i was a salaried tenured teacher who had a guaranteed job for 30 years. I decided I would be happier wearing my pajamas and working from home on something computer-related.
My plan was to go back to school and move slowly, so I moved from teaching to positions within the school district where I could work with computers. First computer teacher, then adult instructor, then network admin for an entire school. I got the school district to pay for my computer certs (MSCE and comptias). I stocked up on office supplies to last me 5+ years. And then I worked at a university who paid for my MBA - working for the man still, but planning all along to be on my own eventually. I just didn't quit one day - I saved up contacts, supplies, ideas, etc for a few years first. Every time I installed an OS as a netadmin, I copied a disk for myself. Everytime I had to design something complex for the univ website, I kept a copy so I'd have that trick in my web design book down the road. Transition took 3 years total - MBA and an AS in computer networking included while learning new jobs.
So I guess in response to your situation is that I knew I could very well fail if I worked from home, so I tried to set things up so that I could come back, and my resume would be stronger for the change. 99 out of 100 people aren't right for being self-employed. If you are that 1%, and you can deal with that constant stress of "I gotta find work or I'm so screwed", then you'll
definitely end up making more money than you would for a boss. And you'll be able to train at 10 Am daily if you want
I'd say plan it out, get every possible advantage, copy every piece of software etc from your current job as possible, then give it a shot while you're young!