Is solopreneurship right for you? These are the exact questions to ask yourself before making the leap

I started working as a remote employee back in 2006, long before it was common. I talked to my colleagues during the day, sure, but they were all in an office with cubicles. I worked alone.

Later in my career, I was part of an executive team at a software company, making decisions about budget and strategy.

So when I started my own business in 2022, many aspects felt like a natural extension of the way I’d always worked. 

Most advice about leaving corporate life focuses on the financial safety net: savings, pricing your services, and side hustles. But money isn’t the only reason people leave solopreneur life and go back to a nine-to-five. Some people are genuinely not wired for the day-to-day reality of working alone. 

Before you make the leap, it’s worth being honest about whether the nonfinancial parts of solopreneurship are a fit for you.

You’ll be making every decision

In corporate jobs, decisions get distributed across teams, managers, and leadership. As a solopreneur, every call is yours.

You’ll face decisions daily, without the option for a second opinion. You don’t have a colleague to gut-check an idea or a manager to absorb some of the risk. It’s just you.

Some people thrive on this autonomy. Others find it paralyzing. Procrastination and indecisiveness become real problems when there’s no structure forcing you to make a call. In a corporate job, deadlines and approval chains keep things moving, whether you feel ready or not. When you’re solo, nothing moves unless you do.

What to ask yourself: Will I feel confident making decisions without a team to weigh in, and will I be able to move forward even when I’m unsure?

Loneliness is a real consideration

Solopreneurship can be isolating in a way that catches people off guard. I’ll have entire days go by without a single meeting. A survey from Founder Reports found 26% of solopreneurs feel lonely or isolated. 

Some people manage this through communities, like Slack groups, virtual coworking, or networks. I’ll have an occasional “coffee chat” via Google Meet with solopreneurs I meet online, just to connect with others. But these require effort to maintain, and they’re not the same as having colleagues who share your day-to-day context.

What to ask yourself: Do I feel energized when working with other people, or do I do my best work alone?

You have to sit with uncertainty

Even experienced solopreneurs deal with income volatility, slow seasons, and the ongoing question of whether a particular business strategy will pay off. The difference between “keep going” and “go back to corporate” is tolerance.

In a corporate job, uncertainty is usually someone else’s problem. Your paycheck still clears. In solo work, you absorb the uncertainty directly. It’s hard to think clearly when you’re worried about your business. 

Everyone’s tolerance for risk is different. Even with the most conservative decision-making, you won’t always get it right. And a lot of things are outside your control.

What to ask yourself: How would I feel if I didn’t have enough clients for a month . . . or two?

The financial question isn’t the only question

Solopreneurship is often framed as something anyone can do if they just plan well enough. While it’s true that planning can make a solo business more stable, planning can’t change your wiring. 

Being honest about what solo work actually demands—emotionally and psychologically—is one of the most practical things you can do if you’re thinking about going solo. 

The financial aspects matter, of course. But so do the questions of whether you’ll be okay on the days when the work is quiet, the decisions are yours alone, and the path forward isn’t obvious.

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