I don't write as a living, but I do work in Hollywood. I've never had a traditional day job, but when I first got started I had day-job-gigs I didn't want to be spending all my time on, and the way I realized I didn't need them anymore was that I ran out of time to do them. It's a metric that worked for me!
I do pay through the nose for my health insurance though, and it's been a nightmare. And judging from the number of views a blog post of mine about the difficulties of getting health insurance as a freelancer got, a lot of people feel the same way. For some people it's not bad, but in the U.S. it's heavily dependent on the state you live in and the condition of your individual health. So do take it into consideration.
I do pay through the nose for my health insurance though, and it's been a nightmare. And judging from the number of views a blog post of mine about the difficulties of getting health insurance as a freelancer got, a lot of people feel the same way. For some people it's not bad, but in the U.S. it's heavily dependent on the state you live in and the condition of your individual health. So do take it into consideration.