Is There a “Right Time” to Start Freelancing? Here Are Some Signals

Know when it’s time to leave your 9–5 job.

Anna Burgess Yang
5 min readSep 1, 2023
A pop art illustration of a clock with a multi-colored background
Image created via Midjourney

“When is the right time to begin freelancing?” is a lot like asking “When is the right time to buy a house?” or “When is the right time to have a baby?”

There’s never a perfect time.

Or if you wait for the perfect time, when you think you’ll have enough clients or have enough in savings, you’ll miss so much opportunity.

I didn’t wait. As a matter of fact, I was thrust into freelancing when I was laid off — like so many other people. It was a way to quickly earn money instead of looking for a full-time job.

But honestly? If I hadn’t lost my job, I would have left it, probably within a few months. The signs were there. I just hadn’t worked up the courage to make the leap yet.

If freelancing is on your mind, here are some things that might help you make a decision.

You think it’s unlikely that you’ll find a dream employer.

One reason people turn to freelancing is that they’re fed up with employers. Usually it’s not just a single employer, but they move from job to job and nothing is the right fit.



Anna Burgess Yang

Freelance Writer. Practical Tips for Solopreneurs. Career pivots are fun. 🎉