How a Solopreneur Grew from $5K to $15K a Month by Outgrowing Scarcity

Go From “Scarcity Mindset” to Strategic Confidence

Harlow Co-Founder Samantha Anderl on Overcoming the Emotional and Operational Drains of Solo Work

Welcome back to The Wedge, the newsletter for strategic solo business owners.

In her work with freelancers, Samantha Anderl, marketing consultant and co-founder of Harlow, noticed something surprising. Even high-earning solopreneurs making $15,000 to $20,000 a month were asking themselves, what if it all goes away?

Without a steady paycheck, with health insurance to secure, business costs to manage, and administrative tasks multiplying, solopreneurs face pressures that go far beyond client work. Some are emotional: scarcity mindset, isolation, lack of feedback. Others are operational: untracked expenses, missing legal protections, hidden costs that erode profit. Together, these drains shape how solopreneurs price their work, manage risk, and plan for growth.​

In this issue, Samantha breaks down these common challenges of solopreneurship and offers a practical four-point blueprint that solopreneurs can use this year to build stronger systems and create a sustainable business.

Helping Solopreneurs Unlock Growth: Samantha Anderl’s Story

After nearly a decade climbing the corporate ladder, Samantha realized that being a marketing executive was no longer her dream. Long days filled with mergers and acquisitions meetings left little room for the creative building she loved. In 2016 she and her CMO left to start a consulting firm helping early‑stage startups build marketing from the ground up. Within a few years, the firm grew to over $1 million in annual revenue. In the process, Samantha and her co-founder regularly subcontracted work to independent freelancers, giving her a close, practical view into the operational and emotional challenges solo professionals face.

Listening to their struggles inspired Samantha to co‑found Harlow, a “home for freelancers” that combines an all-in-one business platform, a weekly newsletter, and a job board. Today, Harlow reaches more than 11,500 newsletter subscribers, draws roughly 20,000 freelancers to its job board each month, and supports freelancers directly through one-on-one coaching and focused strategy sessions to unlock growth. Alongside building Harlow, Samantha continues to work with a small number of consulting clients.

Navigating the Emotional and Operational Costs of Solopreneurship

Outgrow Scarcity Mindset by Evolving Your Offer

Many solopreneurs carry a persistent fear that work could disappear overnight. Samantha saw this firsthand when she stepped back into consulting after taking a break from it while building Harlow. The market had changed, and the playbook that once worked no longer delivered results.

She refined her positioning through a one-page website that made her role clear: a go-to-market partner for early-stage startups, with scoped offerings and outcomes aligned with her LinkedIn narrative. Within weeks, she secured a $12,500-per-month client.

Her lesson is direct. Market conditions will always shift. Scarcity comes from assuming your current offer is fixed. Confidence comes from knowing you can adapt.

“Scarcity mindset" is saying, ‘What if no one buys this anymore and the work dries up?’,” she said. “When you step into abundance, you’re saying, ‘That’s not going to happen, because I’m always going to evolve and deliver work that’s valuable.’”

Research on career adaptability backs this approach. A study published by the Journal of Vocational Behavior, found that professionals with high career adaptability were substantially more confident navigating market shifts and consistently reported better performance and income stability than those who relied on fixed roles or static skill sets.

Account for Functional Business Costs Such as Health Insurance

Creative professionals often leap into freelancing without realizing that they’ve become their own IT, finance and HR department. They must choose a legal structure, handle bookkeeping, draft contracts, send invoices and pay estimated taxes.

Samantha sees this as one of the most common and costly blind spots.

Ignoring these foundations can carry real risk. For example, sole proprietors are personally liable for business debts, whereas an LLC shields personal assets from most business liabilities.

Health insurance costs can also be a significant and often underestimated expense. Depending on the state, individual coverage can range from roughly $450 per month at the low end to $1,000 or more, with higher costs common in states like California. Lower monthly premiums are often driven by subsidies, many of which are set to expire, pushing expected costs higher in 2026.

(To make healthcare insurance more accessible and streamlined for solopreneurs, Lettuce is planning to launch a dedicated healthcare offering in early 2026. Sign up here to join the waitlist)

When left untracked, these costs erode profitability and amplify stress. Samantha’s approach is to treat them as core business expenses. Once they are visible and planned for, solopreneurs can make clearer decisions about pricing, workload, and long term sustainability.

Counter Isolation by Celebrating Your Own Wins 

Solopreneurship can be isolating in ways many people do not anticipate.

Samantha experienced this shift immediately after leaving her corporate role. She went from leading teams and receiving constant feedback to working largely alone.

“I went from a job where I was constantly getting affirmation, surrounded by people, launching projects and talking in front of the company. My love language is affirmation. That’s how I felt valued.” she said. “When I went out on my own, I missed that.”

Without colleagues or managers to reflect progress back to her, Samantha had to redefine how she measured success or how she found fulfilment at work. Instead of relying on external validation, she began valuing flexibility, control over her schedule, and the ability to choose her work. Today, she coaches solopreneurs to intentionally counter isolation by building community, and celebrating their own wins rather than waiting for external validation. When coaching companies who work with freelancers, she’s always reminding them to rethink how they give feedback.

“A lot of freelancers only get negative feedback,” she said. “When they’re doing a good job, you need to tell them that and reward them. They deserve the same kind of experience that internal employees have.”

Taken together, these interconnected emotional and operational pressures shape how solopreneurs price their work, manage risk, and plan ahead. These pain points are not solved through hustle or sheer motivation alone, but through structure. Below, she outlines a four-part blueprint and shares downloadable resources to help solopreneurs put these systems into place.

Samantha’s Blueprint to Tackle Hidden Drains of Solopreneurship

1. Lay a Real Business Foundation

• Choose the right structure. Forming an LLC or S‑corporation protects personal assets and creates a professional identity. Samantha recommends filing once and setting up separate bank accounts to avoid co‑mingling funds.
• Secure essential health insurance. Health insurance is a core business cost with monthly premiums for individuals can range from roughly $450 to $1,000 or more depending on state and plan. Samantha used a local broker and Solo Health Collective to find coverage tailored to her needs. She suggests re‑evaluating plans annually and counting premiums as a business expense. Lettuce is introducing group-rate healthcare coverage for Lettuce Pro customers starting in early 2026. This is healthcare designed for independent professionals: simpler, more affordable, and actually usable. Learn more about healthcare access through Lettuce.
• Build financial infrastructure. Tools like Lettuce automate payroll taxes and help you elect S‑corp status when it makes sense. Platforms such as Harlow, Invoice Ninja, Fiverr Workspace and Bonsai streamline proposals, invoices, contracts and payments. Samantha stresses that these foundations are “one‑time heavy, ongoing light” investments.

2. Treat Your Business Like a Business

Once the legal and financial foundation is in place, the next step is operational discipline. Samantha’s second pillar asks solopreneurs to start thinking like a CEO. This shift focuses on eliminating friction and investing in support.

• Remove or resource energy drains. Notice which tasks sap your energy and treat them like real business expenses. Samantha hired an executive assistant (EA) to handle scheduling, invoicing and follow‑ups and subcontracted specialized work when it fell outside her expertise. For others, it may mean acknowledging that building a public-facing profile does not come naturally and resourcing that work, whether by hiring help to write, manage LinkedIn, or support a broader social presence. The goal is to free up time and attention for higher-value work by investing where friction shows up.
• Track your income and expenses. Samantha created a simple spreadsheet to list monthly revenue alongside major expenses such as health insurance, software subscriptions, subcontractors, coaching and her executive assistant. This visibility helps her focus on take‑home pay and identify unnecessary drains.

Download Samantha's Sustainable Systems Audit & Income Tracker

3. Shift from Scarcity to Abundance

With infrastructure established and systems running, solopreneurs can address the mindset that shapes every business decision.

• Pivot with confidence: Solo work demands constant evolution. Markets shift, new tools emerge, and what works today will not work forever. Samantha’s view is that this is not a risk unique to freelancers, it is true of any long career.

“As a freelancer, you’re in control of your business,” Samantha said. “One of the things that comes with that is the ability to pivot and change to meet market needs.”

Rather than assuming an offer is fixed, she encourages solopreneurs to stay on top of their field, reskill and upskill as needed, and adjust how they package and present their work. Nothing becomes obsolete overnight. It evolves. Scarcity shows up when people stop adapting. Confidence comes from knowing you can continue to create value, even as conditions change.

• Invest in yourself and grow. Samantha works with a coach for strategic guidance and budgeting. Viewing these investments as operational costs rather than luxuries allowed her to scale sustainably.

4. Activate Your Network

The final pillar turns individual work outward, leveraging relationships as a growth engine.

• Systematic outreach. Samantha coaches clients to list 10–30 people in their network, craft a personal message explaining what they do and who they help, and ask for introductions. Offer something in return—share their work or make a connection. This low‑hanging fruit often yields the one or two new clients needed to reach the next revenue tier.
• Build or be part of a community and grow your network. Samantha recommends joining peer groups like Harlow's community, coworking spaces, or industry Slack channels where freelancers share insights, swap referrals, and celebrate wins together. Regular interaction with other solopreneurs creates accountability and normalizes the emotional ups and downs of independent work.
• Build a simple online presence. Make your work legible with a simple one-page website and a clear, consistent LinkedIn profile. When your role, audience, and offering are easy to understand, visibility helps others hire you or refer you without extra explanation.

The Results

Higher revenue and confidence. Clarifying offers and pricing allowed Samantha to raise consulting rates and maintain a small, high‑impact client roster. One freelancer she coached moved from making $4‑5 k per month to $15k in just five weeks after putting basic systems in place, using a proper invoicing system and activating her network.

• Community impact. Harlow now reaches 11,500 subscribers, supports 20,000 freelancers monthly through its job board and has hosted dozens of sponsored events. Samantha’s frameworks are influencing a generation of solopreneurs to treat their business like a business—building legitimacy, stability and growth.

Samantha’s experience shows that uncertainty is part of solo work, but so is flexibility. Solopreneurship offers real control over how you shape your career, if you choose to use it. Setting up systems make that control usable. Clear positioning allows you to adapt as markets change. Tracking expenses turns guesswork into decisions. Building community replaces isolation with feedback and momentum. When solopreneurs treat their work like a business, they move from reacting to uncertainty to actively shaping what comes next.

Put Samantha’s Approach into Practice

Samantha’s Sustainable Systems Audit & Income Tracker includes

• Hidden costs and systems checklist. Identify overlooked expenses, assess your current systems, and see where your business needs stronger structure.
• Referral and network activation template. Turn existing relationships into a reliable source of new work using a repeatable outreach framework.
• Income and expense tracker. Record monthly revenue and major expenses, with a clear focus on take-home pay after business costs.
• Core Solopreneur Systems: software for key tasks. A practical map of essential systems for invoicing, contracts, bookkeeping, payroll, and client management—so your business runs with the same infrastructure you once relied on as an employee.