It depends! It could take anywhere from tomorrow to 5 years.
Depending on the way you look at it, it either took me 2 years, 7 years, or 16 years.
It was 2 years from the time I decided I was going to fully quit my job, which is when I got a coach to keep me accountable.
It was 7 years since I started to build my expertise in developer education by becoming a Pluralsight author, doing more speaking, and doing technical marketing at night ("moon-lighting").
And it was 16 years since I was 18, before which I WAS working for myself doing website design freelancing. So I guess my career was a regression? 😂
So if you're looking for a straight answer, I wish I could give you one. It entirely depends on your situation and what you want to do.
But there is one big factor I guarantee you'll need to think about: how much money do you need to sustain the transition period? How long can you go without earning income? That's your "runway" and what I like to call your F U Money.
You're going to need a runway with almost every move you want to make, whether that's consulting, SaaS, freelancing, startup founder, and any of the other paths I've previously talked about.
Depending on your risk tolerance, that could be anywhere from 4 months to even a year or more saved up. For me when I quit, I had about 5-6 months of cash plus a host of other levers I could pull that gave me the confidence to say F U to my dayjob.