[samwillis]

I pulled that trigger later than I could have, I was earning 2x my salary from my side project before I quit.

At 50% if you can see an upward trend, ~6 months savings, and have a plan that the time will give you to execute, got for it.

[bombcar]

The "main thing" is how hard it would be to get back in the business (i.e, get a job) if the whole thing explodes.

Also if you're going to quit anyway, you might as well ask the company you currently work for if they'll let you go on sabbatical, or part time, or consulting.

That can give you a bit of extra runway/feeling of security.

[valval]

I suppose you can go back to any of the previous points in your CV as a software professional in today’a day and age if you never burned any bridges. Especially so if you make it obvious in your current job that you’re only leaving because it’s time to try your own thing - if it doesn’t end up working, people are likely to be very understanding.

[marginalia_nu]

It's not like I'm doing nothing for these upcoming years.

Dunno what you're doing wrong if you can't land a job with a built-from-scratch internet search engine on your resume.

[HeyLaughingBoy]

But can you pass LeetCode :-)

[bombcar]

In general all you need is an explanation for a break in work history and there are billions that will satisfy interviewers and HR; at worst just say “health reasons” and then sue when you don’t get the job ;) (/sarcasm)