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


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.

Or they’re burned by multiple bad employers (which was my case), and the idea of looking for another employer is exhausting. A job hunt can be really long and often demoralizing. And that’s just to find a job, not necessarily the perfect job.

You may start to think that a great employer is elusive. There are so few really great companies out there that really offer everything: great salary, great benefits, great managers, reasonable work-life balance, growth opportunities, etc. And for those unicorn employers? They have hundreds — if not thousands — of applicants. Landing a job there is like winning the lottery.

So then you ask yourself what you’re willing to give up.

And you find yourself saying that you don’t want to give up anything. You think you’ll be frustrated no matter where you go. You’re willing to give up some stability. Freelancing seems like a better alternative.

You have tested the waters…



Anna Burgess Yang

Productivity geek + solopreneur. Niche freelance writer. #5amwritersclub frequent flyer. •