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There’s a popular narrative around starting a solo business: quit your job, take the leap, figure it out along the way. It sounds bold. It also ignores what many successful solopreneurs actually do: start while they still have a paycheck, figure it out, and then quit.
I freelanced alongside my 9–5 for two full years before going solo full-time. That runway gave me time to figure out my offer and ideal clients, build a portfolio, and develop the confidence that I could make it work. As a result, the transition didn’t feel like a free fall.
If you’re thinking about solopreneurship, a side hustle might be a smart way to get started.
The 9–5 is your (temporary) safety net
A side hustle while you’re still employed gives you something incredibly valuable: the ability to experiment without risking your livelihood.
You can determine what services you plan to offer and validate whether there’s demand. You can pitch potential clients, test different pricing, and figure out what “sticks”—all while a steady paycheck covers your bills.
You’re also building proof that you can do the work. Future clients want to see what you’ve already done, not what you plan to do. A portfolio and a few client testimonials go a long way when you’re ready to announce that you’re open for business full-time.
The tough part is juggling both. I had a lot of late nights and weekends when I took on freelance work alongside my 9–5 job. But I knew it wasn’t forever, so it was worth the period of overlap.
Know your number before you leap
Before you quit, you need to know how much you need to earn—and have some evidence that you can get there.
Start by calculating the minimum you need to cover your business expenses, taxes, and your cost of living. This is your baseline, and it’s more useful than a salary comparison because it accounts for the realities of self-employment: quarterly tax payments, software subscriptions, and the fact that you’re now paying for things your employer used to cover.
The day I went solo full-time, I knew what I needed to earn. I didn’t need to replace my 9–5 salary right away (though that was certainly the goal). I also knew how much more work and how many more clients I needed to get from side-hustle status to running-a-business mode.
A side hustle with a paycheck is also the easiest time to build an emergency fund. Set aside your side hustle earnings while your 9–5 covers your day-to-day expenses. By doing this, you can afford to earn less when you initially go full-time as a solopreneur, because you can draw from your savings.
Build your operational foundation
Side-hustle time is when you set up the systems that will run your business. Contracts. Invoicing. A basic website. Pricing. All of these things are easier to figure out when your income doesn’t depend on getting it right the first time.
You’ll also start learning how to manage client relationships on a much smaller scale—like communication and setting expectations around project scope. When you make the switch, you’re able to scale up much more easily.
The jump gets smaller
Starting a side hustle shrinks the gap between employed and self-employed. By the time you leave your 9–5, you’ve already started your business.
Not everyone has the luxury of a gradual transition. Sometimes, a layoff or life circumstances force the issue. But if you have the option, use it.
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A few weeks ago, I was reconnecting with a former colleague from my higher education days, and we started talking about our current work. At one point, she paused and said, “I love the path you’ve taken, but if you’d asked me 10 years ago, I would have said you’d definitely end up a dean somewhere.”
Honestly, there was a time I thought so, too.
For years, that path felt not only plausible, but likely. I loved universities: the intellectual intensity, the sense of mission, the complicated human systems. I was drawn to institutional leadership and to the challenge of helping organizations navigate moments of conflict, ambiguity, and change. I understood academia intuitively and knew how to function effectively within it. There was a version of my life that felt visible and coherent long before it actually happened.
Instead, my life unfolded differently. I left higher education, built a coaching and consulting practice, and now spend much of my time in conversations that are more psychologically exploratory and relationally intimate than the work I once imagined myself doing.
What struck me about my colleague’s comment was that it did not evoke regret exactly. Instead, it prompted reflection on all the paths I did not take and all the selves I did not become.
I suspect many high-achieving adults quietly carry some version of this experience. At a certain point in adulthood, particularly for people who have built meaningful careers and substantial lives, there is often a dawning awareness that success narrows identity. By becoming one version of ourselves, we inevitably relinquish others.
The identity journey
When we are younger, identity feels expansive. Multiple futures remain psychologically available at once. We can imagine radically different versions of our lives because, in some meaningful sense, those possibilities still exist. Over time, however, adulthood requires consolidation. We choose careers, partners, cities, institutions, obligations, and areas of expertise. We become increasingly recognizable to others and increasingly fixed in our own understanding of ourselves.
Developmental psychologists have long observed that identity formation depends not only on exploration, but on commitment. The problem is that our culture tends to frame success almost exclusively in terms of acquisition: the title earned, the family built, the expertise gained, the opportunities secured.
Far less attention is paid to what success requires us to relinquish.
I see this often in my coaching work, particularly among highly capable leaders. These are people who are accomplished, respected, emotionally intelligent, and deeply competent. Many have built objectively meaningful lives and feel genuine gratitude for them.
Our neglected selves
And yet, beneath that gratitude, there is often another emotional current that can be difficult to name.
Sometimes it surfaces unexpectedly. A client rediscovers an old creative project and feels emotional in a way she did not anticipate. Another realizes she cannot remember the last time she did something that was not productive, strategic, or useful. Someone else reflects casually on a life she once imagined for herself and finds she cannot stop thinking about it afterward.
These moments are rarely about dramatic regret. More often, they reflect an encounter with neglected aspects of self.
I think this experience is particularly common among adults whose identities have become highly organized around competence. Competence is enormously adaptive. Organizations reward it, families rely upon it, and entire careers are built upon it. But over time, many high-achieving people become so practiced at functioning that they lose contact with dimensions of themselves that are less externally rewarded: curiosity, creativity, spontaneity, solitude, even simple aimlessness.
This is not because those capacities disappear entirely. More often, they stop being reinforced.
Midlife frequently sharpens awareness of this dynamic. Careers stabilize. Children grow older. External urgency decreases just enough for people to hear themselves think. And in that quieter space, many encounter an unsettling realization: Achievement did not exempt them from being human. They still possess longing, ambivalence, contradiction, grief, and desire. They still wonder who they might have become under different circumstances.
Beyond reinvention
Importantly, I do not think the healthiest response to this realization is necessarily reinvention. Contemporary culture tends to romanticize dramatic transformation in ways I find psychologically simplistic. Most adults do not need to abandon their lives in order to reconnect with themselves. More often, the task is subtler: to become less psychologically rigid inside the life one has already built.
That may involve reclaiming neglected forms of creativity or pleasure. It may involve loosening identities that once provided status or security. In some cases, it simply means acknowledging an uncomfortable but profoundly human truth: Every meaningful life contains unrealized possibilities alongside fulfilled ones.
When I think now about the paths I did not take, I do not feel consumed by regret. Mostly, I feel respect for the reality that every meaningful commitment narrows as much as it deepens.
Perhaps maturity depends, in part, on learning to tolerate both truths at once: gratitude for the life we have built and curiosity about the selves we did not become.
Chances are, you’re working hard, hustling along, and doing your best to stay ahead of things. But when you strive for success, you can risk burnout by concentrating on a limited definition of success. It’s possible, however, to reduce the likelihood …
