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.
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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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