I've left this thread alone for a while because I have a lot to say on the subject, and don't know if I can be brief.
I, too, contemplate quitting the day job. I went to college and earned a psychology degree. I planned to use it to teach grade school, believe it or not. I took my qualifying exams (and did very well), but then, for some reason, never applied for the teaching program. I basically left college without direction. As a result, I ended up working for the family business, something I swore I would never do.
Now here I am fifteen years later, and I'm still working for the family business. It has its upsides, of course, including a tremendous amount of freedom. Get Rich Slowly would not exist if I had been working at a real job. I wouldn't have had the free time. And it's good to work with my brother and cousin. But I do not enjoy the work. I especially loathe the constant interruption by telephone. I'm the kind of guy who gets wrapped up in his thoughts, all daydream-y and stuff, and the constant phone calls (which I have to answer) break my concentration. It's part of the job, obviously, so I can't complain. But I don't enjoy it.
Now, though, it's looking as if I could actually support myself on income from my various web sites. I have a plan in place to gradually remove myself from the business. It's a scary prospect, obviously, but one that excites me, too. It would allow me to devote more time to producing quality content for all my sites, and give me time to write a book! :0