scale. This philosophy suggests that if you do nothing else in business, you should treat people in a way that you want them to remember forever.

24 Entrepreneurs on Why They Left Corporate Jobs to Found Companies - Business Insider

Success is being redefined by women who trade corporate ladders for personal fulfillment and direct problem solving. These 24 founders left roles at major firms like McKinsey and Bain to build companies that address gaps they experienced firsthand. Common drivers for leaving included a lack of representation for women of color, toxic law firm cultures, and the rigid structures of corporate fashion and healthcare. Many transitioned into strategic consulting or service based businesses to gain flexibility and control over their schedules. Several founders focused on health equity and specialized services. Ivelyse Andino started Radical Health to improve healthcare in marginalized communities, while Jamie Lieberman created a virtual law firm to escape traditional legal industry stress. Others, like Tara Zedayko, applied corporate expertise in human healthcare to the pet industry. The recurring theme is a shift from being a small part of a large machine to having a direct, measurable impact through independent ventures. The transition often involves leveraging deep domain expertise. For example, Rocio Brusseau used 20 years of brand strategy experience to launch a growth focused agency, and Erin Halper founded The Upside to help other women build successful consultancies. These stories highlight that entrepreneurship isn't just about new products; it's often about redesigning how work fits into a meaningful life. The move toward independent work is frequently sparked by a desire for 'ikigai' or a reason for being that aligns personal values with professional superpowers.

24 Good Reasons to Quit Your Corporate Job and Strike Out On Your Own - The Upside

Transitioning from a corporate 9-5 to independent work often stems from a desire for greater autonomy and the need to solve specific problems that corporate structures restrict. Many professionals find themselves constrained by rigid job descriptions that stifle curiosity and risk-taking. This shift is frequently driven by a misalignment of values or a realization that a once-coveted dream job has become a soul-eating routine. Flexibility is a major catalyst, especially for those with children or those facing life changes that require more control over their schedules. Beyond personal freedom, the move to strike out on one's own is often fueled by a mission to fill market gaps, disrupt specific sectors, or empower others. The goal is to build a career that offers both financial stability and the freedom to travel or work on one's own terms. Ultimately, the transition is about tapping into full potential and redefining success outside traditional employment frameworks.

2020 Was My Company’s Biggest Year Yet. Here’s How We Did It. - The Upside

The Upside, a community for independent consultants, achieved significant growth in 2020 by quadrupling its revenue despite the global economic downturn. This success stemmed from a combination of strategic positioning and a digital first business model that was already in place before the pandemic. By focusing on a specific niche of industry experts rather than offering a generalist entrepreneurship platform, the company provided tailored value that resonated with professionals looking for specialized support. The founder notes that while many competitors offered broad women's entrepreneurship courses, The Upside's specific focus on consultants allowed them to capture a market that was tired of one size fits all solutions. The launch of The Upside Accelerator was planned months in advance, which meant it was ready exactly when corporate professionals began leaving their jobs to seek autonomy. Because the company was built as a virtual community from the start, it avoided the operational friction that traditional event based organizations faced when trying to pivot online. This digital native status shifted from a point of criticism to a major competitive advantage, leading to oversubscribed membership and waitlists. The market perception of digital only communities changed overnight, moving from a secondary option to a premium standard. The company also maintained a bootstrapped approach, avoiding venture funding to focus on sustainable, high quality growth. This allowed for a more curated and intimate environment compared to high volume, low cost competitors that struggled to retain members during the chaos. As revenue increased, the founder reinvested in a core team, shifting her role from working in the business to working on the business. This transition enabled the exploration of new opportunities and further solidified the company's position as a leader in the fractional and independent consulting space. The narrative emphasizes that staying resilient and maintaining a clear mission leads to financial success without compromising core values or answering to outside investors.

You Could Be In An Abusive Relationship With Your Corporate Career. Here’s Why. - The Upside

Corporate environments often mirror emotionally abusive relationships through specific manipulative tactics designed to keep employees feeling small and dependent. These behaviors manifest during performance reviews where managers focus on flaws to justify lower pay, or when leadership uses economic uncertainty to foster a sense of fear. Companies frequently leverage the narrative that there is a line of people waiting to take your job, which serves to suppress salary demands and prevent talent from exploring better opportunities. A common experience involves supervisors making verbal promises that are later rescinded by upper management under the guise that the job itself is a form of paid education. This culture aims to keep professionals feeling undervalued and grateful for minimal tokens of appreciation, such as small bonuses that do not reflect actual performance or goals surpassed. The reality is that replacing high performing talent is costly and difficult, yet corporations benefit from maintaining the illusion that employees are easily replaceable. This dynamic is particularly damaging for professionals over 50, who may face ageist assumptions about their technical skills despite decades of deep expertise and relationship capital. Transitioning into independent consulting or advisory roles offers a path out of this cycle. In the independent market, longevity and specialized knowledge are treated as premium assets rather than liabilities. By recognizing their true market value and moving away from traditional employment structures, professionals can reclaim autonomy and achieve better financial outcomes through their own consultancy or advisory practice.

You're Not a Business Owner Unless You Do This - The Upside

Platforms like Instagram, Uber, and Upwork offer convenience by aggregating customers, but they ultimately own the relationship. If a business relies 100% on these third parties for growth, it isn't building any intrinsic value. The success of these platforms actually depends on the user's inability to find customers independently. For instance, a driver who can manage their own booking and payment wouldn't need to pay Uber a 25% commission. Similarly, freelancers who can't find their own clients are beholden to Upwork's 10 to 20% fees. This dependency creates significant risk. If Amazon raises seller fees or a social media platform changes its algorithm or bans an account, the business's profitability and communication channels vanish instantly. True business ownership requires mastering the skills to find and keep customers directly. There is a growing trend toward digital courses and learning programs that teach these essential skills. Experts now offer training on building email lists, managing e-commerce sites, and mastering organic or paid traffic. These tools allow solopreneurs to own their audience and build a business that can't be taken away. The Upside shifted its model from a client-matching platform to an accelerator because matching didn't help consultants become actual business owners. To be truly viable and profitable, a consultant must move beyond being talent for a platform and become a self-sufficient entity.

Are Paid Professional Membership Communities Worth It?

Many professionals struggle to justify the cost of paid networking groups because they focus on immediate transactional returns like referrals or press mentions. The real value of these communities is found in the long-term impact of specific connections. For example, a single relationship with an advisor like Belma McCaffrey can be the difference between folding a business and scaling it. In one instance, a conversation about business models during a period of burnout led to a complete pivot that saved the company. Three years later, that same business is thriving because of a single connection made through a community called Dreamers and Doers. Beyond emotional support, these networks provide access to insider data that isn't publicly available. Ezinne Okoro, a DEI leader at H&M, provided specific speaking and workshop fee benchmarks that allowed other members of The Upside to double or even triple their rates. This type of information creates a direct financial ROI that far outweighs membership dues. It demonstrates how a single conversation can fundamentally change the revenue trajectory of a consulting practice. The impact also extends to personal growth and brand advocacy. Members like Sue Groner not only provided parenting advice and emotional support during the pandemic but also became active promoters of the community, driving new memberships through word-of-mouth. Similarly, meeting authors like Kara Richardson Whitely can lead to significant perspective shifts that improve a consultant's empathy and worldview. These interactions often happen in smaller, niche groups like The Cru or The Co-Co. To accurately evaluate a membership, you should list every person met through the organization and identify the specific personal, professional, or emotional impact they had. This includes finding close advisors, gaining invaluable advice that led to better decisions, or being introduced to resources that changed your life. If a community provides even one of these priceless connections, the investment is usually justified. The true measure of ROI is the cumulative value of these relationships over time.

The Definitive Guide on Starting a Consulting Business - The Upside

Launching a successful consultancy requires a shift from a job-seeker mindset to a business-owner perspective. The process begins with deep market research by interviewing 10 to 15 people within an existing network to identify specific pain points and goals. These conversations reveal patterns that define a niche and provide the exact language potential clients use to describe their problems. Using this mirrored language on social profiles and in pitches builds immediate credibility. Services should be packaged around four pillars of value: growing revenue, saving money, providing unique access, or solving a major operational headache. Every consultant needs a pitch of 10 words or less that clearly states what they do and for whom, avoiding unnecessary adjectives to ensure the message is memorable and referable. LinkedIn serves as the primary credibility hub, often removing the need for a dedicated website in the early stages. Profiles must be optimized with results-oriented language like boosted or built rather than passive terms like managed or assisted. Content strategy should focus on weekly posts that demonstrate subject matter expertise through industry commentary or trend analysis. When it comes to business development, cold outreach is secondary to exhausting an existing network through friendly catch-ups that plant seeds for future work. Pricing is a critical hurdle where new consultants often fail by undercharging. Starting with low rates attracts low-quality clients and makes it difficult to raise prices later. Instead, consultants should set high-ticket minimums and be willing to walk away from misaligned opportunities. The sales process itself is a mutual discovery of fit rather than an interview. By asking targeted questions about a prospect's goals and the cost of inaction, a consultant positions themselves as a closer who solves high-value problems for a select group of quality clients.

Here Are 3 Magic Questions That Will Help You Close More Clients, Instantly - The Upside

Closing consulting clients requires a fundamental shift in how you handle initial meetings. Instead of viewing the session as a job interview or a sales pitch, you should treat it as a prospecting conversation to determine mutual fit. Many consultants fail because they let the client lead the discussion, which positions the consultant as a subordinate rather than an expert. By taking control and driving the boat through strategic questioning, you demonstrate the confidence and prestige necessary for high-level advisory work. The process starts by asking why the client agreed to meet in the first place. This open-ended approach lets the client describe their problems in their own words. It is essential to listen for the specific language they use so you can mirror it back to them. This initial question is just the start of peeling back the layers of the onion to find the true end goals behind their surface-level requests. Once the pain points are clear, the conversation must pivot to value. Asking what the client stands to gain by reaching their goals or what they stand to lose if the problem persists forces them to quantify the situation. Whether they are looking to save millions or grow revenue by a specific margin, getting a dollar amount on the table early helps shift the focus from your cost to their potential ROI. This makes value-based pricing much more natural later in the process. Finally, establishing a timeline is critical for managing your pipeline and avoiding being ghosted. Asking how soon they need to start reveals their level of urgency. If the timeline is vague, asking why the issue isn't an immediate priority provides even more context on their internal situation. This structured approach ensures you spend your time on high-intent leads while maintaining a professional, authoritative stance throughout the sales cycle.

Do this to attract consistent consulting clients

Building a sustainable consulting business requires a solid foundation, much like constructing a house from the ground up. Many consultants struggle to find clients because they skip the groundwork in favor of quick fixes or inconsistent efforts. Erin Halper, the founder of The Upside, argues that the most effective foundation for any service-based business consists of two specific, non-negotiable actions: optimizing your personal LinkedIn profile and posting consistent content for a minimum of six months. The article points out that when consultants ask how to get more clients, the answer almost always comes back to these two pillars. Most professionals fail to attract consistent work because they haven't committed to the long-term discipline of content creation. By focusing on these areas, you position yourself as a visible expert in your field. This visibility ensures you stay top-of-mind for your existing network and potential leads. Over time, this creates a warm pipeline where clients come to you, significantly reducing the need for manual business development, cold outreach, or aggressive sales tactics. Halper shares a specific success story involving Upside member Stephanie Blair Caranante. After posting about two recent podcast appearances, Stephanie saw a 75% increase in LinkedIn profile traffic and a 50% increase in website traffic. This demonstrates how external authority, like podcasts, can be funneled through an optimized LinkedIn presence to drive measurable interest. The core philosophy is that content acts as a silent salesperson. If a reader finishes an article, the content has already proven its value and the author's expertise. For independent consultants and fractional executives, this inbound motion is the key to achieving the flexibility and autonomy they sought when leaving corporate life.

The Magic Formula for Consultants to Increase Opportunities

Consulting success relies on a specific balance between technical ability and self-valuation. While high-level skills are necessary to provide ROI and generate referrals, they are not enough to sustain a healthy business on their own. The missing piece for many is knowing your worth, which involves understanding the high value provided to clients. Without this, consultants often leave money on the table and fall into a cycle of feast or famine. Combining these two elements creates a business that generates consistent opportunities and provides the freedom to work whenever and wherever you choose. This approach is also the best way to avoid a scarcity mindset, which often causes consultancy businesses to fail. When evaluating potential deals, applying this formula helps ensure you are not just executing work but are being compensated for the actual impact you have. Erin Halper, founder of The Upside, emphasizes that recognizing your own value is the catalyst for attracting better opportunities and maintaining a renewed sense of purpose in a corporate-to-consulting transition. She also reminds consultants to always account for their own costs and taxes when structuring these deals.

6 Organizational Culture Experts Weigh in on The Great Resignation and What it Means for the Future of Work - Thrive Global

The Great Resignation represents a massive shift in the labor market where one in four workers plan to leave their roles to prioritize mental health and well-being. This movement is driven by a fundamental change in how people value their time and the quality of their workplace culture. Experts like Emily R. Williams of Forward Ever Global point out that remote work gave employees, particularly women of color, the psychological safety to recognize toxic environments and demand more equitable treatment. This shift forces a new level of accountability on employers who previously prioritized output above all else. Corporate culture is moving away from the grind mentality of previous decades toward a human-centric model. Michal Levison from Seasoned Moments advocates for using positive psychology to treat employees as individuals rather than cogs in a machine. This approach is linked to better creative solutions and higher retention. Similarly, Stephanie Loewenstern of Bright Link Talent observes that workers feel more empowered to seek joy or even start their own businesses, moving away from traditional corporate structures. Flexibility and remote work have transitioned from optional benefits to essential requirements for top-tier talent. Jennifer Rutha notes that high-performing individuals are now refusing to compromise on their schedules, forcing companies to permanently adopt distributed work models. Stephanie De Flora highlights a significant disconnect between individual motivations and the rigid mandates of shareholders, suggesting that organizations must bridge this gap at a personal level to survive. The future of work is tied to holistic wellness and inclusivity. Kasia Smith of Copilot Wellness argues that as technology makes long-term distributed work viable across more industries, employees will naturally gravitate toward roles that invest in strategic wellness support. Organizations that fail to adapt to these new expectations regarding flexibility and human sustainability will likely face a continuous cycle of resignations and eventual failure.

​​5 Steps Every New Consultancy Startup Needs To Make it Past Year 1

The pandemic triggered a significant shift in the workforce, with many professionals moving into consulting to leverage their skills independently. This transition led to a 24 percent increase in new business applications in 2020. However, launching a consultancy requires more than just expertise; it demands a shift from an employee mindset to an entrepreneurial one. To survive the first year, founders must master five specific areas. First, financial literacy is non-negotiable. Dorothy Kolb, CEO of dk east associates, notes that founders often avoid their financial statements because the early numbers can be intimidating. Failing to understand these metrics makes it impossible to course-correct when things go wrong, leading to irreversible damage. Second, managing decision fatigue is critical. Sonia Narvaez, founder of Operation QOL, explains that wearing too many hats causes internal chaos and paralysis. Establishing a daily structure and focusing on non-negotiables helps maintain momentum and prevents getting lost in non-essential details. Third, successful consultants actively seek out feedback. Dayna Lapkovsky of frank Women's Leadership emphasizes that inviting feedback allows a business to flourish by identifying roadblocks and providing strategic opportunities to adapt. This requires a flexible workstyle and the avoidance of rigidity. Fourth, defining a specific niche is essential for clear communication. Maggie Phrompechrut of Centerstone Consulting argues that a well-defined specialty helps set client expectations and proves the consultant's specific value add. This niche forms the foundation of the business. Finally, consultants must play the long game. Evan Sargent of Commit points out that it can take three years for relationship building to yield consistent results. Developing a memorable, sticky brand from day one ensures that when a potential client is finally ready to hire, they remember who to call, even if years have passed since the initial contact.

5 Resolutions To Supercharge Your Business In 2022

Business owners and consultants often struggle to identify which New Year's resolutions actually drive growth versus those that just add noise. Erin Halper, CEO of The Upside, highlights five specific strategies from successful entrepreneurs designed to optimize operations and scale impact. The first strategy focuses on proactive networking. Eliza Erskine of Green Buoy Consulting suggests that consultants should aim to connect at least two people in their network every month. This "low-touch, high-reward" habit builds significant trust and keeps the consultant top of mind without requiring a hard sell. It transforms networking from a passive activity into a strategic service that solves problems for others. Strategic journaling is the second pillar. Alison Coward of Bracket Creative recommends a weekly reflection process centered on five questions: what happened, what was done, what was learned, how the founder feels, and what they are thinking about. This practice provides clarity on strategic direction and acts as an energy audit. It helps founders distinguish between work that fuels them and tasks that drain them, making it easier to decide what to delegate. Third, investing in a mentor provides an essential outside perspective. Mina Black emphasizes that mentors help identify blind spots and strengths that founders often overlook while caught in daily operations. This external guidance is often the most significant factor in a business's evolution. Fourth, streamlining operations through goal definition is crucial for scaling. Sheela Gonsalves notes that taking an inventory of responsibilities allows owners to see where they are wasting time on low-value tasks. Hiring a virtual assistant is presented as a way to "think big" by freeing up resources for marketing and business development. Finally, rethinking the weekly schedule can revolutionize productivity. Rosie Kosinski suggests front-loading meetings on Mondays and Tuesdays. As the week progresses, meetings taper off to make room for deep creative work and deliverables. This approach creates predictable deadlines and provides the breathing room necessary for high-level brain function and morale.

Are You Good at Saying No? - The Upside

Saying no is a critical skill for maintaining business focus and personal energy. Many professionals struggle with this because they want to explore every opportunity, attend every event, and meet everyone who reaches out. However, a pattern of saying yes too frequently eventually tests your capacity and dilutes your impact. The core strategy for 2022 and beyond is to commit to saying no to anything that is not 100% aligned with very specific business goals and intentions. This level of discipline means accepting certain trade-offs, such as missing out on potential opportunities, meeting fewer people, or even unintentionally offending someone. The benefit is the ability to fully serve the members and community who gain the most value from your work. To implement this effectively, use specific tactics to manage expectations. Create an email auto-reply that clearly explains your current focus and goals so people understand why you are being selective. For meeting requests that fall outside your primary focus but are still difficult to decline, use a calendar booking link that only offers one opening per week. This creates a natural bottleneck that protects your time. Additionally, establish firm boundaries for how many events you will attend each month and maintain those limits strictly. By focusing your time and energy on building value and removing distractions, you can maximize the impact you want to make in your professional field. Erin Halper, the founder and CEO of The Upside, emphasizes these boundaries as a leading authority on independent consulting. Since 2017, she has helped thousands of professionals move from corporate roles into consulting to find more flexibility and autonomy. Her approach suggests that the future of work requires a renewed sense of purpose, which is only achievable when you stop letting external requests dictate your schedule. By saying no to the noise, you are effectively saying yes to the work that matters most to your business and your clients.

The Hourly Rate Trap - The Upside

Transitioning from agency subcontracting to direct client relationships is the primary lever for scaling a consulting business from a standard freelance income to seven figures. Many high-level professionals with decades of experience fall into the trap of working under agencies as a path of least resistance. While this provides steady work, it creates a hard ceiling on earnings because agencies typically pay hourly rates to stay within their own project budgets. In this model, the agency owns the client relationship, which prevents the consultant from building the long-term equity and referral networks necessary for a sustainable practice. The case of a brand strategist with 25 years of experience illustrates this shift. Despite her deep expertise, she was initially charging a flat $175 per hour as a subcontractor. By moving away from agency work and engaging clients directly, she was able to implement value-based pricing. This approach decouples income from time, allowing a consultant to be rewarded for their efficiency and the specific outcomes they deliver rather than the hours they log. When you charge for the project value, you earn a higher profit margin by being smart and fast with deliverables. Making this pivot requires a significant investment in business infrastructure. Consultants must level up their client generation strategies, refine their messaging, and learn to communicate their worth directly to decision-makers. The strategist in this example reached a projected $800,000 in annual revenue within 18 months of turning down agency work. The core takeaway is that depending on another company for your pipeline is a disservice to your earning potential. True growth in the independent consulting market comes from mastering the ability to bring in clients, close contracts, and charge based on the full impact of your work.

Why transparency is a competitive advantage - The Upside

Pricing transparency serves as a powerful tool for independent consultants to benchmark their value and escape the trap of undercharging. Within professional communities like The Upside, sharing specific project scopes and fees can fundamentally shift a consultant's financial trajectory. A notable example involved a consultant proposing a $25,000 fee for a half-day workshop with a large corporation. This disclosure triggered a broader discussion where peers shared their own benchmarks, ranging from a $6,500 day rate to suggestions that $50,000 was more appropriate given the client's scale and the executive level of the participants. This collective sharing reveals significant disparities in how consultants value their time and expertise. While some were charging between $10,000 and $20,000 for full-day sessions, others realized they needed to quadruple their rates to align with market standards for high-impact corporate work. A critical factor often overlooked in lower quotes is the extensive labor required to create the programming before the actual event. Transparency ensures that these hidden costs are factored into the final price. By being vulnerable about their rates, consultants can identify opportunities to close the rate gap and achieve greater economic equality. This practice moves the industry away from isolated guessing and toward a data-driven approach to monetization. For fractional leaders and advisors, engaging in a trusted network to exchange pricing data acts as a competitive edge, allowing them to negotiate from a position of knowledge rather than uncertainty. Ultimately, this openness pushes individuals to think bigger and demand compensation that reflects the true value of their impact on large organizations.

What I learned in 5 years of running The Upside - The Upside

How to Decide Whose Advice You Seek - The Upside

Independent consultants often face feedback drift where clients stall projects after seeking opinions from unqualified friends or colleagues. This specific case involves a branding consultant whose client repeatedly changed their mind, causing significant stress and project delays. The solution lies in being highly selective about whose feedback is invited. A useful analogy compares asking a grandmother for marathon advice versus asking a running coach. While a grandmother might focus on the dangers and suggest stopping, a coach provides a structured plan to reach the finish line. Professional success depends on surrounding yourself with people who want to see you advance and who share your specific goals and values. It is critical to seek advice from experts with deep topic knowledge rather than generalists or social connections. Ultimately, the advice emphasizes trusting your own decision-making while filtering for high-quality, expert-led input.

Experimenting on difficult clients - The Upside

Identifying a potentially difficult client early is a valuable skill for independent consultants. When a lead seems like they might be a headache or not worth the standard rate, it creates a unique opportunity to experiment because there is nothing to lose. Instead of simply walking away, consultants can use these situations to test the limits of their pricing and contract terms. Specific tactics include doubling or tripling standard fees, requiring full payment upfront, and setting aggressive deadlines for contract signatures. This approach removes the fear of rejection since the consultant was already prepared to decline the work. Members of The Upside community have found that these difficult clients often agree to the higher rates and stricter terms immediately. This outcome provides a significant psychological shift for the consultant. It proves that their market value is likely higher than they realized. These experiments serve as a catalyst to raise rates for all future clients, not just the challenging ones. The strategy turns a negative lead into a data point for business growth and increased profitability.

5 Cash Flow Strategies Every Startup Needs to Implement Now | Nasdaq

Cash flow serves as the primary indicator of a business's health, especially for startups navigating shifting economic environments. While profit measures long term survival, cash flow sustains daily operations. One effective tactic involves stashing a percentage of revenue into separate accounts for taxes, profits, and direct costs. This "out of sight, out of mind" approach prevents founders from being caught off guard during tax season and provides a reserve for unexpected crises. It ensures that the operating account only reflects what is truly available for monthly expenses. Measuring lead conversion is equally critical. Instead of simply seeking more leads, founders should focus on maximizing the ones they already have by understanding every step of the customer journey. Building this "measuring muscle" helps identify specific friction points in the sales process and prevents the common mistake of overspending on top of funnel growth without a conversion plan. Similarly, assessing cash runway provides a clear view of when capital will be exhausted based on current burn rates. For technology startups, maintaining an 18 month runway is a standard benchmark. This timeline allows 12 months to gain traction with investors and another 6 months to close the next funding round. Improving cash flow also requires shifting spending focus from lead generation to actual sales. Making an offer at the point of highest excitement, right when a lead is generated, can drive down Customer Acquisition Cost (CAC). Even a nominal sale at this stage helps validate paid media efforts and increases the likelihood of future upsells. Finally, treating bankers as strategic partners rather than just service providers can unlock better credit terms and networking opportunities. Bankers often have insights into traditional credit markets and can help troubleshoot operational issues more effectively than standard customer service channels. Establishing these relationships early allows for smoother navigation of changing financial needs.

The 3 C's of Great Client Relationships - The Upside

Erin Halper, founder of The Upside, outlines a framework for maintaining strong client relationships based on three pillars: Communication, Commitment, and Compromise. This approach, originally shared as marriage advice, serves as a diagnostic tool for independent consultants to evaluate the health of their professional engagements. Communication requires establishing consistent feedback loops and being direct about what is needed to succeed. It also involves clearly articulating value and asking for appropriate compensation. Commitment is a two-way street where the client commits to timely payments and the consultant commits to achieving specific goals, with both parties prioritizing each other's best interests. Compromise involves flexibility, such as meeting in the middle on contract terms to close a deal or adapting to a client's evolving needs. When a relationship feels strained, these three categories help identify the specific weakest link that needs attention.

Recognizing Red Flags and Ending Client Relationships

Identifying the right time to move on from a client is a critical skill for independent consultants. The primary challenge is often the delay between recognizing a problem and taking action, which wastes valuable time that could be spent on more productive business activities. Key red flags include clients who ignore professional advice, constantly shift the definition of success, or exhibit disrespectful behavior such as belittling or interrupting. Other warning signs involve non-responsiveness or pushback regarding rate increases and a general lack of respect for the consultant's time. To address these issues or exit the relationship while maintaining a positive reputation, consultants should prioritize direct, heart-to-heart conversations. A specific strategy involves requesting a course correct call to review the original scope, initial discussions, and current challenges. Being honest about the roadblocks preventing the client from reaching their goals is essential. Ultimately, the flexibility to walk away from misaligned work is a core benefit of self-employment. Creating space by removing bad clients allows for better opportunities to fill the vacuum.

Inside a Premium Community Business — Friendly Nooks

The Upside is a high-end community for independent consultants charging $189 per month, totaling over $2,000 annually. Despite this premium price point, the group maintains low cancellation rates and high engagement levels. A key milestone was the migration from Facebook to Circle. While many founders fear losing engagement during platform shifts, The Upside saw an increase in posts and connections because the value proposition was already clear. The community's stickiness comes from targeting members on nearly identical growth journeys, specifically those scaling consulting practices to serve larger clients. Because members share similar business models but different subject matter expertise, they naturally collaborate and refer work to one another. The organizational structure relies on three levels: the large group, small groups like industry pods and masterminds, and curated 1:1 connections. Founder Erin Halper still hand-picks these 1:1 introductions, providing a human touch that automated systems often lack. Leadership is decentralized by assigning members to lead pods and facilitate open house events for prospects. This model suggests that higher pricing actually solves common community issues like low engagement and founder burnout by attracting committed members and allowing the group to remain small enough for meaningful relationships.

Value-based Pricing: Pricing Your Services Based on Results

Value-based pricing shifts the focus from benchmarking against market rates to pricing based on the specific impact a consultant has on a client's bottom line. Credentials like books, degrees, or corporate experience only matter in the context of the value they generate. Every client engagement fundamentally seeks one of four outcomes, known as the Four Pillars of Value: growing revenue, cutting costs, gaining access to specific resources or networks, and solving headaches that prevent growth. To implement this pricing model, consultants must use the prospecting phase to uncover these motivations. This involves asking targeted questions to understand what success looks like, what is preventing the client from solving the problem internally, and the potential financial gain or loss associated with the project. By quantifying the cost of inaction or the value of a successful outcome, consultants can move away from hourly billing and set rates that reflect the total impact of their work. Ultimately, there are no fixed market rates for professional services, only the value a client is willing to invest to achieve their desired results.

5 Communication Tips to Minimize Client Ghosting - The Upside

Client ghosting often happens in what sales expert Allison Davis calls the Bermuda Triangle. This is the period after a proposal is sent when a prospect stops responding to follow-up emails. To avoid this, consultants should refine their sales process and mindset. One critical mistake is sharing high-value ideas during the prospecting stage. Giving away solutions for free before a contract is signed reduces the incentive for a client to close the deal. Solutions should be reserved for the engagement itself. Pricing should never be a surprise in a written document. Discussing a price range verbally during the first conversation ensures alignment before any formal work begins. For example, stating a project will likely land between $50,000 and $65,000 allows the consultant to gauge the prospect's reaction immediately. The formal proposal then serves only as a confirmation of what was already discussed rather than a place for new information or unexpected costs. If more clarity is needed, a second discovery meeting is better than a complex, unexpected proposal. Adding a "good until" date to proposals creates natural urgency and provides a professional reason for follow-up. This also protects the consultant from the PITA tax where a client returns much later expecting outdated rates. Reviewing the proposal live during a meeting instead of emailing it is another effective tactic. This allows the consultant to address objections in real time and read the room. Ultimately, preventing ghosting requires a mindset shift. The consultant must lead the conversation and recognize that their time is a scarce resource. Being willing to walk away from misaligned opportunities is just as important as closing them.

Unlocking Your Special Sauce: How to Stand out and Close High-value Clients - The Upside

Standing out in a crowded consulting market requires identifying a "Special Sauce," which is the unique combination of experience and traits that justifies premium rates. This differentiator isn't just a task or a personality trait. It is tangible evidence that a consultant can replicate past successes for new clients. The framework breaks this down into four distinct categories. Pedigree involves leveraging high-profile education or past employment at major firms to build immediate trust. For example, mentioning a background at Stanford or Google immediately signals a certain level of competence to a prospect. Results focus on "hero" case studies, such as raising significant capital or achieving specific, massive growth metrics that blow people away. This provides the measurable proof that clients need to feel comfortable with high fees. Specialized Skill or Access highlights the value of scarce technical abilities or deep industry networks that clients cannot easily find elsewhere, such as knowing all the key players in a specific retail arena. Finally, a Unique Story uses a consultant's personal background, like military service, to create a memorable and intriguing brand that makes people want to know more. By placing these elements at the forefront of LinkedIn profiles, websites, and sales conversations, consultants can move away from being viewed as a commodity and instead position themselves as high-value partners. Clients are essentially buying measurable experience in hopes that the consultant will replicate that success for their specific goals. Owning this unique value proposition is essential for closing larger contracts and achieving the flexibility and autonomy associated with successful independent consulting.

Escaping the Hamster Wheel: Tips for Redefining Your Role - The Upside

Transitioning from a solo operator to a scalable business owner requires a deliberate shift in how time is allocated. Erin Halper, founder of The Upside, highlights a common struggle among independent consultants: the "hamster wheel" of juggling too many responsibilities. The core strategy to break this cycle involves a two-part job description exercise. First, document every professional and personal task performed daily, weekly, and monthly, including the time spent on each. Second, draft the job description you actually want, focusing on working on the business rather than just in it. This exercise serves as a catalyst for moving into a new chapter of business growth. The analysis of the current workload should identify tasks that can be delegated or automated. Key questions to ask include what takes the most time, what can be done by others with minimal training, and which tasks are personally loathed. Halper emphasizes that while many things can be outsourced, business development should generally remain with the founder. Examples of high-impact outsourcing include hiring a student for personal errands like driving kids to free up 10 hours a week or using freelancers for social media graphics. For content creation, implementing frameworks can systemize the process to reduce the weekly time commitment. This shift allows consultants to reclaim significant hours that can be reinvested into higher-value activities or personal well-being. By viewing time through the lens of its hourly value, consultants can justify the cost of hiring help to gain back 40 or more hours a month. This approach moves the consultant away from being a technician and toward being a true CEO of their practice.

Knowing the Difference Between Audience and Community - The Upside

Building a successful brand or professional network requires understanding that an audience is fundamentally different from a community. While many organizations and influencers boast large audiences, these groups are often transactional and passive. In contrast, a true community functions as a supportive ecosystem characterized by unique interactivity among its individual members. This distinction is highlighted through the lens of the film Marcel the Shell with Shoes On, where the protagonist realizes that viral fame and thousands of comments do not equate to the deep, meaningful connections found in a community. A community is defined by people on a common journey who prioritize the good of the group as much as their own individual success. It facilitates connectivity that exists independently of the central brand or influencer, allowing members to support one another directly. For professionals, especially those in independent consulting or corporate transitions, being part of a community is the difference between simply surviving and truly thriving. An audience might keep a person on the same trajectory for years, but a community provides the necessary environment for growth and purpose. The Upside serves as a specific example of this model, focusing on helping independent consultants move away from the isolation of corporate life into a collaborative network that offers flexibility, autonomy, and mutual support.

Quality over Quantity: Why Focus Accelerates Growth - The Upside

Business owners often struggle because they spread themselves too thin across too many responsibilities. The primary differentiator between those who thrive and those who struggle is focus. This involves narrowing down to a specific niche, working with clients who value the service, hiring high-quality team members, and maintaining a sustainable business model. Most importantly, consultants should limit their lead generation to only one or two strategies at a time. Many consultants attempt to manage Instagram, TikTok, newsletters, cold outreach, and podcasts simultaneously. While these methods can work, they often lead to burnout and mediocre results. Instead, consultants should select strategies that have worked previously, are enjoyable to execute, and require minimal time. Committing to these chosen strategies for at least six months allows results to snowball. Effective starting points include leveraging existing networks for referrals and posting relevant content on LinkedIn at least once a week. This focused approach frees up time for strategic thinking and leads to higher quality business leads.

How to Prevent Client Ghosting - The Upside

Client ghosting is an unavoidable reality for independent consultants, but it can be significantly reduced through better sales hygiene and psychological awareness. Common reasons for silence include inadequate discovery where the consultant fails to uncover the actual pain point, or engaging with a contact who isn't the ultimate decision-maker. Internal organizational hurdles or a simple lack of urgency often stall projects. Interestingly, ghosting can also stem from a client's sense of shame. If a consultant spends hours on a detailed proposal and the client decides not to proceed, they may feel they have led the consultant on and find it easier to disappear than to deliver bad news. To combat this, consultants should shift their mindset to being on the same team as the prospect, helping them navigate their own internal hurdles to get a deal signed. This involves asking pointed questions about the client's specific signing process and the root cause of their problem. A critical tactic is discussing pricing ranges during the initial discovery call. This allows the consultant to address pushback or budget constraints immediately, preventing wasted effort on a proposal that was never viable. Furthermore, consultants should never simply email a proposal and wait. Instead, they should insist on a separate call to walk the client through the document. This ensures the value proposition is understood and allows for immediate feedback. Finally, persistent follow-up is mandatory, as silence often just means the client is busy or overwhelmed rather than uninterested.

Investing in Yourself: Overcoming Guilt and Achieving Growth - The Upside

Professionals transitioning into independent consulting often face a significant psychological barrier when it comes to spending money on their own growth. This hesitation usually manifests as a deep sense of guilt, where the individual feels that investing in themselves or their business is taking resources away from family or other responsibilities. This mindset can be a major bottleneck for growth because it prevents the acquisition of tools and networks necessary for high-level success. Successful leaders typically view these expenditures not as costs, but as strategic levers. High-impact investments often fall into a few specific categories that provide long-term value. Education and networking, such as Ivy League MBA programs or elite business cohorts, provide access to high-level decision-makers and peer support that isn't available through standard channels. Personal development through 1:1 coaching helps build the confidence and empathy required for effective leadership in complex environments. Operational investments, like hiring a virtual assistant, are essentially trades of money for time. This allows a consultant to focus on high-value strategy rather than administrative tasks. Even aesthetic choices, like professional attire for a big stage, serve a functional purpose by increasing confidence during major presentations. The underlying principle is that spending money is often a necessary prerequisite to increasing earning potential. To overcome the internal resistance to spending, Erin Halper suggests using a structured exercise to unpack the source of the guilt and evaluate the potential return on the investment. Reframing these expenses as business assets rather than personal splurges is essential for anyone looking to scale their consulting practice or achieve a higher level of professional autonomy. By identifying whether an expense is a need or a deserve, consultants can make more objective decisions about their business trajectory.

How to Become an Industry Expert? Embrace Continuous Learning - The Upside

Expertise is defined by the ongoing pursuit of knowledge rather than reaching a static state of total understanding. For independent consultants and business advisors, maintaining expert status requires an insatiable appetite for growth and a willingness to keep asking questions. The Upside community, which includes over 250 top-tier advisors, operates on the principle that the moment learning stops, expertise begins to fade. This perspective reframes the common feeling of not knowing enough. Instead of viewing a knowledge gap as a lack of expertise, it should be seen as the primary driver of professional value. Clients seek out advisors who are committed to staying at the top of their field through constant research and skill development. A consultant who claims to know everything often lacks the structures for continuous improvement, which is a red flag for potential clients. True authority comes from the burning desire to expand one's subject matter expertise and the discipline to learn something new every day. This mindset helps professionals transition from corporate roles into successful independent careers by focusing on flexibility, autonomy, and a purpose-driven approach to their work. Erin Halper emphasizes that recognizing the limits of one's knowledge is actually a hallmark of a high-level advisor. The ability to admit there is more to learn is what separates true experts from those who have plateaued.

Did a Client Ghost You? Try These Outreach Tips - The Upside

Ghosting is an unavoidable part of the consulting process, even when discovery meetings go perfectly and proposals seem aligned with client needs. The typical cycle involves sending a detailed proposal, followed by silence, leading to anxiety and multiple polite follow-ups that often go ignored. To break this cycle, consultants need a strategy that moves beyond being polite and instead uses professional leverage to get a definitive answer. The core recommendation is a specific final follow-up script designed to elicit a quick response. This script works by introducing professional scarcity and a clear deadline. It informs the client that while you were excited to work with them, you now have another proposal out and only have the bandwidth to take on one new project. By setting a deadline, such as the end of the day, and stating that a lack of response will be viewed as a change in their priorities, you reclaim control of the situation. This approach shifts the focus from chasing a lead to managing your own business capacity. Most importantly, consultants should avoid making negative assumptions about why a client has gone silent. In the vast majority of cases, the delay is due to internal client factors that have nothing to do with the consultant's work or value.

Mistakes to Avoid When Building a Community - The Upside

Building a successful community requires unlearning traditional business rules that prioritize rapid scale and hype over substance. The recent controversy surrounding Chief, a network for female executives, serves as a case study for why standard growth tactics often fail in a community context. While FOMO marketing and waitlists can generate initial interest, they lack the long-term substance required to sustain a membership base once the hype fades. Substance and quality must eventually replace the initial excitement of limited spots or exclusive cohorts. A major tension exists between exclusivity and inclusivity. Attempting to market a community as an exclusive club while claiming to value inclusivity is a fundamental contradiction. This approach often leads to widespread rejection among potential members who are denied entry without explanation, undermining the core values of the organization. Furthermore, the pressure of venture capital funding often forces communities to scale too quickly. Unlike traditional tech startups, communities require a longer product-market fit stage because building trust and care takes time. Rapid, VC-fueled growth rarely leads to long-term success in this sector; a slower, more deliberate approach is generally more effective for community health. Marketing strategies that rely on celebrity members or big names often backfire because regular members rarely gain actual access to these individuals. Authentic connection and measurable impact provide more value than superficial optics. Finally, the role of the founder is inseparable from the community itself. While traditional business advice suggests building a brand that can operate independently of its creator, community members are drawn to the specific leadership style, values, and personality of the founder. In a community business, the founder is the brand. Prospective members often research the individual leader before committing to the organization, making personal brand alignment a critical component of the business model.

How to Choose the Right Clients - The Upside

Choosing the right clients is a critical skill for consultants to avoid resentment and lost revenue. The 5Cs Checklist provides a framework for evaluating potential opportunities. Compensation focuses on whether the client can pay the full rate or offer non-monetary value to bridge any gaps. Clout looks at the brand leverage for future deals and whether the company name carries weight in the industry. Clarity involves testing new work types or gaining a better understanding of your own professional preferences. Connections prioritize building valuable relationships that could lead to future growth. Capacity ensures you still have the bandwidth for ideal clients if they appear. An opportunity should meet at least two of these criteria to be worth pursuing. The document also outlines several red flags that signal a poor fit. These include clients who belittle your worth, shop strictly on price, or remain highly disorganized about their own needs. A major warning sign is a prospect who demands agendas, outlines, or specific ideas before signing a contract. This behavior often signals a lack of respect for professional boundaries. Working with the wrong people leads to a lack of referrals, diminished confidence, and a distraction from finding better business. Ultimately, not all revenue is equal. Walking away from a bad fit protects your long-term growth, professional reputation, and mental energy. By using a structured gut check, consultants can ensure their portfolio consists of clients who provide mutual value and support a sustainable business model. The author emphasizes that the wrong clients actually hurt revenue goals by taking up space that could be filled by high-value partners who lead to repeat business and referrals.

Consulting vs Full-time: Making the Right Choice for Your Career - The Upside

Deciding between staying in a full-time role or launching an independent consulting business often comes down to which set of problems you prefer to solve. Consulting offers high levels of autonomy, allowing you to choose your clients, set your own hours, and work from anywhere. It provides the opportunity to build equity and scale your income through self-directed raises and tax-deductible business expenses like co-working spaces, professional memberships, and equipment. This path turns you into a business owner responsible for every aspect of your success. However, this path requires significant self-motivation and the ability to handle sales and marketing. Consultants must also manage their own healthcare, navigate income peaks and valleys, and occasionally deal with the isolation of working in a silo. In contrast, full-time employment provides a predictable environment with consistent paychecks and employer-sponsored benefits. It fosters deep team relationships and offers structured paths for mentorship and training. The trade-off is a lack of control over organizational changes like layoffs, mergers, or acquisitions. Employees are often subject to corporate politics, fixed meeting schedules, and limited flexibility regarding work hours and vacation time. Success in a corporate role is frequently tied to the preferences of a direct supervisor rather than purely individual performance. Even high performers are often dispensable in a traditional corporate structure. The key to making the right choice is identifying which trade-offs align with your current life stage and long-term goals. Consulting favors those who value growth and autonomy over stability, while full-time work suits those who prefer a collaborative, predictable environment. Asking where you want to be in three years can provide the necessary clarity to move forward without regret. Trusting your gut is essential, as the right path is highly individual and depends on your willingness to own your outcomes.

EP 59: Knowing your worth, the… - Women Changing The World - Apple Podcasts

Erin Halper, founder and CEO of The Upside, is a leading authority on independent consulting who has helped thousands of professionals move from corporate roles into independent work. Since starting her company in 2017, she has observed significant shifts in how professionals seek flexibility, autonomy, and purpose. The evolution of The Upside and the broader community business landscape shows how these spaces have matured over time. Professionals are increasingly looking for structured environments that facilitate high-level networking and shared growth. A central theme is the transformative power of focus. Dedicating an entire year to a single, specific area of focus can radically change both a life and a career. This disciplined approach allows professionals to cut through the noise and achieve deeper results than they would by juggling multiple competing priorities. It requires a commitment to saying no to distractions that do not align with the primary goal. Alongside focus, setting firm boundaries is essential for reclaiming time and finding a sustainable balance between professional demands and personal life. These boundaries protect the consultant's most valuable asset: their time and mental energy. For those new to consulting, discovering and owning one's worth is a major hurdle. Moving past the corporate employee mindset to see the true value of independent expertise is a creative exercise that directly impacts pricing and client relationships. Discerning which advice to follow is also critical, as not all guidance applies to the unique path of an independent consultant. Many new consultants make the mistake of taking advice from those who do not understand the independent model. Leading a professional community provides a unique vantage point on industry trends and informs personal growth through a constant feedback loop. By making the right connections at the right time, consultants can accelerate their progress and avoid the typical pitfalls that often derail new independent businesses. This strategic networking ensures that the consultant is positioned within an ecosystem that supports their specific niche and value proposition.

7 Reasons Why Consultants Need PTO Days Too - The Upside

Independent consultants often struggle with the concept of taking time off because they equate hours away from the desk with immediate lost income. This mindset creates a cycle of constant work that leads to exhaustion. Shifting from a monthly or quarterly revenue outlook to an annual perspective allows for a more sustainable approach to business management. By analyzing historical data to identify predictably slow periods, such as August and December, consultants can plan intentional breaks without the associated guilt. This big-picture thinking reframes lower-revenue months as a natural part of a successful annual cycle rather than a sign of failure. Taking this time to reset, reflect, and recharge is essential for maintaining a thriving practice and avoiding burnout. Erin Halper, founder of The Upside, emphasizes that even if a quarter shows significantly lower pipeline activity, the cumulative earnings from stronger quarters often maintain a high monthly average. For instance, if you earn high amounts in the first half of the year, a slower third quarter does not negate that success. Treating yourself with the same professional consideration you would show a full-time employee helps preserve mental energy and long-term business health. The practice of granting yourself permission to disconnect is not just a personal luxury but a necessary business function. It provides the opportunity to reset, reflect, and travel to faraway places, which ultimately benefits the business by keeping the consultant sharp. Reconnecting with yourself and spending quality time with loved ones are critical components of a long-term career strategy. Consistently planning for these breaks ensures that your mental cup remains full, allowing the business to thrive without the risk of the founder burning out. By treating slow summer months as a sign to recharge rather than a reason to worry, consultants can build a more resilient and enjoyable professional life.

Use These 2 Words to Immediately Elevate Your Value - The Upside

Using the phrase starting at when discussing rates is a simple but powerful way for independent consultants to communicate their worth. This approach is more effective than providing a price range because ranges often cap your potential earnings before a project even begins. By setting a floor rather than a ceiling, you leave room for larger projects, higher rates for difficult clients, or testing premium pricing when you have high leverage. Examples include advisory blocks starting at $10,000 or fractional CFO retainers starting at $12,000 per month. This language serves as an immediate filter for prospects. It weeds out companies that cannot afford your services, which saves significant time during the discovery process. It also signals to high-value clients that you are confident in your expertise and have a clear understanding of the market rate for your skills. Publicly listing these starting at prices on a website or services page helps attract the right type of client who respects professional boundaries and value-based compensation.

Here’s How to Sell the Result, Not the Task. - The Upside

Consultants often encounter clients who request specific tasks without fully understanding their own underlying business needs. To move from being a tactical service provider to a strategic partner, you must probe deeper by repeatedly asking why a project is necessary right now. This discovery process uncovers the true motivation, which typically falls into one of the 4 Pillars of Value: increasing revenue, reducing costs, gaining access to specific networks or assets, or removing growth roadblocks. By identifying these core drivers, you align expectations and demonstrate authority before the engagement even begins. Selling the ultimate business result rather than the tactical task builds higher levels of trust and allows for better value communication. If a client asks for a specific deliverable like branding, the goal is to peel back the layers until the conversation shifts to one of these four pillars. This framework ensures that the work performed actually moves the needle for the client's business, making the consultant's value undeniable and easier to justify.

In a Client Lull? Try These 3 Strategies for Growing Your Consultancy. - The Upside

Independent consultants often face market shifts where clients become hesitant, budget-conscious, and risk-averse. Current trends show decision-makers dealing with leadership shuffles, reorganization, and fear of layoffs. To navigate these challenges, consultants should focus on the human element of the sales process. Decision-makers are often motivated by the fear of making a mistake that could jeopardize their bonus or job security. By explicitly prioritizing the client's professional reputation and promising not to let them down, consultants can build the necessary trust to close deals. This involves shifting the pitch from just delivering results to ensuring the stakeholder shines in front of their own peers and superiors. For startup founders, this means addressing their fear that a wrong move could end their funding or business entirely. Another effective tactic involves restructuring service offerings to accommodate tighter budgets without devaluing expertise. Instead of pushing for massive six-figure contracts or high monthly retainers that might trigger internal resistance, consultants can pivot to bite-sized engagements. These include one-time audits, advisory blocks, sprint days, or phased project rollouts. This approach lowers the barrier to entry for nervous clients while maintaining the consultant's hourly or project rates. It allows the client to say yes to a smaller, less risky commitment while still getting the expert help they need to solve immediate problems. This strategy protects the consultant's long-term value while keeping the pipeline moving during slow periods. Flexibility remains crucial during economic uncertainty. Consultants should actively listen for specific pain points, such as internal layoffs or the inability to commit to long-term agreements. These situations actually create opportunities for flexible contractors who can fill gaps without the overhead of full-time hires. By offering short-term, high-impact engagements and pricing them accordingly, consultants can maintain momentum. The core philosophy is to remain empathetic to the client's personal and professional pressures while positioning consulting services as a low-risk, high-reward solution that helps the decision-maker succeed in a difficult environment. Staying open to opportunities slightly outside the typical range can reveal hidden gaps that need filling, allowing the consultant to act as a stabilizing force for the client's organization.

Want More Long-Term Consulting Contracts? Try This. - The Upside

Securing long-term consulting contracts depends heavily on the first thirty days of an engagement. This period is critical because decision-makers often experience immediate doubt after signing a contract. They need validation that they made the right choice. By focusing on exceeding expectations during this initial window, consultants can build massive goodwill, establish deep trust, and encourage clients to provide referrals. Erin Halper, founder of The Upside, emphasizes that coming out of the gate with high intensity is a surefire way to thrive rather than just survive in the independent consulting market. There are five specific tactics to dominate the first month. First, provide a tangible deliverable quickly. This could be a small design, a report, an audit, or a spreadsheet. Seeing something concrete early on provides the client with peace of mind regarding progress and demonstrates immediate value. Second, maintain high responsiveness. Replying quickly to emails signals that the project is a priority. Delays in communication during the first month often lead to client anxiety and a loss of trust. Third, be persistent with follow-ups. Clients are frequently busy and may forget to provide necessary resources. Following up daily until requirements are met demonstrates professional proactivity. While it might feel aggressive, it usually impresses clients with your eagerness to move the project forward. Fourth, prioritize meeting flexibility. Being available for kickoff calls and initial strategy sessions helps build a solid foundation. You can enforce stricter boundaries later, but the start requires high accessibility to accommodate the client's needs. Finally, create and share a specific month one agenda. Outlining the onboarding process and setting clear expectations reduces uncertainty and sets the pace for the entire engagement. This approach shifts the client relationship from one of skepticism to one of confidence. When a client feels seen and heard from day one, they are more likely to grant the consultant autonomy later in the project. This strategy transforms a single engagement into a recurring revenue stream and a source of infinite referrals, accelerating business growth through a simple focus on first impressions.

Experiencing a Client Dry Spell? Take These 5 Steps. - The Upside

Client lulls often trigger feelings of insecurity, such as the urge to lower rates, take on unaligned work, or return to full-time employment. However, these periods provide a valuable asset: time. To capitalize on a dry spell, consultants should focus on five specific areas to ensure long-term growth. First, prioritize business development by reconnecting with former colleagues and engaging in professional communities without a specific sales agenda. This 'seed planting' builds a pipeline for future opportunities. Second, increase visibility through content and thought leadership. Establishing authority builds the trust necessary to attract clients. Third, refine positioning by updating LinkedIn profiles, websites, and elevator pitches to better reflect current offerings and target ideal clients. Fourth, address back-end operations, including SOPs, contracts, and financial tracking, which are often neglected during busy periods. Finally, use the mental space for strategic and creative thinking to rework lead generation plans or reconsider the business's future direction. By shifting the perspective from a lack of work to an abundance of runway, consultants can recharge and prepare for the next influx of clients.

I Quit, But You Shouldn’t. Here’s Why. - The Upside

Erin Halper uses a personal story about her musical ability to highlight how perfectionism stalls professional growth. She can play almost any song on any instrument after hearing it once, yet she quit piano, orchestra, and guitar. She realized she gave up because she felt that if she couldn't be the absolute best, the pursuit wasn't worth it. This master of nothing feeling is a common roadblock for independent consultants who are trying to build their own practices. Halper identifies several ways this perfectionism shows up in the consulting world. Many professionals avoid posting weekly content on LinkedIn because they worry it won't be good enough or their audience is too small. Others play smaller than their potential because they are afraid of failing publicly. This fear also leads to lowering rates because of a belief that clients won't see the value, or avoiding 1:1 coffee chats due to a sense that others won't want to talk to them. Comparing oneself to others who appear to be crushing it only adds to the pressure and leads to self-criticism. The core message is that your business is your instrument. You have to play it loud, practice every day, and accept that your current best is enough. Success in consulting doesn't require being at the very top of a global skill spectrum. There are always clients who are a perfect fit for your specific level of experience and are eager to work with you. Halper suggests that her own talent became a roadblock because it stopped her from learning traditional skills like reading music. Instead of quitting when the traditional path didn't fit, she encourages consultants to find their own unique way forward. The focus should be on consistency and owning your specific path rather than giving up when you don't meet an impossible standard of perfection.

This One Approach Will Help You in Any Difficult Client Conversation - The Upside

Meaningful professional relationships require conflict to grow deeper. The core philosophy presented by Erin Halper suggests that conflict creates intimacy. When handled with a human touch, disagreements lead to more fruitful and resilient partnerships. The primary strategy for navigating these moments is to speak from the heart. This approach signals mutual respect and breaks down the barriers of transactional communication. It moves the conversation away from a purely business exchange and into a human-to-human interaction. In practice, this involves using a specific opening line: 'I respect and treasure our relationships so much. Can I speak from the heart for a moment?' This phrase serves as a pattern interrupt to standard corporate jargon. It allows a consultant to express feelings and concerns directly while positioning themselves as an ally. This method is particularly effective for difficult scenarios like raising rates, addressing project friction, or resolving unspoken tensions. By being transparent about how a situation makes you feel, you invite the client to see the human impact of the business relationship. By moving away from cold, formal language like 'per our previous conversation,' professionals can build impenetrable relationships. Speaking from the heart creates the mental space needed for honest dialogue. It invites the client to provide advice and collaborate on a solution rather than becoming defensive. Erin Halper, founder of The Upside and an authority on independent consulting, emphasizes that this authenticity is essential for professionals transitioning from corporate roles to autonomous careers. The goal is to replace rigid professional distance with authentic connection to ensure long term success. This approach fosters a sense of being on the same side, which is critical for high stakes consulting engagements where trust is the primary currency.

This One Industry Gets Value-Based Pricing Right - The Upside

Transitioning from hourly billing to value-based pricing allows experienced consultants to earn significantly more in less time. The wedding industry serves as the prime example of this model because it prices based on the high stakes and emotional significance of the event rather than the raw materials provided. A wedding dress is sold as a generational memory and a cake is sold as a symbol of status and personality. This shift moves the focus from the physical product to the long-term value and setting of the most important day of a client's life. Value-based pricing is fundamentally built on desired end-results instead of the process or time spent. It ensures that a professional is paid for the 25 years of experience that allows them to produce a brilliant idea in 25 minutes. This approach rewards talent, efficiency, accuracy, and wisdom. By decoupling income from hours worked, consultants can level up their business and get paid for the true impact they deliver to their clients.

Service Offerings All Over the Place? Try This 3-Tier Approach. - The Upside

Consultants often struggle with a lack of intentionality in their service offerings, frequently presenting an overwhelming menu that confuses potential clients. To capture more leads and close contracts effectively, consultants should adopt a strategic prix fixe approach using a three-tier Small/Medium/Large (S/M/L) model. This structure leverages client psychology to provide clarity and alignment, making it easier for prospects to identify which offering fits their specific needs. The S/M/L framework can be applied across different dimensions. Pricing-based tiers allow consultants to accommodate various budget levels, such as offering a low-cost sprint day, a mid-range audit, and a high-end custom project. Alternatively, tiers can be structured around client stages, moving from startup advisory to growth-stage support and eventually full-service coaching. Another dimension is access, where tiers range from group programs to bespoke 1:1 sessions. Finally, the model can be used to build trust by offering a low-friction entry point, like a two-hour advisory block, before moving into longer-term monthly retainers. By limiting choices to exactly three options, consultants reduce decision fatigue and simplify the sales presentation. Even if a client requires a custom solution, having these predefined tiers provides a solid baseline for adjustments and pricing. This methodology ensures that the consultant appears organized and strategic while allowing the client to feel catered to through intentional service design.

Every Business Owner Should Take an RV Trip. Here’s Why. - The Upside

Erin Halper uses a family RV trip to Niagara Falls as a framework for running a successful consultancy. The experience highlights three core pillars: preparation, flexibility, and resilience. Effective planning involves deep market research and a solid business plan before launching services. Just as packing a small vehicle requires precision, a business needs a strong foundation to minimize early mistakes. However, planning has limits. Business owners must stay flexible as the economy shifts or personal goals change. The consultancy model is constantly in motion, requiring pivots and scaling when offerings become stagnant. Finally, the reality of entrepreneurship involves significant highs and lows. While the autonomy and purpose of consulting are rewarding, they come with inevitable setbacks and messy moments. Success depends on maintaining resiliency through these cycles and accepting that the journey will not be a perfect highlight reel.

How This Community Got Insanely Engaged - Interview with Erin Halper CEO of The Upside on Circle

How Erin Halper Is Empowering Independent Consultants Worldwide | Nasdaq

Erin Halper, CEO of The Upside, shares her journey of creating a global community for independent consultants. The business started in 2017, inspired by her need for flexibility while her son underwent heart surgeries. Halper realized that many professionals leave their careers due to a lack of control over their schedules, and she built The Upside to help them launch and scale their own consultancies. In 2023, the community generated an estimated $40 million in economic advancement for its members through referrals and knowledge sharing. Halper attributes her success to staying niche and avoiding the trap of scaling too quickly. She famously took the company off Instagram in 2022, finding that it freed up resources without hurting growth. After a period of burnout in 2022, she hired a strategist for a full audit. This move allowed her to double her EBITDA while cutting her working hours in half. Her definition of success has evolved from revenue and ego metrics to a lifestyle focused on fulfillment and time for volunteering.

Exposure Is Not Compensation Unless You Do This - The Upside

The common corporate refrain that exposure serves as compensation for workshops or keynotes is fundamentally flawed because exposure does not pay bills or reflect the value provided to clients. Speaking for free is only justifiable under very specific conditions. These include when the audience consists entirely of a primary target market and there are ample opportunities for direct networking with decision-makers. Outside of these scenarios, uncompensated speaking rarely converts into paid business. When faced with a no pay policy, consultants have three primary paths. The first is a graceful refusal that leaves the door open for future budgeted opportunities. This maintains professional dignity and reinforces the value of one's time. The second path involves direct pushback by questioning the discrepancy between a company's high revenue and its refusal to pay experts. This can include asking for data on how previous uncompensated speakers benefited from exposure or highlighting contradictions in the company's stated pay equity and diversity goals. The third path is negotiating creative, non-monetary alternatives that provide tangible business value. These include securing written permission to use the corporate logo for social proof, obtaining rights to film the presentation for a professional speaker reel, or requiring the company to cover all travel and lodging expenses. Other high-value trades include bulk book purchases for employees, bartering for the company's products or services, or gaining access to the organization's media channels, such as podcast appearances or ad placements. The goal is to ensure the consultant feels valued and receives a return on their expertise that aligns with their current business stage and goals. Creative bartering, such as requesting high-end products or media spots, can often bridge the gap when a cash budget is unavailable. Ultimately, the decision to speak should be based on a clear exchange of value rather than vague promises of future visibility.

Debunking the Myth of Passive Income - The Upside

Passive income is often marketed as a quick or simple way to generate revenue, but building a viable stream is an intensive process requiring significant time, investment, and energy. The reality of these models is captured by the acronym TIRED: Time, Investment, Resources, Energy, and Determination. Most gurus fail to mention that these streams are rarely passive in the beginning. Membership businesses are not set-it-and-forget-it models. They require constant value creation and active retention efforts to keep members from churning. Success in this area depends on a genuine passion for community building rather than just a desire for automated revenue. Similarly, digital courses demand high upfront costs and long development cycles. For example, The Upside invested over $100k and 18 months before seeing results. Success in courses depends on aggressive marketing, including hosting dozens of live webinars, frequent social media posting, and paid ad strategies. A course only becomes truly evergreen after years of building a reputation and a large enough audience to sustain it. Paid downloads and gated content also fail without a pre-existing, loyal audience. Instead of charging for downloads, offering them for free can help build a newsletter audience. This is a more valuable long-term asset because you own the list, unlike social media followers. While paid newsletters can generate significant revenue (for instance, 5,000 subscribers at $4.99 a month equals $25k in monthly revenue), reaching that scale is a main business function, not a side supplement. The if you build it, they will come mentality is a fallacy in the digital product space. Most passive income streams only become truly passive after years of active audience building and reputation management. Consultants should evaluate if they are willing to commit to the years of effort required before pursuing these models, as they often require a different skill set than traditional advisory work.

When You’re Ready to Grow, Focus on These Three Words - The Upside

Business growth often stems from subtraction rather than addition. The edit to expand philosophy, shared by Pamela Pekerman and implemented by Erin Halper at The Upside, suggests that consultants and entrepreneurs achieve better results by narrowing their focus. Halper notes that 2023 was her most successful year specifically because she pruned several core areas of her business operations. This process involved limiting her social media presence exclusively to LinkedIn to meet her audience where they already congregate. She also restructured her team by moving away from expensive external agencies and instead investing in high-quality in-house talent. Calendar management played a vital role in this expansion. By setting a hard stop for meetings at 2:30 pm, she reclaimed time for creativity and strategic thinking. She also eliminated 1:1 calls from her lead generation strategy to prevent them from cannibalizing her schedule. This shift required getting extremely clear on her specific offerings and moving past the constant testing phase of product-market fit. Instead of chasing new trends or launching multiple services, she focused on building upon what was already proven to work. Many independent consultants fall into the trap of adding more services, more audiences, and more virtual assistants in hopes of scaling. This often leads to a cycle of constant testing and starting over. The edit to expand approach argues that energy spent on editing is more productive than energy spent on adding. By refining a team, funds are allocated only to those who provide time back to the founder. By refining offerings, a consultant avoids the exhaustion of perpetual launching. Ultimately, the framework serves as a reminder that more is rarely better in the context of professional services and that true expansion requires the discipline to do less.

Why Clients’ Budgets Have Nothing to Do with Your Pricing - The Upside

Consultants often encounter clients who lack a clear understanding of what specialized expertise costs. Unlike full-time employees, consultants do not receive benefits like healthcare, vacation, or equity, and they must cover their own business expenses. Because of these factors, consulting rates are not comparable to corporate salaries. Pricing should be based on the specific value delivered rather than an arbitrary budget number provided by the client. Many clients set budgets based on internal benchmarks that do not reflect the market reality of expert advisory services. To move away from budget-led pricing, consultants should focus the discovery phase on uncovering the true business impact of the work. This involves asking targeted questions about the client's goals, why they cannot solve the problem with internal resources, and what they stand to lose if they take no action. When the client realizes that a project could lead to significant revenue gains or prevent major losses, the consulting fee becomes a strategic investment. For instance, a $65,000 fee is easily justified if it secures a $2M return. Introducing pricing early with a range helps anchor the conversation and gauge the client's fit. By stating a typical price range and then pausing for a reaction, consultants can identify if the client is serious before drafting a formal proposal. If the client pushes back on the price, the consultant should redirect the conversation to the ROI and the cost of inaction. Ultimately, maintaining personal conviction in one's pricing is essential because clients will mirror the consultant's confidence in the value being offered.

What 6 women learned about starting a business midlife

Entrepreneurship is often seen as a young person's game, but data suggests otherwise. A 2018 study found the average age of U.S. entrepreneurs is 42, rising to 45 for the fastest-growing startups. Currently, Gen X women make up 69% of female business owners. This shift is driven by several factors unique to midlife. Founders like Judy Schoenberg and Linda Lautenberg of Evolve.Me highlight that midlife often brings more free time and a stronger sense of urgency to pursue long-held dreams. Unlike younger founders, those in their 40s and 50s benefit from deep professional networks and established financial stability, which actually lowers the relative risk of starting a venture. Erin Halper, founder of The Upside, notes that midlife entrepreneurs make decisions faster because they rely on years of experience rather than trial and error. For many, starting a business is also a response to corporate ageism and burnout. Raksha Shah, who started a nutrition practice at 65, found entrepreneurship to be a viable alternative to high-pressure biotech roles where older workers often feel undervalued. This stage of life also fosters greater resilience. Having navigated previous career setbacks, these women are more comfortable with the ups and downs of building a company. Ultimately, midlife entrepreneurship allows women to define success on their own terms, whether that means hitting high revenue targets or prioritizing flexibility and a 20-hour work week.

Here’s How to Get Paid on Time, Every Time - The Upside

Securing timely payments as a consultant requires proactive structural changes to your billing process rather than just reactive chasing. Start by requiring upfront payment for all work, whether through a monthly retainer or a significant portion of a project fee. This shifts the risk away from the service provider and ensures that the client is financially committed before resources are allocated. Reducing friction is equally important for accelerating cash flow. Implementing click-and-pay buttons or accepting credit cards can eliminate the turnaround time associated with traditional checks or bank transfers. While credit cards involve a 3% fee, this can be offset by a slight price increase and is often cheaper than the administrative cost of following up on late invoices. For larger clients with rigid net-60 or net-90 terms, consultants should negotiate for a net-30 minimum. Decision-makers often have the authority to override standard corporate policies for independent contractors if they are motivated to start the project. Identifying and building a direct relationship with the specific person in the accounts payable department is a critical step that many consultants overlook. Sending a small introductory gift to the person processing the payments can prioritize your invoice in their queue and build a human connection that transcends the digital invoice. If an invoice becomes overdue, daily follow-ups are necessary and professional. The squeaky wheel approach ensures the client prioritizes the debt over other competing obligations. If payment remains outstanding, consultants have the right to stop work immediately and withhold final deliverables until the balance is cleared. This provides a tangible incentive for the client to resolve the issue. Late fees are generally discouraged for independent consultants because they are difficult to enforce and can damage the long-term relationships that drive repeat business. Instead, focus on clear communication and operational boundaries to ensure you are paid on time, every time.

Here’s How to Shift Your Mindset on Hourly Rates - The Upside

Selling your time is a trap for high-level experts. When a client asks how many hours a project takes, they are looking at the wrong metric. The real value lies in the years of experience that allow an expert to solve a problem in ten minutes rather than ten days. This is illustrated by the story of an electrician who charges $1,000 for a ten-minute fix. The cost isn't for the labor; it's for the knowledge of which specific wire to cut to prevent a fire. Consultants should stop penalizing themselves for being efficient. If a result is delivered faster, it's often more valuable to the client, not less. The EARNED framework helps categorize this value: Experience, Access, Relationships, Niche expertise, Efficiency, and Decisiveness. These elements represent the accumulated know-how that a client is actually buying. Shifting to this mindset allows for higher margins and better alignment with client goals. Instead of counting hours, focus on the impact and the ease with which you deliver results. This approach builds a business that respects your expertise and provides more freedom.

Why so Expensive? Because You’ve Earned It. - The Upside

Pricing your time as a consultant requires a mindset shift away from hourly rates toward the inherent value of your relationships and access. Many professionals overlook the fact that a single introduction can be worth five or six figures to a client. For example, a finance professional named Frank once earned $80,000 for a single email introduction that led to a multi-million dollar investment. While the physical act of sending the email and attending a meeting took very little time, the value lay in the years spent building the relationship that made the introduction possible. Without that specific connection, the company could not have brought its product to market. Consultants often bring high-value access to talent, investors, editors, publishers, partners, sponsors, and buyers. When setting prices for projects or retainers, you should consider what it would cost a company to build these connections from scratch and the total impact those connections will have on their business growth. If a client pushes back on pricing, the focus should remain on the immense value and long-term impact that years of experience and a vast network provide. Access is a premium asset that justifies higher rates because it provides a shortcut to results that the client cannot easily replicate on their own.

Here’s What You Need to Unlearn from Your Corporate Days - The Upside

Transitioning from a corporate environment to independent consulting requires a fundamental shift in how you present yourself. Corporate culture often demands conformity to a specific image of professionalism, but this approach usually fails in the independent market. Sticking to rigid corporate standards often prevents you from standing out, building genuine relationships, or attracting the right clients. Instead of following the corporate playbook, success comes from leaning into your own personality and voice. This involves replacing stiff corporate lingo with human conversation and sharing personal anecdotes that break down barriers. Even if communication isn't perfectly polished by academic standards, a conversational tone is more effective at sparking engagement. Showing up as a full person, including being open about hobbies and family, creates a unique superpower because no one else can replicate your specific identity. While some consultants fear that straying from corporate norms will alienate clients, the opposite is true. Clients hire individuals because they want to work with that specific person. If there is no personal connection, the quality of the work matters less. Authenticity acts as a magnet, drawing clients in and making them appreciate the consultant more. Embracing mistakes and being human makes you relatable rather than just another service provider.

Sometimes Less Leads to More - The Upside

Many people think that more offerings lead to more success, but a better strategy focuses on making the most money with the least effort in the shortest time. This anti-struggle philosophy suggests that the easiest way to fix a consulting business is to cut the number of revenue streams. Many independent professionals try to manage a community, group coaching, corporate consulting, and 1:1 advisory all at once. Even if you are talented enough to do it all, it is rarely a good idea. Each model needs its own messaging and marketing, and they often target different audiences. This forces you to constantly switch contexts, which leads to burnout. When you try to be everything to everyone, you end up stretched too thin to do anything exceptionally well. The best move is to audit your offerings and pick one or two models to dive into deeply. You should choose based on what feels most exciting and aligned with your strengths. Ask yourself which work feels like drudgery and which work doesn't really feel like work at all. Focusing on what lights you up is a strategic choice to keep the business profitable and sustainable over the long haul. Editing down to a single main model brings less stress, fewer meetings, and a shorter work week. It also lowers your overhead and makes your marketing much easier because you only have one story to tell. This focus eventually leads to a higher EBITDA because the business becomes much more efficient. By going all in on your best offerings, you can build a business that is more enjoyable and grows faster than one weighed down by too much complexity. This approach allows you to reclaim your time while actually increasing your bottom line.

If You’re Still Charging by the Hour, Read This. - The Upside

Transitioning from hourly billing to value-based pricing requires a fundamental shift in how consultants view their own expertise. The core of this argument is illustrated by the story of Paula Scher, a branding expert who famously sketched the Citigroup logo in just five minutes on a napkin. Despite the nearly instant execution, the agency charged $1.5 million for the work. This example highlights that clients are not paying for the minutes spent on a specific task. Instead, they are paying for the decades of experience, trial, and error that allow an expert to reach the right solution with such speed and precision. The EARNED framework is introduced as a tool for consultants to articulate and defend their worth. This acronym stands for Experience, Access, Relationships, Niche & know-how, Efficiency, and Decisiveness. These six elements represent the actual assets an independent professional brings to a client engagement. When a client pushes back on a project fee by asking for an hourly breakdown, the consultant should pivot the conversation. The response should emphasize that the fee covers years of training, leadership, and specialized knowledge required to ensure the final deliverable is exactly what the client needs, regardless of how long it takes to produce. Ultimately, efficiency should be treated as a premium rather than a penalty. Charging by the hour creates a misalignment of incentives where the most skilled professionals are paid the least for their speed. By decoupling fees from time, consultants can capture the full value of the results they provide. This approach builds the confidence necessary to maintain high-ticket pricing and reinforces the idea that a consultant's unique professional history is their most significant competitive advantage.

Age Can Be Your Competitive Advantage - The Upside

Consulting is one of the few industries where getting older actually increases your market value. While corporate environments might make professionals over 40 feel less relevant, independent consulting prizes the gray hair and wrinkles that signal deep expertise. Clients view older consultants as decisive leaders who have already navigated complex problems and possess a vast network of contacts. They are seen as unentitled doers who know exactly what will work and what won't before the project even starts. The EARNED framework summarizes this competitive edge through six specific pillars. Experience represents the years spent in the field. Access and Relationships highlight the valuable network and resource treasure trove a senior professional brings. Niche and know-how focus on specialized expertise. Efficiency and Decisiveness show that a veteran can solve problems faster and with more confidence than a junior counterpart. Even though senior consultants command higher rates than younger freelancers, the right clients are willing to pay for the certainty of results. The document provides specific scripts for handling price objections. If a prospect balks at the price, the best approach is to stay professional and suggest they look for a junior freelancer if they are strictly budget-focused. One suggested response involves telling the client that if a lower-budget option doesn't deliver the quality they need, the door remains open for a future conversation. Another tactic is to offer to help them find a part-time freelancer or recent grad who might fit a junior-level budget. This maintains the consultant's premium positioning while keeping the door open for when the client eventually needs higher quality work. Ultimately, owning your age as a strength allows you to command higher fees and work with clients who value outcomes over hourly costs.

This Is Why You Should Want More No’s - The Upside

Business development often stalls because of a natural fear of rejection and the discomfort of making big asks. Celi Arias, an experienced business builder, suggests a counterintuitive strategy: challenge yourself to collect as many no's as possible. This mindset shift removes the pressure of landing a yes and encourages a higher volume of outreach. When the goal is simply to ask, the fear of the outcome diminishes, which eventually leads to the desired results. Sally Joy Wolf is a prime example of this philosophy in action. Her willingness to face potential rejection led to phone calls with Anderson Cooper about his podcast, a feature in Oprah Daily, and free entry to invite-only conferences. The strategy applies to several high-impact business activities. These include pitching media outlets, building relationships with dream companies, increasing LinkedIn visibility, and applying for industry awards. It is also a powerful tool for raising prices or launching new products. By gamifying rejection, professionals can push past the courage gap and unlock opportunities that previously felt out of reach. The core idea is that you have significantly more to gain by asking than you have to lose by hearing no.

Here’s How to Avoid Giving Away Ideas for Free - The Upside

Consultants often fall into the trap of sharing their best ideas during discovery calls to prove their competence or win over a skeptical prospect. This habit typically backfires because it devalues the consultant's primary product: their expertise. When a client receives a specific solution for free, they often perceive the problem as easier than it actually is, leading them to attempt the work in-house or hire a cheaper resource for execution. Furthermore, over-sharing can signal a lack of confidence, as it suggests the consultant feels they must "audition" with free work to justify their fees. The most effective way to navigate these conversations is to focus on the "what" while withholding the "how." This framework allows a consultant to outline the strategic direction and expected outcomes without revealing the specific tactical steps required to get there. For example, a consultant might suggest developing out-of-the-box social media campaigns and strategic influencer partnerships to drive conversions. This provides a clear vision of the project's scope. In contrast, sharing the specific names of influencers or the exact narrative arc of a video campaign gives away the "how," which is the proprietary value the client should be paying for. If a prospect pushes for more granular details during the sales process, the consultant should use a scripted pivot. This involves expressing excitement about the ideas they have while clarifying that these specific insights are the core of their paid service. By stating that this level of detail is exactly what clients hire them for, the consultant reinforces their professional value and maintains the integrity of their intellectual property. This approach shifts the focus from the immediate "free advice" to the consultant's history of delivering results and exceeding goals for other companies. Ultimately, protecting these ideas ensures that the discovery phase remains a tool for qualification rather than a source of free labor.

Keep Your Eye on Your Why - The Upside

Erin Halper recounts a transformative experience from her college years that reshaped her entire philosophy on career and success. While studying for a business degree with aspirations of corporate prestige, she took a babysitting job for an exceptionally wealthy family in suburban Washington, DC. This family lived a life of extreme luxury, complete with private jets and personal chefs, yet they were visibly miserable. Halper observed that the children were raised by a rotating staff and the parents were unhappy, which led her to question her own goals of obtaining fancy titles and office spaces just to impress others. She identifies a destructive cycle where the pursuit of status is often a mask for insecurity. In this loop, a person seeks external validation to feel worthy, but because that validation comes from outside rather than within, it is never sufficient to provide lasting peace. This realization prompted her to pivot away from traditional corporate ladders toward a more purpose-driven path. Ten years later, a chance encounter with the father of that family confirmed her insights; despite his status, he did not even recognize her, highlighting the fleeting and impersonal nature of that world. Today, Halper leads The Upside, a community dedicated to helping professionals transition into independent consulting. She encourages people to look past the paycheck and interrogate their deeper motivations. By asking why success is important or why someone wants to own a business, she helps them find the flexibility and autonomy that corporate roles often lack. The focus is on keeping your eye on your why to ensure that professional achievements actually lead to personal fulfillment.

If You Want to Know What It’s Like at a Company, Ask This Person - The Upside

Evaluating a company's true internal environment requires looking beyond management's perspective. Just as restaurant bussers know which dishes are actually good by seeing what's left on plates, entry-level staff see the unvarnished reality of leadership and culture. Entry-level employees, interns, and assistants bear the brunt of poor management or benefit most from healthy cultures. These individuals observe the day-to-day reality quietly and are often aware of internal gossip and organizational weaknesses that leadership might hide. They see which projects are actually moving and which ones are stalled by bureaucracy. Visible issues at the ground level, such as unhappy retail staff, poor maintenance, or disorganized workflows, often predict toxic corporate office environments. For consultants and job seekers, the most reliable way to gauge how they will be treated is to speak with those at the bottom of the hierarchy. Their experience provides a reflection of the company's actual values and management style. This approach is particularly useful for independent consultants who need to vet potential clients before committing to a contract. By asking the right questions of junior staff, you can identify if a company has a lack of pride or if leadership is a nightmare to work for. Those at the bottom of the ladder often know exactly who the good managers were and who the nightmares were. They can identify the weakest links in the company and know the gossip on everyone. This ground-level perspective is often ignored by those at the top but is essential for anyone entering the organization from the outside. This due diligence helps avoid situations where you might join a company only to leave shortly after due to cultural misalignment. The busser method shifts the focus from polished executive pitches to the lived experience of the workforce.

Results Vs. Vehicles: How to Sell the Whole Package - The Upside

Selling consulting services effectively requires a balance between the results you deliver and the specific vehicle you use to get there. Most consultants focus on results, which usually fall into one of the Four Pillars of Value: growing revenue, cutting costs, providing access, or solving growth-stifling headaches. While these results are what clients ultimately buy, they are often generic and shared by many competitors. To stand out, you have to clearly define your vehicle, which is the unique methodology, toolset, or approach you use to reach that destination. For example, while two consultants might both promise to drive sales for B2B SaaS startups, one might use SEO as their vehicle while the other uses social media ads. Defining the vehicle is crucial because it differentiates you from others who offer similar outcomes. It provides a clear answer to why a client should choose you over another expert. The vehicle could be a specific technology like automation, a community-based model, or a proprietary framework. By articulating both the result and the vehicle, you can communicate your value more easily, project higher confidence, and avoid being seen as a commodity. This approach moves the conversation away from just the what and into the how, which is where the true value of an expert lies. The process of identifying these elements involves a simple exercise: identifying the specific problem solved, the tangible result achieved, the method of delivery, and the emotional state of the client after the engagement. This clarity helps in crafting better LinkedIn headlines and sales pitches that resonate with specific target audiences. When you are clear about your vehicle, you can stop competing on price and start competing on the effectiveness of your specific process. This framework is especially useful for independent consultants looking to transition from corporate roles into high-value advisory work.

Lack of Confidence? May Be Time to Unlearn Everything. - The Upside

Corporate environments often function through power dynamics that systematically erode individual confidence. This erosion happens through what can be described as death by a thousand papercuts. These are small, repeated instances where employees are told they aren't ready for promotions, denied promised raises, or discouraged from sharing salary information with their peers. These tactics allow employers to maintain the upper hand and maximize profit by keeping talent feeling replaceable and powerless. After a twenty year career, many professionals struggle to identify their intrinsic value outside of an employer-employee relationship. They end up asking who they are without their title or company name. For those transitioning into independent consulting or fractional leadership, this lack of confidence becomes a significant barrier to growth. Success in the independent market requires high levels of self-assurance across several specific pillars. These include how you package your services, how you conduct pricing discussions, and how you lead discovery calls. It also extends to how you position yourself on LinkedIn and how you set firm boundaries with clients. When a consultant lacks confidence, it creates a ripple effect. If you don't show up with authority, your dream clients won't have the confidence to hire you. The unlearning process involves recognizing that past corporate feedback was often a manipulation tactic rather than an objective assessment of your skills. Rebuilding this professional identity requires a total shift in your immediate environment. Surrounding yourself with a supportive community is essential for highlighting your brilliance and counteracting years of corporate conditioning. This shift allows you to show up as the expert you actually are. The transition from corporate life to autonomy is not just a change in how you get paid. It is a psychological shift from being a managed resource to being a high-value expert who controls their own worth.

It May Be Time to Meet Clients Where They Are. - The Upside

Erin Halper explains the evolution of her company, The Upside, which originally launched in 2017 as a matching service between companies and consultants. Despite her skill in client acquisition, she found herself struggling to sell high-cost talent to companies while simultaneously managing a waitlist of 500 consultants eager for work. This imbalance signaled that her business model was misaligned with actual market demand. She pivoted to make consultants her primary customers, which led to the company's success. This story serves as a lesson for independent consultants who may be forcing a service model that the market is not ready to buy. The core advice is to analyze the gap between who you attract and who you actually monetize. Consultants should look closely at their discovery calls and ask specific questions. What are clients actually asking for? Is there a difference between what they say they need and what they actually need? Are you turning people away because they want something outside your current scope? If discovery calls frequently end in rejection due to high prices or long timelines, it indicates a need for more flexible offerings. Halper suggests creating scaled-down versions of services, such as one-hour paid advisory calls or VIP days, to make expertise more accessible to those who cannot commit to a full engagement. Additionally, if clients request services outside a consultant's core scope, subcontracting allows the consultant to maintain the relationship and monetize the opportunity without performing the labor themselves. This keeps the client in your orbit while providing a new revenue stream. Consultants are encouraged to look for patterns in their lost business rather than viewing every rejection as a failure of the prospect. While maintaining high standards and pricing is valuable, ignoring consistent feedback from the market can stall growth. Meeting clients where they are might involve breaking down large projects into smaller, phased purchases. This approach allows clients to commit to a portion of the work at a time, lowering the barrier to entry and building trust for future high-ticket engagements. By adjusting the model to fit the actual needs expressed in discovery calls, consultants can unlock growth and better serve their target audience.

This One Strategy Helps Consultants Stay Perpetually In-Demand - The Upside

High demand consultants differentiate themselves by offering access rather than just effort. This strategy flips the traditional sales dynamic, putting the consultant in control of their pipeline and allowing them to vet clients instead of being vetted. Access can take many forms, including direct relationships with buyers, proprietary frameworks, hard to find talent, or proven systems with repeatable results. When a consultant positions themselves around access, they create a sense of exclusivity that justifies premium pricing and long term engagements. The fashion showroom model illustrates this concept well. Designers must often prove their line is worthy before being accepted as a client, then pay high monthly retainers for the showroom's relationships with store owners. Similarly, successful investors like Mark Cuban use their personal networks as leverage to win deals, offering a direct line to key decision makers that others cannot provide. This creates a scenario where the guest often gives up more equity just for the privilege of that specific connection. In contrast, consultants who lead with hustle often find themselves competing on price and flexibility. While they may be highly skilled, the perception of their value is lower because they are selling their labor rather than their unique entry points. The difference is highlighted by comparing two PR consultants: one who sells her deep Rolodex of media influencers and editors, and another who promises to work hard and knock on doors. The former can command five figure monthly retainers and be highly selective, while the latter must constantly hunt for new business and remain flexible on pricing. Moving toward the access end of the value spectrum requires identifying specific assets like industry insider connections, funding sources, or unmatched expertise that a client cannot easily replicate. This shift allows consultants to move away from the constant grind of business development and toward a model where they are perpetually in demand.

How to Manage When Clients Leave - The Upside

Erin Halper, founder of The Upside, addresses the emotional and strategic challenges independent consultants face when clients leave. As a consulting business grows, it inevitably undergoes changes such as reworking payment terms, tightening boundaries, changing offerings, or raising prices. These evolutions often lead to the departure of long-term clients who may not align with the new direction. This churn frequently triggers a fear response in consultants, leading to anxieties that they are the problem, that no one else will want to work with them, or that the business will fail. Halper argues that these fears are usually unfounded and that client departures are a natural part of a business's lifecycle. The reasons for a client leaving are often rooted in the client's own situation rather than the consultant's performance. Some clients are resistant to change, prefer the previous version of the service, or are operating with a scarcity mindset. In other instances, clients cycle out elegantly because their needs or budgets have changed, or because the consultant has successfully helped them reach a level where they no longer require the same support. This cycling out is a sign of success, as it means the consultant has delivered the intended value. The core message is that change is a necessary component of growth. Consultants must accept that not every client is meant to be part of every chapter of their business journey. By letting go of clients who no longer fit, consultants create the necessary space and capacity to attract new clients who are better aligned with their evolved pricing, expertise, and service model. Overcoming the fear of loss is essential to avoid stagnating and to ensure the business continues to move forward.

Here’s What Fast Fashion Has to Do with Your Consultancy - The Upside

Erin Halper explores how the fast-fashion giant ASOS uses specific psychological and operational strategies to drive massive growth, and how these same principles apply to independent consultants. The core idea is that positioning and momentum are just as critical for solo experts as they are for retail giants. Branding should be intentional. Even for a solo practice, having a formal name, a clean one-page website, and a professional LinkedIn banner creates the perception of a legitimate company rather than just a freelancer. Visuals and positioning matter because they set the tone for the client's experience before a conversation even starts. Instead of discounting services, consultants can create FOMO through time-sensitive incentives. This includes offering extra advisory hours, 1:1 time, or preferred pricing that locks in current rates before a scheduled increase. A Good Until date on proposals serves as a functional countdown clock. This protects the consultant's schedule and forces the client to move quickly or risk losing the quoted price and the consultant's availability. The proximity effect is a powerful positioning tool used by ASOS to sell high-margin items by placing them near designer brands. For consultants, this means associating with high-profile experts, speaking on panels, or showcasing big-name client logos. A consultant's perceived value increases through association with those already playing at a high level. Social proof, specifically through consistent LinkedIn content and building a following, creates a visible track record that leads to inbound opportunities and press features. Finally, speed is a major differentiator. ASOS wins by moving fast, and consultants should do the same. Delivering proposals within 24 hours and having a seamless, click and pay onboarding process prevents deals from stalling. Being highly responsive and having a kickoff process ready to roll the day a contract is signed demonstrates a level of professionalism that many larger agencies fail to match.

Permission to Leave Behind What Isn’t Working - The Upside

Erin Halper, founder of The Upside, stopped posting on her company's Instagram in 2022 after realizing the platform provided almost no return on investment. Despite spending $5,000 per month on reputable agencies and several hours a week of her own time, the account only brought in one or two members per quarter. The decision to quit was difficult because of the perceived need to look like a real company with a large following. However, the effort created significant mental noise and took up too much headspace without yielding results. Halper shifted her focus to LinkedIn, where her target audience of independent consultants actually spends time. While LinkedIn was considered less visually appealing at the time, focusing on personal stories and short-form content there built significant momentum. Currently, most new members of The Upside come through her LinkedIn content or her Wednesday Wisdom email list. Instagram is now used only for personal inspiration and leisure rather than business growth. The narrative serves as a framework for other business owners to evaluate their own shoulds. It encourages leaders to identify which activities are weighing them down and to give themselves permission to walk away from strategies that do not serve their specific goals. The juice worth the squeeze test helps determine if the time, money, and mental energy spent on a channel actually translate into tangible business growth.

Do This When a Client’s Budget Is Grossly Misaligned - The Upside

Budget misalignment in consulting often occurs when a client proposes a fee that is significantly lower than a consultant's standard rate. For instance, a client might offer $500 for a one-hour workshop when market rates for experienced advisors typically range from $2,500 to over $10,000. This discrepancy usually happens because in-house teams do not understand how consulting services are priced. They often view a fee as a simple hourly rate rather than a reflection of the value delivered. A consultant's fee covers much more than the time spent speaking. It includes the preparation hours required to tailor the content, the years of experience used to develop unique frameworks, and the long-term impact the session will have on the organization. To handle these situations professionally, consultants can use three primary strategies. First, they can bundle the small request into a larger engagement. By explaining that they do not take on one-off workshops, the consultant can pivot the conversation toward a more comprehensive package that provides higher value to the client and meets the consultant's minimum project requirements. Second, the consultant can be direct about their pricing floor. Stating that engagements start at a specific dollar amount allows the client to look for additional budget or suggest creative non-monetary compensation. It is vital to avoid taking a low fee based on the promise of future work, as this rarely results in a profitable long-term relationship. The third strategy involves educating the client on the components of the service. By explaining the depth of preparation and the intellectual property involved, the consultant helps the client move away from the salary divided by hours mindset. If the budget remains a hard barrier, offering a referral to a more junior professional is a high-integrity move. This approach helps a peer get started, provides the client with a solution, and reinforces the consultant's position as a high-level expert with an abundance mindset.

When Emotions Run High, Here’s What to Do - The Upside

Ghosting by potential clients is a common challenge for independent consultants that often carries significant emotional weight. When a prospect stops responding after a discovery call or proposal, it can lead to frustration and wasted mental energy. There are three primary ways to handle this situation. First, consultants can choose to follow up weekly under the assumption that a lack of response is a maybe rather than a no, provided they have the emotional stamina to do so. This persistent approach relies on the belief that the prospect remains interested but is simply occupied. Second, one can assume the best about the prospect, recognizing that personal or professional crises often cause delays. Life events like family emergencies, childcare issues, or company restructuring can easily derail a client's responsiveness. In these cases, moving on and following up in a month to check on their well-being is a more empathetic and less draining path. Third, the Hail Mary email approach involves sending a final message that politely states the consultant will move on and open up their schedule for other clients if they don't hear back by a specific deadline. This tactic helps the consultant regain control of their time and mental space. The suggested template for this email is direct and respectful, noting that the project will no longer be considered a priority if a response isn't received by the end of the day. Ultimately, the goal is to remove the emotional burden of pending responses to focus on more productive tasks. Erin Halper, founder of The Upside, emphasizes that prospects who have never been independent consultants often don't realize the impact of their silence. By taking an emotional temperature and choosing a clear path forward, consultants can avoid the mental drain of ghosting and keep their focus on growth.

Scale Your Time, Scale Your Calendar - The Upside

Managing a calendar effectively is a critical skill for independent consultants because time is their most limited resource. Erin Halper, founder of The Upside, developed these strategies after leading hundreds of consultants who were looking for ways to work less while scaling their impact. There are several proven ways to maximize productivity and scale time. One common method is timeblocking specific tasks like business development, client delivery, and administrative work. This works best for those with high discipline. Another approach involves scheduling unstructured free spaces. These blocks have no agenda and allow for strategic thinking or personal tasks, providing much needed breathing room. Visual organization helps too. Color coding different categories like client meetings or operations gives a bird's-eye view of time distribution. Using emojis at the start of calendar events provides quick visual cues that eliminate the need to read every entry. Scaling also requires looking at what tasks to stop doing. Outsourcing low-value, non-billable work to a virtual assistant is often a consultant's first hire. This includes tasks like invoicing, scheduling, and document formatting. Beyond business tasks, outsourcing personal chores like laundry or meal prep can reclaim significant hours. The goal is to compare the cost of outsourcing against billable rates or the value of personal time. Proactive management prevents burnout and helps build a business that offers true flexibility. Tracking daily activities for a month helps identify exactly where these hours are going. Reclaiming even five hours a week allows for more focus on high-impact growth activities or personal well-being. Being intentional about these choices is the difference between a business that feels like a trap and one that offers genuine autonomy.

Why Caring Too Much Can Be a Bad Thing - The Upside

Independent consultants and entrepreneurs often face a specific hurdle that slows their growth: caring too much. While empathy and dedication are natural traits for advisors and coaches, an excess of emotional investment in clients, outcomes, and minor details acts as a heavy weight during the entrepreneurial journey. Erin Halper, founder of The Upside, observes that the most successful professionals are those who can move on quickly from setbacks, ignore external judgment, and avoid overanalyzing every client interaction. The tendency to agonize over perfection or dwell on negative experiences consumes mental energy that should be directed toward high-level CEO tasks. This emotional clouding often prevents consultants from applying the same clear, unbiased logic to their own businesses that they provide to their clients. By intentionally releasing the need for perfection and the habit of taking business situations personally, entrepreneurs can achieve greater clarity and speed. The core strategy involves identifying thoughts or individuals that occupy unnecessary brainspace and treating them as minor distractions rather than significant obstacles. Shifting focus away from what others think and toward rapid execution, such as posting on LinkedIn even when content feels imperfect, allows for faster business advancement. This shift is particularly difficult for those in advisory roles who are naturally inclined to care deeply about their work and their clients' success. However, when building a consultancy, that same level of care can lead to poor decision-making and a lack of momentum. Ultimately, the goal is not to stop caring entirely but to calibrate emotional investment so it supports rather than hinders business acceleration. Releasing emotional weight allows a founder to feel lighter and move faster, which is often the primary differentiator between those who struggle and those who achieve rapid success in the independent market.

Pricing from a Place of Abundance, Not Fear - The Upside

Consulting pricing is fundamentally a psychological challenge rather than a mathematical one. While tools and worksheets can inform a rate, the ability to command high fees stems from a mindset of abundance rather than scarcity. If a consultant does not believe their work is worth a premium, clients will sense that hesitation and lose confidence in the engagement. Fear often drives pricing decisions, manifesting as imposter syndrome, the dread of being laughed at, or the worry that a high quote will kill a deal. These scarcity-driven thoughts, such as the fear of having to return to a full-time job or scaring off every potential lead, actually undermine the business's long-term health. Shifting to an abundance mindset changes the consultant's market positioning. High pricing functions like a luxury brand by signaling quality and attracting high-ticket clients who value results over cost. Paradoxically, high rates build trust. When a consultant prices their services appropriately for the value delivered, it reassures the client that the consultant is confident in their ability to solve the problem. Conversely, underpricing can make a client nervous, leading them to wonder if the consultant truly understands the scope or has the necessary expertise. The impact of pricing extends to the quality of the client base. Low-paying clients tend to be more difficult and refer other low-budget prospects, whereas high-paying clients breed a network of similar high-value opportunities. From a business operations perspective, raising rates by even 25% can transform a consultant's lifestyle, either by significantly increasing annual revenue or by allowing them to maintain their current income while working fewer days per week. This financial padding provides security during lulls and ensures the business remains healthy. It is always easier to scale down a scope if a price is too high than it is to raise rates once a low baseline has been established.

I Didn’t Expect To Become an Expert in This. - The Upside

Erin Halper, founder of The Upside, reflects on her unexpected evolution from an independent consulting expert to a recognized authority in community building. Launched in 2018, The Upside pioneered a virtual, monetized community model where the community itself was the primary product rather than an add-on to a course or coaching program. While the model was initially met with skepticism, the COVID-19 pandemic accelerated the demand for virtual, sustainable business structures, leading to a surge in competition. Despite this, The Upside has maintained its market position and was recently ranked in the top 10% of over 10,000 communities on the Circle platform. The core of Halper's strategy is a radical focus on member retention rather than acquisition. She spends 99% of her resources on serving existing members, which results in low turnover and high referral rates. Marketing is minimal, consisting primarily of a weekly newsletter and quarterly virtual open houses. This approach challenges the traditional focus on constant lead generation and highlights the value of nurturing existing client relationships as the most effective growth engine. Halper encourages other professionals to lean into the expertise others see in them, even if it differs from their original focus, and to prioritize their current client base as their strongest source of new business.

Here’s How to Dream Bigger in the New Year - The Upside

Erin Halper, the founder of The Upside, challenges professionals to move beyond conventional goal setting by identifying objectives that feel genuinely frightening. This philosophy, rooted in advice from success coach Christina Langdon, suggests that the most impactful goals are those that provoke a sense of discomfort or even absurdity. When a goal feels too big, it often triggers a defensive response because it forces an individual to acknowledge personal baggage and the possibility of public failure. The resistance to dreaming big usually stems from several specific psychological hurdles. These include the fear of setting oneself up for disappointment, the feeling that a goal is overly privileged, or the sense that the ambition is simply ridiculous. Halper explains that these feelings are actually indicators of where the most significant growth can occur. For many independent consultants, a truly ambitious goal might even question their entire professional identity, making it easier to ignore the dream than to face the discomfort of pursuing it. The recommended approach for 2025 is to lean into this discomfort rather than shutting down. Instead of dismissing a goal that feels out of reach, Halper suggests writing it down and keeping it in a safe place. This simple act of acknowledgement shifts the mindset from avoidance to exploration. By documenting the scary goal, you create a baseline for future growth and give yourself permission to investigate what it would take to actually achieve it. For the community at The Upside, which focuses on independent consulting and career autonomy, this type of goal setting is essential for transitioning from corporate structures to a more purposeful professional life. The process is less about immediate achievement and more about the willingness to push through the mental barriers that keep professionals playing small.

Here’s How to Win by Being More Human - The Upside

Business is fundamentally about human relationships, not just corporate entities or legal contracts. For independent consultants, this human connection is a primary competitive advantage over larger agencies. The case study of Jessica illustrates this. She had a two-month strategy project where the client ran out of funds halfway through. Legally, her contract entitled her to the full fee. However, instead of aggressively pursuing the remaining $5,000, which likely would have yielded nothing and burned the bridge, she chose to meet the client for coffee to understand their situation. By treating the client as a person rather than a company, she discovered they were facing significant personal and business crises. This empathy led to a creative solution: the client referred her to a high-profile business podcast. The resulting exposure from the podcast appearance, combined with Jessica's proactive promotion of the episode, led to two new project inquiries totaling $80,000. Both deals closed. The core takeaway is that preserving a relationship often yields far greater financial and professional returns than winning a legal battle. In difficult situations, consultants face a choice between the fight or the relationship. Choosing the latter builds trust and opens doors to future opportunities that a rigid, contract-first approach would close.

Here’s What Not to Do on LinkedIn - The Upside

LinkedIn success depends on prioritizing quality over quantity. Many users make the mistake of messaging strangers or loose connections to pitch services before establishing any rapport. This transactional approach often backfires, leading recipients to delete messages and remove connections because they feel like a line item rather than a human being. Researching a prospect for even thirty seconds can prevent embarrassing outreach that ignores the recipient's existing resources or expertise. A more effective strategy involves a patient, relationship-first methodology. This includes engaging meaningfully with a prospect's posts for at least a month to show genuine investment in their thought leadership. Beyond just liking posts, commenting on their existing comments can spark real conversations and build a sense of community. Deep research is also essential. Learning about a person's hobbies, charitable interests, or listening to their recent podcast interviews provides the necessary context to open doors authentically. When the time comes to reach out, the proposal must offer a clear, specific benefit for both parties. Vague offers to support one another are often ignored. Instead, highlighting shared audiences or suggesting specific collaborations, like newsletter features, creates a compelling win-win scenario. Selling should only occur when there is a visible, specific need that the sender can solve. Ultimately, building a healthy business requires patience and a focus on long-term relationships rather than immediate transactions.

Episode 193: Unlocking the Power of Community: How to Thrive as an Independent Consultant with Erin Halper - Jessica Fearnley

Independent consulting often begins with a desire for autonomy, but the transition from a structured corporate environment frequently leads to isolation and burnout. Erin Halper, founder of The Upside, explains that while the initial urge to work alone is common, long-term sustainability depends on finding a support network that fulfills the human need for belonging. When professionals leave corporate roles, they lose more than just a paycheck. They lose the built-in infrastructure of marketing, accounting, and operations departments. As a solo consultant, you suddenly inherit all these roles, which can quickly lead to overwhelm. The Upside was created to bridge this gap, providing a community of over 250 consultants who share resources and support. A critical part of this journey is shedding the corporate armor. High achievers are often trained to hide weaknesses and present a perfectly polished image, but this mask can be a barrier to building the authentic relationships required for a successful independent practice. Authenticity is described as the winning game in consulting because it allows for deeper connections and more transformative opportunities. When evaluating potential communities, consultants should prioritize value alignment over flashy marketing or celebrity endorsements. A significant red flag is a community that cannot clearly articulate its values or what it stands for. The right network should inspire its members and make them feel seen and understood. Active participation is also essential. The value of a community is directly tied to how much a member engages and shows up as their true self. Ultimately, the goal is to move from a performance-based corporate mindset to one of genuine connection and mutual support.

Trend Report and Action Steps for 2025 - The Upside

2024 was marked by significant client indecision and delayed project starts, a trend that persists into 2025. Independent consultants and advisors are seeing prospects request services but hesitate on final commitments because of economic uncertainty and job security concerns. This environment makes persistent follow-up essential. Successful consultants are those who maintain contact through helpful resources and check-ins, operating under the mindset that a lead is a potential yes until they receive an explicit no. Differentiation has moved from a luxury to a necessity. In a crowded market where clients often default to doing nothing, consultants must establish clear thought leadership and personal trust to stand out. Speed to lead is a critical competitive advantage. Data from the community suggests that turning around a proposal within 48 hours of a discovery call significantly increases win rates. Delays of even a week often result in losing the project to more responsive competitors. Finally, the most effective lead generation strategy for 2025 is mining existing networks. Cold outreach is increasingly ignored because of high volume. Instead, returning to former colleagues, past employers, and old leads provides a higher ROI. Building a system for proposal management and relationship maintenance is the primary path to stability in the current consulting landscape.

Here’s What You Can Learn from the Giannis Effect - The Upside

Giannis Antetokounmpo's life story, as detailed in a recent documentary, provides a framework for professional growth and business leadership. The Giannis Effect is built on three foundational values: the management of fear, the reframing of failure, and the prioritization of loyalty. Giannis's journey from an immigrant in Greece to a two-time NBA MVP and champion highlights the importance of handling fear effectively. He suggests that the primary difference between a hero and a coward is their response to fear. For business owners, this means acknowledging and leaning into the anxieties of entrepreneurship rather than letting them dictate actions. The second pillar focuses on the inevitability of failure. Giannis argues that failures are merely stepping stones to success. In a business environment where setbacks occur daily, spending time on self-criticism or wallowing in mistakes is counterproductive. Instead, entrepreneurs should view these moments as necessary components of the path to the top. The faster a leader can learn from a failure and move on, the quicker they reach their objectives. The final value is the belief that loyalty trumps riches. Giannis famously stayed with the Milwaukee Bucks despite offers of higher pay and more prestigious locations. His reasoning was rooted in the fact that the Bucks were the first to believe in him, helping his family secure visas and providing essential mentorship. In the context of independent consulting and business, this suggests that financial implications should not be the sole driver of decisions. Choosing loyalty to those who supported your growth often leads to more fulfilling and sustainable outcomes. Erin Halper, founder of The Upside, uses these lessons to encourage independent professionals to transition from corporate life with a renewed sense of purpose and autonomy.

Working on the Business Vs. In the Business How to Create the Perfect Balance - The Upside

Transitioning from a freelancer to a business owner requires a fundamental shift in how time is allocated. Many consultants fall into the trap of spending all 40 hours a week on client deliverables. While this keeps the lights on, it neglects critical growth levers like thought leadership, strategic thinking, and relationship building. To build a predictable pipeline and achieve financial freedom, you must carve out time to work on the business rather than just in it. This shift is essentially moving from a freelancer execution model to a CEO mindset. Relying solely on referrals is a risky long term strategy because they eventually dry up. Success isn't about a specific magic number of hours but rather creating a consistent system you can stick to. Specific activities that define working on the business include community engagement, LinkedIn presence, and creative thinking. These are often the first things to be sacrificed when client work gets busy, but they are the foundation of a sustainable practice. To maintain this balance, you need a system that removes client distractions. This might involve strict calendar blocking where you refuse to cheat on your own time. Other effective tactics include changing your physical location to spark creative thinking or co-working live on Zoom with a peer for accountability. Surrounding yourself with people who are a few steps ahead of you or joining a coaching group can provide the necessary perspective to grow with intention. Ultimately, even 30 minutes a week of high level strategic zooming out can prevent the feast or famine cycle common in independent consulting. By treating your own business as a primary client, you ensure that you are building an asset that can eventually scale without requiring more of your personal time.

Put the Blinders on, Change Your Mindset Forever - The Upside

Comparing your business to competitors based on LinkedIn posts or lifestyle cues is a trap that many independent professionals fall into. Many consultants assume a competitor is successful because of external markers like a nice apartment or a large social media following. However, these markers often hide the reality of their situation. You cannot see their actual salary, client count, stress levels, or the source of their funding. They might have an inheritance or a wealthy spouse rather than a profitable business. This curated online presence creates an unrealistic benchmark that distracts from your own progress. Instead of tracking others, the focus should remain on internal growth. This means staying nimble and trusting your own instincts. It involves building unique intellectual property and developing your own thought leadership. Embracing failures and learning from them quickly is more valuable than worrying about what a competitor is doing. The goal is to ignore the noise and surround yourself with smart people who help you move forward. Putting the blinders on allows you to make better decisions without the weight of false comparisons. Erin Halper, founder of The Upside, argues that this mindset shift is essential for independent consultants who want to achieve true autonomy and purpose. By focusing on what is straight ahead, you protect your mental energy and build a business based on your own values rather than someone else's highlight reel. This approach prevents you from making assumptions about who knows more or who is worth emulating, ensuring your strategy remains authentic to your specific goals.

5 Ways to Create Equitable Offerings, While Still Making Money - The Upside

Balancing the desire to help people with the need to hit revenue goals is a major challenge for independent consultants. Many people think they have to work harder or take on more clients to make up for lower fees, but that usually leads to burnout. The better approach is the oxygen mask principle: you have to fix your own financial health and schedule before you can help anyone else. If your business isn't stable, you won't have the bandwidth to support anyone in the long run. There are five practical ways to stay equitable without losing money. First, give away high-value resources. Tools like a Pricing Playbook or a lead gen guide help people who aren't ready for a full engagement yet. This builds your reputation and provides a path for them to follow until they can afford your services. Second, host free group events. Quarterly Zoom calls or office hours let people tap into your braintrust without you having to book 1:1 time for every request. It turns a high-touch service into a one-to-many interaction. Third, consider a 1:1 podcast. Coaching someone live on a show provides free value to them while acting as a massive "show, don't tell" marketing asset for your business. It showcases your expertise to a much larger audience than a private call ever could. Fourth, use a scholarship model. Instead of lowering your rates across the board, set aside a specific number of spots for preferred pricing. This requires clear rules on who qualifies and what they get so it doesn't eat into your main revenue or create confusion about your market value. Finally, just volunteer. Separating your business from your charity work by joining a mentorship program lets you give back without messing with your professional fee structure. These methods ensure you can be generous while still building a profitable, sustainable business that lasts.

Here’s How to Set Yourself Apart - The Upside

Consulting services are frequently viewed as commodities by potential clients, making the individual consultant the primary differentiator. While technical skills and knowledge are necessary, they are often seen as baseline requirements that many competitors also possess. To stand out, consultants must move away from the corporate mindset that work should speak for itself. Instead, success in the independent market relies on building human connections. Founders and companies hire people they like, trust, and feel a connection with. This requires consultants to be authentically human by sharing their vision, personal passions, and career stories. By revealing what drives them beyond their professional tasks, consultants can build the rapport necessary to secure high-level engagements. Erin Halper emphasizes that for every hiring decision, there is a human making that choice based on more than just a resume or a list of deliverables.

210. The Upside of Community: How Erin Halper Empowers Independent Consultants

Erin Halper, founder of The Upside, shares her journey from corporate employee to leader of a global community for independent consultants. After a health crisis made corporate flexibility a necessity, she noticed a growing trend of women leaving traditional roles without realizing consulting was a viable path. Her initial business model focused on consultant matchmaking, but she eventually pivoted after realizing that consultants struggled more with positioning and business building than just finding leads. This shift led to the creation of a true community rather than a transactional network. A core pillar of her approach is the strict no-selling boundary within the community, which fosters a high-integrity environment where members focus on support and collaboration. Halper emphasizes the importance of personal branding, noting that solo practitioners must stop hiding behind a business name and embrace being the face of their brand. The community's growth is driven by a flywheel effect and a unique referral model where members are rewarded with 1:1 time with the founder. By dismantling the competition myth, Halper demonstrates how transparency and generosity among peers can create unstoppable momentum for everyone involved. The discussion also covers the maturity required to handle member churn and the necessity of serving only true business owners who value their expertise.

Would You Do It for Double the Pay? - The Upside

When a consulting project starts feeling like a burden, the root cause is often a mismatch between the effort required and the compensation received. A common mistake among independent professionals is assuming a client or service line is no longer viable when, in reality, it is simply underpriced. Erin Halper highlights this through a conversation with a visible consultant who felt a $3,000 monthly retainer was no longer worth the time. The pivot point occurs when asking if the work would be worth doing for $6,000 instead. If the answer is yes, the issue isn't the client or the tasks, but the financial return. Consultants often hesitate to raise rates because they assume the market won't support higher fees. However, if a consultant is already prepared to drop a client or stop offering a service, they have reached a 'nothing to lose' state. This provides the perfect leverage to test significantly higher pricing. Even if existing clients reject the new rate, the higher fee should be the baseline for all new inbound inquiries. This strategy allows consultants to find the ceiling of what the market will pay without risking their current stability. The goal of this pricing shift is to move from a state of resentment to one of 'only upside.' When the pay matches the energy required, the consultant can show up fully without feeling drained by the opportunity cost of their time. This methodology is central to the philosophy of The Upside, which focuses on helping corporate professionals transition into high-value independent consulting roles. By picking a number that makes the work genuinely worth the effort, consultants maintain their autonomy and professional purpose while maximizing their revenue potential.

Here’s How Gambling Could Pay Off - The Upside

Erin Halper uses a trip to Las Vegas to reflect on the psychology of risk and how it applies to independent consultants and entrepreneurs. She identifies a common struggle where people find it difficult to handle both winning and losing. For some, a small win feels insufficient to stop, while a small loss triggers a desperate need to break even. This low risk tolerance often prevents business owners from thinking bigger or taking bold actions. Halper outlines three core principles to overcome these mental hurdles. First, every win counts regardless of size. Whether it is a guest spot on a minor podcast or a $5,000 project, these moments build visibility and authority. Even closing a client at a price that feels too low is a win because it provides a lesson for future pricing strategies. Second, entrepreneurs should focus on net gain rather than tallying incremental losses. Instead of obsessing over lost opportunities or low engagement, zooming out to look at progress over a full year provides a more accurate picture of success. Loss is an inherent part of business, and maintaining a net positive trajectory is the goal. Finally, she emphasizes that success requires active participation. Just as a gambler must place a bet to win at blackjack, an entrepreneur must be willing to bet on themselves. There are no passive wins in consulting. Taking chances and moving through discomfort are necessary drivers for progress. The piece encourages readers to view their wins with clarity and to take bold steps that might feel slightly uncomfortable but lead to significant growth.

Consistent Engagement on LinkedIn Pays Off - The Upside

Jill Kravetz, a strategic advisor, secured a feature in the Boston Globe by maintaining a consistent habit of engaging with a reporter's LinkedIn posts. This reporter, whom she knew loosely for two decades, had not contacted her for a comment since 2015. The breakthrough happened because Jill made a weekly habit of commenting on posts from old connections, podcasters, and journalists. This visibility led to her being cited as an expert in an article about Kim Kardashian's private equity firm. The core philosophy presented is that LinkedIn success requires a long-term strategy rather than a transactional mindset. Many consultants fail by treating the platform as a lead-gen tool for instant wins or by obsessing over engagement metrics. Instead, the focus should be on visibility and building genuine relationships. Commenting is highlighted as a critical, often overlooked tactic because creators always read the comments on their own posts. This makes it an effective way to get on the radar of reporters, potential clients, or podcast hosts. Another common mistake is posting exclusively about work. To move from a commoditized consultant to a trusted thought leader, professionals must share personal stories and visions that reveal the human behind the business. Finally, the approach of connecting and immediately DMing services is discouraged. Success comes from nurturing relationships over time, which naturally leads to growth and authority in a specific niche like private equity or strategic advisory.

An A+ Won’t Make You a Successful Entrepreneur - The Upside

High achievers often find that the traits making them successful in school or corporate roles do not translate well to entrepreneurship. Erin Halper, founder of The Upside, notes that many Ivy League graduates and top performers struggle when building their own businesses because they are used to a world with clear rules and external validation. In corporate environments, there are no grades for pitch decks or extra credit for long hours. The rigid A+ student path also fails to account for life's unpredictable turns like family changes, health issues, or the desire for a complete career pivot. Entrepreneurship demands a different toolkit: resilience, quick decision making, and a high tolerance for discomfort. Interestingly, many successful founders were average students who struggled in traditional academic settings. To succeed as an independent consultant or founder, high achievers must unlearn their old habits. This involves prioritizing resilience over just deepening expertise. It means choosing progress over perfection to scale faster and defining success by personal values rather than external benchmarks or ego. The transition requires a shift from avoiding failure to using it as a necessary stepping stone. Halper suggests that instead of sharpening expertise, professionals should focus on their ability to bounce back from setbacks. Working smarter means moving away from polishing every detail and focusing on what drives the business forward. Ultimately, the goal is to build momentum without the fear of judgment or the need for a perfect score. This approach allows for more flexibility and a renewed sense of purpose that the corporate ladder often fails to provide. The Upside community serves as a space for these recovering A+ students to support each other through the messy process of building a business based on their expertise.

Futureproof Your Consultancy - The Upside

The consulting landscape in 2025 requires a shift from seasonal reactions to long term strategic planning. Futureproofing is defined as a mix of offense and defense: protecting your business foundation while identifying growth opportunities during uncertainty. Current market conditions show a significant shift in buying culture. After years of high spending, clients are experiencing fatigue and economic anxiety, leading to a pullback in traditional large scale engagements. This has created a demand for accessible offerings, which are quicker, lower friction services that provide immediate value without requiring massive upfront investments. Clients now operate with a downsizing mentality, becoming more selective and skeptical of outside expertise. They are not stopping their use of consultants but are demanding higher quality and clearer proof of value. To thrive, consultants must move beyond reacting to the market and instead anticipate client needs. Disruption is framed as an opportunity for reinvention rather than a threat. Successful firms are avoiding the trap of chasing every micro trend. Instead, they focus on carving out clear, ownable thought leadership and specific positioning. The current environment is described as uniquely volatile, comparable to 2020, where some consultants see record growth while others struggle. Navigating this requires being nimble and resilient. Key actions for evolution include reimagining the business model, rethinking target spaces, and redesigning service offerings. Ultimately, the consultancies best positioned for the future are those that prioritize strategic value and clear differentiation over generic service delivery. This approach allows consultants to maintain relevance even as client budgets tighten and procurement processes become more rigorous. By focusing on the why behind their business and rebuilding networks around high value outcomes, consultants can transition from being seen as a luxury expense to an essential strategic partner. This evolution involves a willingness to rip up old models and start over if the current positioning no longer aligns with the skeptical, value driven mindset of modern buyers.

How Do You Know If You’re Ready to Scale? - The Upside

Scaling an independent consulting practice requires a fundamental shift from high-touch, time-intensive activities to systems that produce more output with less personal time. A common bottleneck for consultants is the hamster wheel of discovery calls, daily operations, and client delivery, which leaves little room for strategic growth. Erin Halper illustrates this transition through her own experience with The Upside, where she replaced approximately twenty 30-minute 1:1 discovery calls per month with a single 90-minute quarterly Open House event. This shift not only reclaimed significant time but also enhanced the value for prospective members by providing a community vibe and peer perspectives that 1:1 calls could not replicate. The primary indicator of readiness to scale is the willingness to intentionally carve out time to work on the business rather than just in it. Many consultants struggle with guilt when not performing billable work, viewing strategic thinking as unproductive or a waste of time. However, scaling is a proactive choice rather than a passive occurrence. Successful scaling often involves external structures such as coaching programs, dedicated calendar blocks, accountability partners, or professional communities like The Upside. Without a deliberate decision to step back from the busy work of daily tasks, consultants remain trapped in the weeds, unable to build the pathways necessary for sustainable expansion. The transition to a scale-ready mindset involves recognizing repetitive patterns, such as answering the same questions repeatedly, and designing more efficient, one-to-many solutions to address them. This intentionality is the core differentiator between a consultant who is simply busy and one who is building a scalable enterprise. By moving away from the constant cycle of delivery and discovery, a consultant can finally focus on the high-level architecture of their practice.

20/20 Market Research: Understand Your Clients While Building Relationships - The Upside

The 20/20 Market Research framework is a structured approach for independent consultants to gather market insights while simultaneously building rapport with potential clients. The method involves a 40 minute call split into two equal segments: 20 minutes for the consultant to ask research questions and 20 minutes for the prospect to receive expert advice. This reciprocal model creates a win-win scenario where the consultant gains valuable data and showcases their expertise, while the prospect receives immediate value. The framework is particularly effective for refining service offerings, improving messaging, and understanding how a brand is perceived in the market. Key questions focus on identifying client goals, such as what keeps them up at night or what they would change with a magic wand. It also includes perception checks to see how prospects describe the consultant's work to others. A case study of The Upside community demonstrates the framework's practical application. Through these calls, the founder discovered three primary barriers to joining: prospects felt their business wasn't ready, they weren't fully committed to their venture, or they were already in general networking groups. These insights led to specific GTM pivots, including updating homepage messaging to emphasize that the community meets consultants where they are and refining the referral process to target 'all-in' entrepreneurs. The framework also highlights the need to differentiate between immediate networking and long-term financial ROI when positioning a professional community.

They’re Buying You above All Else - The Upside

Trust acts as the ultimate shortcut in the sales process, particularly for independent consultants and fractional leaders. When a potential client or collaborator has deep-seated trust in an individual, they are often willing to commit to an offering without knowing the specific deliverables, price, or location. This happens because the buyer is investing in the person and the anticipated experience rather than a specific product or service. Most cold or semi-warm outreach fails because it lacks this foundation, leading to skepticism about time, money, and effort. Common pitfalls include unclear intentions, high price tags, or aggressive sales tactics that trigger a lack of trust response. In contrast, successful outreach leverages existing relationships where values are already aligned. Erin Halper illustrates this through a personal anecdote where she paid for a private event within five minutes of receiving an invite, despite not knowing the agenda or location, simply because she trusted the host's expertise and values. Building this level of trust requires consistent visibility and authenticity. By writing in a personal voice and sharing a clear vision, consultants attract clients who resonate with their specific approach. Relationships serve as the most valuable currency in this market. To maximize results, professionals should focus on nurturing their existing network, customizing their outreach, and maintaining a persistent follow-up strategy. The goal is to become the person that others want to be a part of, regardless of the specific project or event. This approach turns the sales motion from a hard sell into a natural extension of a trusted relationship. It shows that those who already trust you are your biggest advocates and warmest leads. By putting yourself out there and embracing imperfections, you attract the people who will say yes, simply because of the person behind the work. This methodology fits perfectly into the Consultant OS workflow, where the individual's brand and network are the primary drivers of sustainable business growth.

A Lesson on Boundaries from an Unexpected Source - The Upside

Erin Halper uses Chick-fil-A's strict policy of being closed on Sundays as a case study for maintaining business boundaries, especially during economic uncertainty. When business owners face a scarcity mindset, they often compromise on their values or availability to please clients. However, the success of Chick-fil-A proves that standing firm on boundaries does not preclude growth. The core message is that consultants teach clients how to treat them. Just as children or pets thrive with structure, clients respect professionals who communicate and enforce clear rules. The text provides a practical framework for consultants to define their availability, responsiveness, and financial terms. This includes setting specific working hours and defining response times for emails. It also suggests establishing after-hours surcharges for emergencies to ensure that extra time is compensated fairly. Crucially, it advocates for a strict policy where all deliverables and meetings are immediately paused if a payment is late. By incorporating these terms into contracts and daily operations, independent consultants can avoid burnout and maintain professional authority. The author emphasizes that boundaries should be communicated clearly and stuck to regardless of the current economic climate. This approach helps shift the consultant-client relationship from one of reactive service to one of mutual respect and professional partnership. The provided worksheet serves as a template for defining these parameters, covering everything from meeting pre-approvals to the withholding of work products when invoices are overdue. Ultimately, the goal is to move away from the fear-based decisions that often arise during market volatility and instead lean into the structures that allow a consulting practice to scale sustainably.

Learnings from a Rude Client Pitch - The Upside

Erin Halper shares a pivotal failure from the early days of The Upside when it operated as a boutique matching firm for consultants. The core of the failure was a discovery meeting at a tech company that went south due to three specific preparation mistakes. First, there was no clarity on who the actual meeting participants would be. Second, the internal champion who secured the meeting was not present to advocate for the firm. Third, that champion had not been equipped with the right language to properly frame the firm's value to the rest of the team. This resulted in a meeting with an HR director who viewed the session as a waste of time and treated it as a transactional pitch rather than a strategic conversation. During the encounter, the HR director compared the boutique firm to Robert Half, a large staffing agency. Halper initially reacted by becoming defensive and justifying her company's edge, which she later identified as a mistake that gave the prospect 'gotcha' satisfaction. The experience led to several tactical shifts for her consulting practice. She now emphasizes that first meetings must be for building relationships, not selling. She advises consultants to stay in the driver's seat by asking questions and listening rather than being grilled. If a prospect makes a dismissive or rude comment, the best response is to breathe and redirect with a curiosity-based question like 'What made you think that?' to uncover the prospect's underlying assumptions. This approach allows the consultant to regain control of the narrative and gather valuable feedback for future sessions.

10 Ways to Stop Client Ghosting - The Upside

Ghosting is a frequent hurdle for independent consultants that usually signals a breakdown in the sales process or a lack of qualification. To reduce ghosting, consultants must prioritize pre-qualifying leads based on fit, budget, and urgency. Engaging directly with decision-makers is essential, as junior champions often fail to convey value effectively. During discovery, it is vital to protect intellectual property by defining the problem without giving away the solution for free. This approach maintains the consultant's perceived value and prevents clients from attempting a DIY fix. Effective discovery involves asking questions that help the client quantify the cost of their problem. By aligning the work with one of the Four Pillars of Value—revenue growth, cost reduction, access, or solving a growth headache—the consultant shifts the conversation from a service to a business investment. Instead of trying to be interesting, the goal is to be interested, using questions like "What do you hope to achieve?" and "How much do you stand to lose if you do nothing?" to uncover the true stakes. Operational changes also play a role. Discussing pricing ranges early prevents sticker shock, while reviewing proposals live during a meeting allows for immediate feedback and objection handling. Adding expiration dates to proposals creates a professional boundary and a natural reason to follow up. If a lead remains silent after multiple attempts, a final Hail Mary email can be used to professionally close the file and free up capacity for other clients. This email should be lighthearted but firm, suggesting that if no response is received, the project is no longer a priority and the held space will be opened for others. Ultimately, managing the sales process with these boundaries respects the consultant's time as a scarce resource and positions them as a high-value partner rather than a desperate vendor.

Consulting 101: Real talk on pricing, positioning, and staying sane while building your own thing

How I Landed a Hello Monday Podcast Feature - The Upside

Erin Halper, founder of The Upside, explains how she secured a guest spot on Jessi Hempel's Hello Monday podcast through organic LinkedIn engagement rather than a direct pitch. The process started when a contact tagged her in a post about consulting. Halper contributed her own perspective, which prompted her community to join the conversation. This collective engagement signaled her expertise to the host. After three weeks of silence where Halper intentionally avoided following up, Hempel reached out to invite her to the LinkedIn studio. The success of this interaction relied on years of foundational work, including consistent newsletter writing, public speaking, and maintaining a strong LinkedIn presence. Halper argues that being positioned as an expert through long-term content creation makes the eventual 'sell' unnecessary because the value is already visible. She advises professionals to start sharing their points of view immediately and to keep their LinkedIn profiles optimized for when these opportunities surface.

How to Make the Most out of Visibility Opportunities - The Upside

Erin Halper provides a detailed roadmap for independent consultants to maximize the impact of media features. She uses her recent appearance on Jessi Hempel's Hello Monday podcast as a primary case study. The central argument is that landing a major feature is not a finish line but a starting point for a broader marketing campaign. Simply waiting for opportunities to arrive after a feature is published is a losing strategy. Instead, consultants must actively run with the momentum to ensure the visibility translates into tangible business growth. The framework begins with LinkedIn optimization. Halper recommends updating the profile banner image to include media logos and specific screenshots from the appearance. This provides immediate visual social proof to anyone visiting the profile. She also emphasizes the importance of content distribution. Rather than a single "I am thrilled to be featured" post, she suggests creating at least three distinct posts. These should use different storytelling angles to keep the audience engaged. Engaging with every comment on these posts is critical for building community and keeping the conversation alive. High performing posts should then be pinned to the Featured section of the profile for long term visibility. Beyond social media, the strategy involves deep integration into digital assets. This includes adding press logos to the website homepage, creating features on "Our Story" pages, and listing the appearance in resource or wisdom sections. Halper also highlights the power of direct communication. Adding a link to the feature in an email signature builds passive credibility with every message sent. More importantly, the feature serves as a perfect anchor for strategic outreach. It gives consultants a non-salesy reason to reach out to past colleagues, clients, or partners to stay top of mind. The document also explores the mindset shifts needed for 2025. It notes that showing up as a polished corporate figure can actually be a disadvantage. Authenticity and vulnerability are often more effective for building the trust required in independent consulting.

"Why and When" to Raise Your Prices - The Upside

Raising prices is often a psychological hurdle for consultants, even when backed by clear ROI and significant reinvestment. Higher pricing often acts as a signal of quality, much like luxury brands, where a higher price point increases client confidence in the value delivered. Conversely, pricing that is too low can cause potential clients to lose faith in a consultant's ability to provide the desired return on investment. For many, the goal should be fewer high-value engagements rather than a high volume of low-priced projects, as the latter requires significantly more administrative overhead and energy. A price increase can also serve as a forcing function to level up business operations, such as sharpening discovery calls, improving onboarding, or hiring support staff. Trust is the primary driver of price elasticity. By quantifying the cost of a client's problem and the potential gains of a solution during the discovery phase, consultants can position themselves as business-critical partners. If proposals are consistently met with immediate acceptance, it is a strong indicator that the current rates are below market value. Effective pricing should reflect the value and results delivered rather than just the time spent.

"How" to Raise Your Prices - The Upside

Raising prices for existing clients is often a source of anxiety for consultants, but it becomes manageable when you are willing to part ways with those who cannot meet your new rates. The process starts with early communication, ideally providing at least two months of notice to allow clients to adjust their budgets. For commoditized services like legal or accounting work, a standardized, impersonal annual email is an effective way to announce increases without opening the door for negotiation. In contrast, non-commoditized or high-value consulting requires a more personal touch. This involves a verbal conversation with the decision-maker followed by a written summary to demonstrate professionalism and confidence. It is also beneficial to notify past clients of rate changes via email. This prevents sticker shock if they return and serves as a way to stay top of mind while signaling business growth. When explaining the increase, honesty is key. Reasons can include rising expenses, a shift toward higher value delivery, or a business model change that involves taking on fewer clients. Ultimately, the consultant maintains the power to decide whether to compromise or move on if a client pushes back.

Should You Use AI to Write Your Content - The Upside

Erin Halper, the founder of The Upside, addresses the growing pressure to use AI for content creation and explains why she refuses to use tools like ChatGPT for her weekly Wednesday Wisdom emails. Even though she understands that AI could easily repurpose her past podcast interviews and articles to save time, she believes the technology produces a version of her that is too closed-up and perfectionist. She views AI-generated content as feeling somewhat cheap because it lacks the ability to pull from deep, personal memories or describe human feelings in a truly personalized way. For instance, AI cannot suddenly recall a specific story from twenty years ago to illustrate a point or teach a lesson. A major part of her argument centers on the value of the struggle involved in writing. By not leaning on AI, she forces herself to become a better writer, thinker, and creator. This manual process challenges her to dig deeper into her own experiences, pay closer attention to her readers, and sharpen her professional skills. She even points out that imperfect grammar can be a benefit, as it lets the reader know there is a real human behind the keyboard. She notes that while AI is undeniably useful in many contexts, there is no requirement to use it for everything, especially when it comes to personal thought leadership. The piece concludes by inviting readers to join The Upside's community, which prioritizes human connection over automated interactions. She highlights their Give/Get culture of mutual support, where independent consultants can find a personal board of directors and a network of true peers to help break through business plateaus. Her core message is that showing up as your full, authentic self is a strategy that never goes wrong. The emphasis remains on the No AI. All human approach to building a professional brand and community, ensuring that expert advice comes from a unique, human lens rather than an algorithm.

Our Origin Stories Are Powerful Opportunities for Connection - The Upside

Erin Halper details the deeply personal events that led to the creation of The Upside, a community for independent consultants. The journey began when she started her own consultancy to gain control over her schedule, a move that became vital when she faced a high-risk pregnancy. During a routine 20-week ultrasound, doctors discovered a serious heart condition in her unborn son. This news triggered a period of intense medical uncertainty, including two open-heart surgeries before her son turned two. Throughout this crisis, Halper found that her consulting clients provided a stable foundation and the necessary flexibility to prioritize her family. A defining moment occurred while she walked through a pediatric cardiology unit and saw many children alone because their parents lacked the workplace flexibility to stay with them. This observation stayed with her for years as she continued to grow her business, move cities, and handle personal losses. By 2017, Halper realized that many other professionals were seeking the same autonomy she had built but did not know how to start. After countless informal meetings sharing her methods, she identified a significant gap in the market for a structured way to help people launch and scale flexible, consultancy-style businesses. She eventually closed her own firm to focus entirely on building The Upside. The narrative underscores that origin stories are essential for leaders to connect with their audience and build mission-driven organizations. Halper now uses her platform to mentor thousands of professionals transitioning from corporate life into the independent market, emphasizing purpose and autonomy.

Applying Friction to Your Sales Process Can Be a Good Thing - The Upside

Adding friction to a sales process is often seen as a mistake, but it serves as a powerful filter for high-quality, low-volume pipelines. By making the initial steps more demanding, businesses can weed out leads that aren't serious, which protects time and improves the overall close rate. This approach is common in luxury markets, such as high-end real estate or fine art, where pre-qualification is mandatory before any significant interaction occurs. For independent consultants or service providers, friction can take the form of detailed intake applications, self-assessments, or audits. These tools should ask specific questions about the prospect's goals, budget ranges, and urgency. For example, asking if a client is ready to invest $10,000 or $20,000 immediately clarifies whether their expectations align with the service's value. While some potential leads might abandon a long application, the ones who finish are typically more committed and better suited for the work. To prevent turning away the right people too early, a counterbalance is necessary. This involves offering a low-friction way to experience the service, such as a low-cost introductory session or an open house. This taste allows curious prospects to build trust before they commit to the more rigorous application process required for full engagement.

The Importance of Having an Onboarding Process - The Upside

First impressions often dictate the long-term success of a business relationship, yet many consultants focus too heavily on the sales process and neglect what happens after a client says yes. The moments immediately following a signed contract are when a client is most vulnerable to buyer's remorse, asking themselves if they made the right choice or if the provider will actually deliver. A structured onboarding process serves as a professional anchor that relieves these doubts and demonstrates leadership from the start. By taking charge of the narrative early, consultants can turn a single transaction into a cycle of repeat business and high-quality referrals. The Upside community, led by Erin Halper, provides a blueprint for this high-touch approach. Their model includes immediate confirmation emails with specific dates, personalized welcome messages, and a calendar invite to a New Member Meetup. This white-glove treatment is designed to exceed high expectations and integrate new members into the community quickly. Key elements of their strategy involve facilitating 5 to 6 peer connections in the first week, providing curated email introductions, and offering a printable guide for the first three months. They also provide practical tools like LinkedIn announcement templates and intro scripts to reduce the client's cognitive load. This level of hand-holding ensures that members feel comfortable and see immediate results without feeling overwhelmed. Ultimately, a successful onboarding motion is about creating a give and get culture where the consultant guides the client through every step of the journey, ensuring they never have to wonder what happens next.

The Middle Is Where the Magic Is - The Upside

Market segmentation for professional services reveals a distinct middle ground where independent consultants can thrive. While the top 1% of companies hire prestige firms like McKinsey and the bottom 90% prioritize the lowest price, a specific 9% segment makes purchasing decisions based on passion, unique perspectives, and thought leadership. Success in this middle tier requires moving beyond simple service delivery to consistently demonstrating expertise and building trusted relationships. Transitioning from a practitioner to a CEO mindset is essential for long term growth. This involves carving out weekly time to work on business development and strategic positioning rather than just completing client deliverables. Relying solely on referrals is a common trap. Consultants must evolve their thought leadership and expand their networks continuously to stay relevant. Entrepreneurial success is heavily influenced by peer groups, with approximately 95% of outcomes tied to the quality of one's professional circle. When client work consumes all available bandwidth, it serves as a signal to restructure operations and prioritize the strategic activities that maintain a presence in that high value 9% market segment. A CEO knows when to step off the hamster wheel of delivery to focus on operational pieces that ensure the business survives beyond the current contract. This means investing in personal learning and relationship building even when the calendar is full. The goal is to be chosen for a unique take on a problem rather than being the cheapest option available. Erin Halper emphasizes that these assets must be continuously refined and expanded. By focusing on the middle 9%, consultants can build a sustainable practice that values their specific expertise and passion. This approach moves the consultant away from being a commodity and toward being a trusted advisor who wins work through authority and connection.

Here’s How You Know When You’re Ready to Throw in the Towel - The Upside

Choosing between running a business, working for someone else, or staying home with children is a matter of deciding which type of hard is best for your current situation. Entrepreneurship involves a minefield of challenges, including making hundreds of daily decisions, facing frequent failures, and being fully responsible for your own income and potentially the income of others. It requires constant problem solving and a continuous path of evolution where you are never fully comfortable. The benefits, however, include full flexibility, big impact, a strong sense of purpose, and the ability to build your own culture and hire your own people. Working for someone else presents different challenges, such as fitting into a pre-existing company culture, building someone else's dream, and having your salary and professional growth determined by others. The trade-off is a steady paycheck, the presence of colleagues, and the fact that company-wide struggles usually won't keep you up at night. Staying at home with children offers the ability to be physically present and avoid the childcare crisis, but it can lead to a lack of intellectual challenge and a difficult re-entry into the professional world later. When you feel the urge to burn it all down, you should evaluate your options through a series of specific questions. Consider whether you can afford the path you are on versus the path you want to take. Identify what you stand to gain or lose, and define the best and worst-case scenarios. Ultimately, the decision to pivot comes down to who you want to be and whether you have the choice to make a change. While change is difficult, the fear of future regret often makes the first step toward a new path feel more manageable.

Here’s How Transparency Can Be Your Competitive Edge - The Upside

Transparency in compensation and pricing serves as a powerful tool for professional advancement and community growth. Erin Halper, founder of The Upside, highlights how early career experiences with restrictive employment agreements that prohibited discussing salaries led to resentment and anxiety. This personal history contrasts sharply with the story of Sherri Shepherd and Rosie O'Donnell on The View. O'Donnell shared the specific salaries of the co-hosts, revealing she made $2 million while Joy Behar and Elisabeth Hasselbeck made $500,000. At the time, the network had offered Shepherd only $400,000. This transparency gave Shepherd the leverage to negotiate for millions over her seven-year tenure. The practice of sharing financial data creates a pay it forward culture. Shepherd now shares her earnings with other talk show hosts to empower them. In the context of independent consulting, The Upside community institutionalizes this transparency. Members gain access to hundreds of searchable real-world pricing case studies, 1:1 pricing support, and peer cohorts to cross-check rates. This collective knowledge eliminates the guesswork and financial struggle often associated with solo consulting. By openly discussing what they charge, consultants can ensure they are reaching their full financial potential. The document suggests a specific approach for seeking this information: asking a trusted peer for feedback on a proposal's pricing. Ultimately, transparency is framed not just as a moral value but as a strategic competitive advantage that prevents undercharging and fosters a more equitable professional landscape. It transforms pricing from a source of stress into a collaborative effort that lifts the entire group. This shift from secrecy to openness allows professionals to move from corporate life into consulting with a renewed sense of purpose and financial security. Erin Halper uses her platform to advocate for these values, drawing on her experience as a leading authority on independent consulting and the future of work.

Here’s How to Think Creatively About Pricing in a Down Market - The Upside

Independent consultants often encounter budget freezes or tightened spending during market downturns. Instead of losing a lead entirely, consultants can maintain momentum by identifying non-monetary forms of value that benefit their business or personal needs. A primary example involves bartering services for physical products or specialized skills, such as trading a strategy session for a custom-made item. This approach ensures both parties receive high value without a cash outlay. When a client lacks the budget for a full fee, consultants should look for strategic assets that contribute to long-term growth. These include direct introductions to specific internal stakeholders or external leads, which can shorten future sales cycles. Marketing assets are also highly valuable, such as securing a detailed case study, a testimonial from a senior executive, or a feature in the company's newsletter or podcast. Other creative options include access to hosted meeting spaces, professional video recordings of workshops, or social media promotion from high-profile executives. If the client produces a service or product the consultant already uses, accepting that as partial or full payment can bridge the gap. The core strategy is to think beyond the hourly rate and focus on win-win scenarios that build brand equity and pipeline during lean periods.

How and Why Being in Demand Matters for Your Business - The Upside

Creating demand for a consulting business relies on intentional positioning rather than luck. Using the example of 12 Matcha in NYC, the core strategy involves six specific levers that any independent professional can use. Visibility comes from press and social media coverage that highlights quality and sourcing. It is about being seen in the right places by the right people. A tight niche means not trying to be everything to everyone. This is exemplified by a menu with only six items, which signals that the business is the go-to expert for a specific need. Authority is built by obsessing over the craft and being transparent about specialized processes, such as custom water filtration systems. It is about nerding out on the details so clients trust the expertise. Boundaries are essential for maintaining identity and authority. This means refusing to serve products or take on work that does not fit the core mission, such as a matcha shop refusing to serve coffee. Pricing should reflect value and quality without being inaccessible. This helps avoid being a one-time viral trend and instead builds a base of repeat customers. Finally, controlling supply by having limited availability naturally drives up demand. This is basic economics where scarcity increases perceived value. When these factors align, the power balance in client relationships shifts significantly. Clients treat the consultant as an authority rather than a pair of hands. They become more respectful of the consultant's time and are more receptive to higher price points. This approach fundamentally solves the primary challenge of client acquisition. Instead of the consultant constantly chasing leads, prospects begin to line up for the opportunity to work with them. This shift allows for more autonomy and a renewed sense of purpose in a consulting career.

How do you get through the hard days, weeks, and months? - The Upside

Entrepreneurship often involves periods of isolation, financial stress, and intense self-doubt. This discussion highlights how independent consultants and CEOs navigate these difficult stretches through community support and intentional self-care. Key strategies include shifting environments by going outside or to a cafe, engaging in physical activity like Pilates or hiking, and practicing radical self-compassion. Members emphasize that building a business is a long-haul effort where results germinate over different time horizons, making it essential to balance hard work with permission to pause. Tactical advice includes creating a pump up one-sheet of inspirations, committing to five non-negotiable daily tasks to maintain momentum during low-energy periods, and using community spaces to verbally process overthinking spirals. The consensus is that vulnerability is a strength that fosters connection, and feeling off track is often just a sign of growth rather than failure. By naming feelings and allowing for physical releases like exercise or even a midday nap, founders can move through the energy of a bad day without letting it derail their long-term vision.

You Deserve to be Acknowledged - The Upside

Erin Halper, the founder of The Upside, concludes 2025 by highlighting the importance of recognition for independent consultants. She details a community event led by Eduardo Placer, founder of Fearless Communicators, called an Acknowledgement-A-Rama. This session was designed to help members feel seen and heard, providing an emotional boost at the end of a year marked by global turmoil and professional challenges. The core of the message is a series of direct acknowledgments aimed at the independent professional. Halper recognizes the difficulty of showing up and moving forward when the world feels unstable. She emphasizes the impact of small gestures and the value of paying knowledge forward to help others. A key theme is the risk involved in trying new things. Halper acknowledges the determination required to launch new initiatives, regardless of whether they result in success or failure. She also touches on the necessity of shedding baggage, specifically letting go of people or situations that hinder progress. This process of letting go is presented as a difficult but essential step in personal and professional evolution. Furthermore, the text reinforces the idea that believing in one's own ability to succeed is the most secure bet a professional can make. The message connects personal identity to business success, stating that leaning into uniqueness is a strategic advantage. Halper argues that a consultant's unique story and knowledge are often more valuable than they realize. By validating the struggle of building a business, she offers a sense of solidarity to those navigating non-traditional career paths. The reflection ends with a call to maintain core values and keep dreaming about future possibilities. This year-end wrap-up serves as both a psychological reset and a strategic reminder that resilience and authenticity are the foundations of a successful independent consulting practice.

How to Advance in 2026 - The Upside

Success in 2026 is all about craft. This shift is a reaction to a market flooded with low-quality AI content and impersonal services. Clients are moving away from mass-market solutions and looking for boutique, high-touch, human experiences instead. It is like choosing a local bistro with a unique chef over a big steakhouse chain. To win, professionals need to lean into their unique stories and sharpen their specific value rather than just chasing volume. Building quality relationships is now more important than quantity. This means more in-person coffees and small gatherings instead of just digital noise. While AI is great for making operations smoother and helping clients improve their own workflows, it should not replace your actual voice or talent. The main idea is that people do business with people, so trust and curation are the best ways to stand out. This approach moves away from the constant experimentation of the last few years toward a more patient and curated business model. By focusing on highly personalized outreach instead of mass emails, consultants can become the type of partners people actually want to work with. This move toward quality over quantity suggests that the most successful people will treat their work like a curated art form, focusing on deep impact rather than just a wide network. This focus on craft also serves as a necessary break from the exhaustion of the post-pandemic years. It allows for more white space and calm in a professional's schedule by removing the pressure to reach as many people as possible. Instead of the hustle culture of 2025, the coming year rewards those who take the time to create something soulful and intentional.

Why a “Craft” Approach Will Win in 2026 - The Upside

The year 2026 marks a shift toward a craft-based approach in business, moving away from the high-volume, low-quality tactics that have dominated social media and outreach. This philosophy emphasizes quality over quantity in content, outreach, and service offerings. In a market flooded with slop and generic automated messages, a curated and thoughtful approach becomes a significant competitive advantage for independent consultants and service-based businesses. The core of this strategy involves rejecting the more is better mentality. Instead of focusing on tripling business through gimmicks or mass LinkedIn pitch-slapping, professionals should prioritize reaching the right people with highly personalized interactions. This trust-based model relies on better positioning and messaging rather than chasing followers or likes. Practical implementation of the craft approach includes three specific tactics. First, integrating Loom into the tech stack allows for personalized video messages that humanize outreach and cut through digital clutter. Second, adopting a gifting strategy outside of the traditional December holiday season helps maintain relationships. Sending thoughtful gifts or handwritten notes between February and September shows genuine care and acknowledgment of a partner's value. Third, business development must become highly specific. This requires spending 30 to 60 minutes researching a prospect's digital footprint, listening to their podcast interviews, and finding common ground before making contact. By focusing on being better rather than just being louder, experts can distinguish themselves from the noise. The craft approach is about intentionality in every touchpoint, ensuring that every piece of content and every outreach attempt reflects a deep understanding of the recipient's needs and values. This slow and curated method is what clients and stakeholders are increasingly seeking in an era of digital exhaustion.

How to Succeed at Business Development - The Upside

Business development in 2026 requires a return to high-touch, personalized outreach to cut through the noise of AI-generated slop. While automation allows for reaching hundreds of people quickly, it carries significant risks including reputation damage and making poor first impressions. The most effective strategy involves spending more time on fewer, highly-targeted prospects rather than spraying and praying. A winning outreach structure consists of three specific components. First, Why them? requires demonstrating deep research into the recipient's work, values, or recent activities to prove the message isn't generic. Second, Why you? should humbly state your vision and current business stage to establish peer or mentor status. Finally, What's your agenda? must clearly define the mutual benefit and specific goals of the interaction. This approach prioritizes human-to-human connection and intentionality, which are increasingly rare in a landscape dominated by LinkedIn DMs and automated email sequences. Success in the current market comes from acting as a human and avoiding the generic language that now characterizes most professional outreach.

Land More Business by Being Proactive in This Way - The Upside

Existing and former clients rarely spend time wondering about a consultant's additional capabilities or availability. This lack of awareness means significant business opportunities often go unnoticed unless the consultant initiates the conversation. Proactively suggesting new ways to collaborate transforms the relationship from a transactional service provider to a valued strategic partner. This approach involves staying curious, sharing relevant industry insights, and identifying solutions before the client explicitly asks for them. Effective outreach can be framed around observations, data trends, or new solutions developed for similar clients. While many consultants hesitate to reach out for fear of being a nuisance or assuming budget constraints, clients often view these suggestions as a relief. Working with a trusted, proven partner eliminates the risk and effort of finding and vetting new talent. By raising their hand first, consultants can solve problems the client may have been avoiding due to a lack of time or resources. This proactive behavior demonstrates that the consultant is thinking about the big picture and is committed to the client's long-term success.

This Long-Forgotten Lead Gen Strategy Is Still Timeless (and Opens Big Doors) - The Upside

Digital noise and AI-driven outreach have made it harder than ever to stand out. Moving back to analog methods like unique gifting offers a way to bypass the clutter and build genuine connections with high-value prospects. This approach prioritizes quality over quantity by focusing on a small list of dream companies where you can provide significant value. Success depends on shifting the focus from your own brand to the recipient's interests and identity. The process begins by identifying ten target companies and the specific decision-makers within them. Using tools to research their hobbies or public statements helps tailor the outreach. The core of the strategy is sending a physical gift accompanied by a handwritten note and a clear call to action. Effective gifts are those that celebrate the recipient, such as a high-quality notebook with their name or custom items featuring their company logo. Generic office swag with your own logo is less effective because it feels like a standard marketing play rather than a personal gesture. Platforms like Zazzle and Etsy make it easy to source creative, inexpensive items like custom poker chips or mini basketball hoops. The financial investment is relatively low, ranging from $15 to $50 per prospect. Even on the higher end, a $500 campaign targeting ten people can yield an 80% meeting rate and lead to multiple closed contracts. A critical final step is the follow-up, which should happen within two days of delivery to demonstrate proactivity. Including a QR code for easy calendar booking or a small coffee gift card can further lower the friction for the prospect to say yes to a meeting. This timeless strategy works because it treats potential clients as individuals and creates a memorable first impression that digital messages cannot replicate.

The “Park Bench” Theory - The Upside

Three Easy Fixes To Improve Your Proposal Close Rates - The Upside

Closing more deals often requires small, tactical adjustments to the proposal stage rather than a complete business overhaul. Many consultants find that deals die after a successful discovery meeting because the momentum stalls or the client's priorities shift. To combat this, one effective fix is adding a "Good Until" date at the top of every proposal. This date, usually set for one or two weeks after the proposal is sent, creates a sense of urgency and gives the consultant a professional reason to follow up. It also serves as a safeguard for the consultant's schedule and pricing, making it clear that availability and rates are not permanent. This approach communicates fair boundaries and establishes the consultant as a professional authority. Another critical addition is a section titled "What we'll consider a success." This section allows the consultant to reiterate the client's desired results and describe the specific transformation they can expect. It is essential to tie these outcomes to the Four Pillars of Value: growing revenue, cutting costs, gaining access to specific expertise or networks, and solving major headaches that hinder growth. By focusing on these core drivers, the consultant builds trust and ensures that expectations are aligned from the start, which also protects the relationship if the project scope begins to drift later on. Finally, consultants should transition to a live proposal review process. Instead of emailing a PDF and hoping for a response, presenting the proposal in a meeting significantly increases close rates across all industries. This requirement should be introduced early in the discovery phase as a standard part of the consultant's proven process. If a client insists on an email, the consultant should frame the live review as a high-touch service that ensures 100% alignment and attention to detail. This shift reinforces the consultant's role as the CEO of their own business and an expert who knows the best way to achieve results for their clients.

Nobody Knows What They’re Doing - The Upside

Erin Halper, the founder of The Upside, addresses the pervasive myth that successful entrepreneurs and consultants have everything figured out. Based on her career path through private equity and independent consulting, she asserts that even the most celebrated figures on magazine covers are often navigating the same uncertainty as everyone else. This perspective is meant to relieve the pressure professionals feel to appear perfectly polished or further along in their business development than they actually are. She notes that the feeling of needing to have it all figured out is often the very thing holding people back from taking necessary risks. The core of the message warns against the noise of secret formulas and coaches promising easy growth through "buy now" programs. Halper argues that these shortcuts are often distractions from the fundamental work of building a business. True success is described as a non-linear process involving the refinement of offers, the establishment of healthy boundaries, and the consistent service of clients. She emphasizes that curiosity and patience are more valuable than a rigid master plan. Success is not about cracking a code but about valuing your expertise and serving clients well over the long term. During her appearance on the Development Nerds Podcast, Halper and host Candice Mitchell explore how to identify unhealthy business role models and why the loudest voices in the industry aren't necessarily the wisest. They point out that businesses appearing explosive from the outside often lack internal stability. The takeaway for independent professionals is to prioritize alignment over external validation. Success comes to those who are willing to keep trying different ideas, clients, and communities until they find what sticks, maintaining a willingness to learn from every mistake along the way. Ultimately, the most successful entrepreneurs are simply those who are willing to say they don't know the answer but are committed to figuring it out.

Five Ways to Practically Evolve Your Business in the Age of “AI Everything” - The Upside

Independent consultants are currently navigating a significant shift where AI impacts every industry and geography regardless of the specific niche. To adapt practically, business owners should first look at using AI to handle the operations side of their work. This includes managing finance, systems, tech setups, and the creation of proposals. Automating these repetitive tasks buys back several hours every week which can then be reinvested into front end growth activities like networking, nurturing leads, and high level client delivery. Using platforms like Relay.app is a specific way for scrappy consultants to build mini teams of AI assistants that possess diverse skills and expertise without the overhead of human employees. Another strategic path involves adding AI-lite services to an existing portfolio. This might mean selling custom chatbots as an add-on or offering AI advisory alongside traditional CEO leadership coaching. You do not need to be a deep technical expert to provide these services; staying curious and learning the basics is often enough to guide clients who are hungry for AI integration. For those who prefer a different route, positioning yourself as the human antidote to AI is a viable strategy. Many clients still value the human touch and perceive AI generated work as low quality or cheap. Focusing on what AI cannot do is essential for maintaining long term relevance in a crowded market. AI cannot show up in person at events, build deep interpersonal relationships, or use a personal Rolodex to make warm introductions. It also lacks the ability to read a room during a sensitive meeting or create something entirely original from scratch. Consultants who stay curious and position themselves as AI leaders in their specific fields will become the go-to co-pilots for their clients. Ultimately, AI will not replace the consultant who chooses to evolve their craft and lean into their unique human strengths.

Nobody knows what they’re doing (and that’s normal)

How To Get a Yes, Faster - The Upside

Following a massive LinkedIn Live event with over 22,000 registrants, Erin Halper addresses a common struggle for independent consultants: how to get clients to say yes faster during discovery calls. Most consultants make the mistake of focusing on their skills, toolkits, and credibility. They spend the call pitching their background and talking more than they listen. This approach treats the client's initial request as the final word, which often leads to a slow sales cycle or a 'no' because the true value isn't clear. To accelerate the closing process, consultants must shift their mindset to that of a detective and a partner. This involves staying curious and not taking the company's initial request at face value. The goal is to help the client define the problem in a way that links directly to a specific result and solution. This process is guided by the Four Pillars of Value: growing revenue, cutting costs, providing access to specialized frameworks or networks, and solving a growth-blocking headache. In practice, this means asking deeper questions like 'Why is this important right now?' or 'Why do you think this happened?' For example, if a client asks for AI deepfake training, a consultant using this framework would uncover that the real issue is a $350,000 loss from a previous scam. By identifying that the client actually needs to prevent future high-figure costs and gain access to rare expertise, the consultant can propose a broader, more valuable solution than just a single training session. This method ensures the consultant is seen as a problem solver rather than just a service provider, making it much easier for the client to commit quickly.

How To Get a Yes, Faster - Part 2 - The Upside

Effective discovery calls for consultants hinge on moving away from a sales focused mindset toward a partnership oriented approach. Instead of leading with a pitch deck or a list of services, successful consultants prioritize listening and asking targeted questions. This strategy positions the consultant as a detective who uncovers the core business drivers behind a client's immediate needs. The process is guided by the Four Pillars of Value, which state that every client objective is ultimately about growing revenue, cutting costs, gaining access to specialized resources, or solving a headache that blocks growth. No matter what a client initially says they need, their motivation will always fall into one of these four categories. The framework for a high converting discovery call follows three distinct stages. First, the consultant must define the problem. This involves asking why the client reached out and why the issue has become urgent at this specific moment. Second, the consultant clarifies the desired result. This stage focuses on the client's vision for the next quarter or year and identifies the obstacles preventing them from reaching that goal. Crucially, this part of the conversation should address what the client stands to gain from success and what they risk losing by maintaining the status quo. Third, the consultant offers a solution by exploring what has been tried in the past and identifying the specific gaps in the current team's capabilities. Erin Halper, founder of The Upside, emphasizes that being curious and reading between the lines makes a consultant the obvious choice. By using this structured inquiry, consultants help clients redefine their problems in terms of business value. This approach builds trust and demonstrates a deep understanding of the client's challenges. The goal is to ensure the client sees the consultant as a trusted problem solver. This methodology ensures that the proposed solution is directly linked to the client's most pressing financial and operational goals, leading to a faster and easier agreement.

Three Ways to Approach Discounts, Without Diminishing Your Value - The Upside

Discounting professional services often creates a permanent psychological anchor that makes it difficult for a client to ever pay full price in the future. This phenomenon is similar to retail consumer behavior where brands like the Gap train customers to only shop during sales, whereas brands like Sézane maintain value by rarely discounting and creating scarcity. When a consultant offers a lower rate, they are not just losing immediate revenue but also lowering the likelihood of receiving full-price referrals. Most clients who negotiate for a lower rate will expect that same rate for all future work and will likely describe your services to their peers as affordable rather than high-value. To combat this, there are three primary strategies to handle budget pushback without devaluing the work. The first is scaling down the scope. This approach treats the budget as a fixed constraint and adjusts the deliverables to match. It preserves the hourly or project-based rate while offering a smaller package that fits the client's financial limits. The second strategy is repositioning the return on investment. Often, a client's hesitation isn't about the total cost but a lack of clarity on the value generated. Reframing the conversation to compare the investment against the expected business outcome, such as a $50,000 fee for $2 million in new conversions, shifts the focus from cost to profit. The third strategy is holding firm on the original price by emphasizing the unique assets being brought to the table, including specific frameworks, industry relationships, and years of experience. If the client truly cannot afford the fee, offering a referral to a junior professional serves as a polite way to maintain your premium status. This demonstrates that your specific expertise has a fixed market value that cannot be negotiated. For situations where a discount is absolutely necessary to close a deal, it is vital to keep the full price visible on all proposals and invoices. By crossing out the original price and showing the discounted rate, the consultant provides a constant visual reminder of the true value being delivered.

How Do You Know You’re Charging the Right Prices? - The Upside

Determining the right price for consulting services relies heavily on analyzing proposal close rates and the speed of client decisions. A common mistake among consultants is viewing a high close rate, such as 90%, as an unqualified success. In reality, a near-perfect close rate suggests that services are likely underpriced. The core framework for adjusting rates centers on three distinct outcomes. A quick "yes" indicates room to increase prices. Constant pushback followed by a "no" typically points to a Pricing-to-Value misalignment, where the communicated value doesn't justify the cost. The ideal scenario occurs when a client pauses to consider the proposal before eventually agreeing, signaling that the price is high enough to be significant but fair relative to the value provided. Quantitatively, specific benchmarks help guide adjustments. If 80% or more of proposals are accepted, prices should be raised by 10% to 20% for future bids. Conversely, a close rate of 10% or lower suggests a need to either improve value communication or reduce pricing by 10% to 20%. The "sweet spot" for pricing is a 20% to 50% close rate. This range confirms that the consultant is not building a volume-based business but is instead maintaining a high-caliber practice where the offering is not for everyone. Accepting that "no" is a natural part of a healthy pricing structure allows consultants to maintain autonomy and avoid the pitfalls of a high-volume, low-margin model. This approach shifts the focus from simple sales volume to strategic value alignment, ensuring that the consultant's time is compensated at a rate that reflects their actual impact. Erin Halper, founder of The Upside, emphasizes that pricing is a tool for positioning. Lowering prices might increase community membership or client count, but it risks transforming a specialized advisory into a volume-driven business, which often conflicts with the goals of independent consultants seeking flexibility and purpose.

Your “Not” List - The Upside

Defining what you don't do and who you don't serve is a critical step for savvy business owners. While most consultants focus on their niche, the most successful ones create a "not" list to protect their energy and long term growth. This list includes specific parameters like personality traits, company size, industry, and red flags. By filtering out wrong fit clients, consultants can focus on repeatable work with people they actually enjoy. Erin Halper uses her own business, The Upside, as a case study for this methodology. She excludes B2C businesses, large agencies, and part time consultants. Her community is specifically for high caliber, generous professionals who see others as colleagues rather than competitors. One notable operational choice is her refusal to do 1:1 sales calls. Instead, she hosts an Open House to vet mutual fit in a more human way. This approach prioritizes substance over flash and ensures the community remains high caliber and generous. The "not" list acts as a protective barrier for your business model. Most independent consultants avoid creating one because they fear leaving revenue on the table. However, wrong fit clients often lead to confusion and frustration, which ultimately hinders long term success. A well defined list might include parameters like scope length, payment terms, or even gut feelings. Ultimately, a "not" list isn't about being restrictive for the sake of it. It is about building a business on your own terms and avoiding the drain of misaligned clients. By being clear about who you are not for, you become much more attractive to the right fit clients who value "real" growth and "real" care. This curation process leads to a more focused and relevant business environment where everyone is invested in each other's success.

The #1 Newsletter for Independent Consultants

Erin Halper, founder of The Upside, provides a comprehensive archive of strategic advice tailored for independent consultants and fractional leaders. The content focuses on the operational and growth aspects of running a consultancy, specifically addressing common hurdles like pricing, sales velocity, and client management. Key resources include the Wednesday Wisdom newsletter, which covers topics ranging from business development and lead generation to technical operations and AI integration. Specific tactical advice includes methods for improving proposal close rates and strategies for getting to a yes faster in the sales cycle. The archive emphasizes the importance of positioning, suggesting that consultants create a Not list to clearly define their boundaries and service offerings. On the financial side, Halper explores how to determine if pricing is correct and how to offer discounts without diminishing the perceived value of the work. The resources also touch on modern business evolution, such as practically integrating AI into a consulting practice and leveraging LinkedIn for business growth. Beyond individual articles, the platform offers structured tools like a Pricing Playbook and a Lead Gen Made Simple guide. The overall framework encourages consultants to move from a solo mindset to a community-supported model through The Upside's accelerator and membership programs.