How to Know When to Pursue Your Side Gig Full-Time

The number of full time independent workers in the United States grew from 13.6 million in 2020 to 27.7 million in 2024, according to research by MBO partners. Eighty four percent are happier working on their own, reporting better health and security. Once seen as a risky professional path, forging your own path is something even senior corporate leaders are now pursuing to gain control over their time, their income, and who they want to work with.

So why aren’t more people quitting? Figuring out the right time to make the leap can be one of the most complicated aspects of this choice—and many people get that timing wrong.

One of us (Katrina) quit her job at age 23 and walked away from a six-figure opportunity at a Magnificent Seven tech company to become a solopreneur writer and travel the world. At least that was the plan; instead, she found herself working at Starbucks three months later. From there, she built her network by creating new connections and opportunities—eventually landing contract work with companies like HubSpot, which led to a role at Digital Press working with entrepreneurs, then to startups like M1 Finance, and eventually to Category Pirates.

Another one of us (Eddie) waited until age 43, when he was a senior partner at a consulting firm, to launch a solo gig—long after he had ample financial and professional capital to quit. Looking back, he realizes he could have left years earlier—and the delay probably cost him millions of dollars in potential incremental income and precious family time.

The final author (Christopher) made the leap at age 38 after being chief marketing officer of Mercury Interactive, which had just been acquired by Hewlett Packard for $4.5 billion dollars in 2006. It might have seemed early, but after starting a company at 18, being CMO of three public tech companies, and racking up over four million miles on American Airlines, he was ready for something different.

If you’re pursuing a side hustle that seems to be gaining traction, you’re probably grappling with this question yourself: Is there a way to calculate the right time to quit your day job?

It’s a question we’ve researched, consulted on—and considered deeply before making the leap ourselves. Our business, Category Pirates, has begun offering coursework and publishing a newsletter that focuses on this pivotal decision, and we’re currently in the final stages of writing a book on the topic.

While there is no one-size-fits all answer, our work with executives and leaders who’ve successfully made the leap highlights five questions to determine if you are ready to jump.

Can cash flow from your side hustle sustainably exceed your main hustle?

Ideally you have a sustained track record of doing this, but your side hustle trajectory, pricing power, scalability, and word of mouth can help you make the leap a bit earlier. A strong trajectory can be enough to estimate the potential of your side hustle if you gave it your full attention and time. Your side hustle must have pricing power, which is the most truthful signal of demand. New automation tools like Zapier can help you scale your side hustle without just adding time or labor since how you sell (your business model) matters more than what you sell (your offer). Finally, your side hustle must generate word of mouth in an organic and easily amplifiable way.

Dickie Bush was making $200,000 per year at BlackRock in his mid-twenties. He quit BlackRock 14 months after launching a digital writing business with Nicolas Cole. By that point, it was paying him four times his salary and showed a solid trajectory, with increasing pricing power, ability to scale, and digital word of mouth. Now their business generates more than $6 million dollars in revenue.

Does your superpower generate a 10x outcome?

A 10x outcome is a commonly used benchmark in management consulting; it refers to a client getting a revenue, profit or valuation result directly from your work that is at least ten times more than it costs.

What’s your superpower? Defining this is essential—and not as easy as you think. Hint: it has nothing to do with your title, pedigree, or resume. Your superpower must be a unique ability that’s easily quantified in the marketplace by others.

Holley Miller was the director of global brand for Allergan, the pharmaceutical and medical device company, when she built and executed a category design strategy that quadrupled revenue for a product from $25 million to $100 million in four years. She did it by radically changing their marketing—by reframing and naming a different end user problem instead of just marketing features and technology. As a result, end users and physicians saw Allergan’s offer as a category of one with no substitutes. Revenue quadrupled without adding incremental sales reps or dramatic increases in operating expenses.

Miller realized her ability to frame, name, and claim a radically different strategy in med tech was quite rare and the outcomes she generated were exponentially larger than her mid-six-figure salary. She received confirmation of this when competitors began calling to poach her to their teams. So instead of being an executive, she’s now the founder and president of Grey Matter Marketing with a team of 11 utilizing her superpowers on her own terms designing new categories for companies in life sciences.

Do you have enough capital—and the right kinds?

Money set aside is a great safety net, but you need less than what you think—it costs about $10,000 to $40,000 to actually launch a business, on average—and money alone is insufficient. You need three other types of capital. Reputation capital is a track record of repeatable outcomes for a specific problem and the type of clients you are known for serving. Relationship capital is having three types of people in your corner, including those who can see the upside you overlook, loved ones who won’t lie to you, and fellow creators who love to jam with you. Intellectual capital is knowledge you have converted into an asset others can access, pay you for, and achieve outcomes while you are asleep. This can be books, courses, diagnostics, frameworks, or tools that you can monetize with no time or for an extreme price premium on your time.

Jeff Klimkowski wanted to be an investment banker since the ninth grade and realized his dream at Deutsche Bank for 13 years. But he walked away from seven figures in deferred compensation and a looming promotion to managing director to pursue another dream he had with his friends from elementary school, Dude Wipes.

Dude Wipes is the category king of flushable wipes, which Jeff co-founded with his childhood buddies Sean Riley and Ryan Meegan, the CEO and CMO of Dude Wipes, respectively. They were living together after college and realized that for guys who love beer and burritos, regular toilet paper wasn’t going to cut it. They started this as a side hustle over 10 years ago. Sean and Ryan had 9 to 5 jobs and would pack and ship wipes from 6 PM to midnight. Jeff would provide working capital with his investment banking bonus checks. They scored an investment from Mark Cuban on Shark Tank, who bought 20% of the company.

Humor was their superpower. They were willing to make honest jokes about hygiene via social media that would never make it past conservative marketing departments and nervous legal departments at a Fortune 500 company. Soon after, Dude Wipes was growing fast enough that Jeff had to make a decision. Jeff had a reputation as both entrepreneur and investment banker, massive encouragement and support from his boss, and deep expertise in M&A and capital markets—all qualities that would serve him well as CFO of Dude Wipes. As Sean said, “You can always go back and get another investment banking job.” Dude Wipes did $219 million in retail revenue in 2024 and just recently closed a significant minority investment from a leading consumer private equity firm.

Have you mastered your emotions?

Without emotional regulation, it’s hard to get the economics right. The hardest part of quitting isn’t inconsistent cash flow but the constant self-doubt, imposter syndrome, and loneliness. Your emotions can wreak havoc on your pricing by causing you to undervalue your product or service and offer discounts before a customer even asks.

Nick Bennett teaches other solopreneurs how to make the leap, by providing concrete strategies to scale but also coaching to manage all the negative voices and emotions. When Nick was building his business, he realized that running with others on the same journey was crucial. He built a text thread with three other entrepreneurs that eventually grew to a Slack channel of over 50. While he was successful in his coaching and consulting, he realized the power of community and saw an opportunity to meaningfully raise his price vis-a-vis his time. He and his partner created an offer that generated $30,000 in one weekend.

Does your commitment to your craft and mission exceed your need for kudos and money?

If you’re a writer, you must find joy in becoming a better writer even if your writing goes nowhere. You must be clear about and so committed to your mission that you are willing to walk away from money that doesn’t align with your mission. You must love the problem you solve more so than the solution you offer. This ensures you will have the perseverance to innovate and increase the odds of outcomes for your clients. Love of your craft and mission always leads to greater economic abundance.

Danny Bauer helps school principals achieve massive student and culture outcomes. Adam Frankl helps developer-facing startups rapidly scale and secure their next round of funding. Both had successful solo consulting businesses, but both were so devoted to their craft they kept innovating. Now both run six-figure digital communities full of their people that they can help at scale and serve as a pipeline for their consulting. Danny launched a top-ranked podcast and Adam wrote a best-selling book in his niche.

Based on our work in the space, we expect the number of independent workers to double in a decade. Personal and financial freedom are too appealing, especially as job security at large employers in business and government wanes. The rise of single-person households from 8% in 1940 to 28% in 2020 makes it easier to go independent with less people to provide for. But the pull to create will accelerate this transition. Our data shows 77% of U.S. workers would love to be “paid to create.” Millions will remember how creative they were as children, figure out they can be paid to create as adults–and then make the leap.

Copyright 2025 Harvard Business School Publishing Corporation. Distributed by The New York Times Syndicate.

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