Health insurance is a huge factor for sure - but I actually wrote an article a while back about how I was able to overcome it (finding a semi-affordable one isn't impossible and it takes 1-2 freelance gigs to make back the money) - most people don't think of it that way and become too afraid to pay for insurance themselves. It would be a lot better if we have government support for healthcare even as independent workers, of course.

The point I was making in the article is - you can find financial support in a way that is conduicive to you dedicating almost everything you have to your business. People do it differently - some get second jobs. Personally I thrive in teaching and it provides great flexibility and support. But if we always have a "if this doesn't work out, I can go back to what I was doing before" mindset, we subsconsciously won't really give 100% of effort that's needed to make our ventures successful.