How I Did It by Jonathan Coulton. He describes how he went from messing about to superstar musician!

I love how his article describes the point he figures out he is good and that people want to listen, and not just to be nice.

Remember, all this was before I quit my day job writing software, and I think that’s an important thing to note - you can get a lot done even while you have a job. Career transitions are tricky things, and the more you can get established in the new one before you leave the old one, the easier it will be.

But then I did quit the day job. I’ve talked about this a lot in interviews, and yes, it felt very scary and in a lot of ways it felt like a mistake. And I wasn’t sure how or even if I was going to be able to make a living this way, but for whatever reason I felt like there wasn’t ever going to be an easier time to do it. Luckily my wife was onboard with the plan (or rather, non-plan), even though she was at least as doubtful as I was about it being a good idea. But we knew that at least for a while we could stay alive with just her income - worst case scenario, I could always get another job.