I quit my job about 6 years ago. I had savings to last me 2 years.
At first I thought I was going to do freelance work, but the longer I didn't start doing that the more I didn't want to do it. So after a year or so of playing with new tech and starting several personal projects which didn't turn into viable businesses, I began making some money with a website.
Because that profitable website and others I built afterwards weren't actually that profitable, 2 years after I quit, I had to do some freelance work to not run out of money. I had to do 3 years of small freelance gigs while growing an online business. So for me it was 5 years before I could pay myself without having to sell my services.
Not knowing from the beginning what I really wanted to do cost me 5 years of, let's say, austerity. Never really had any financial problems during this time, but I also wasn't comfortable applying for loan to buy a house.
I don't want to offer any advice, just share a personal story which might be relevant.
As a counterpoint I would just point out that 6 years ago was a fine time to do this while now is a uniquely bad time. As someone who took gap year that that happened to end +/- 2 weeks from the start of the 07 global financial crisis, I'd be cautious about doing it now. My 1 year gap with a healthy brokerage account turned into credit card debt, moving back in with my parents, and a 3 year gap(half unemployed half very much underemployed working an internship with 4 years industry experience). It all worked out in the end, but it took 3 years to recover to the point I was at right out of university. So just keep in mind that you're like 6 weeks into a year or so stretch of what will likely be the best investment returns and the worst job prospects of the decade. And by worst job prospects, I mean, forget software development, I found out from a friend that one of many places I failed to get a job as a cashier was because they had apparently laid off a bunch of the cashiers and told the accountants/white collar staff to start working cash registers so they could justify not laying them off too.
I did something very similar, with a very similar pattern of stressing myself into inaction, though my combination of savings and freelance gigs only lasted me about 9 months. I'd hoped I would be free to the winds for the rest of my days, and it... didn't quite turn out like that, to say the least.
Still, I'm glad I did it. Because a) I hated the job I'd quit and was much happier with the one I ended up finding afterward, and b) it answered questions for me about what I did and didn't want to do with my life. Now I don't have to wonder: I know I don't want to freelance.
At first I thought I was going to do freelance work, but the longer I didn't start doing that the more I didn't want to do it. So after a year or so of playing with new tech and starting several personal projects which didn't turn into viable businesses, I began making some money with a website.
Because that profitable website and others I built afterwards weren't actually that profitable, 2 years after I quit, I had to do some freelance work to not run out of money. I had to do 3 years of small freelance gigs while growing an online business. So for me it was 5 years before I could pay myself without having to sell my services.
Not knowing from the beginning what I really wanted to do cost me 5 years of, let's say, austerity. Never really had any financial problems during this time, but I also wasn't comfortable applying for loan to buy a house.
I don't want to offer any advice, just share a personal story which might be relevant.