darnoc
My job is kinda specialized, it has to do more with statistical programming and mathematical modeling than the coding that most people on HN do, so I guess that helps when it comes to trying to go it alone. To the extent that I'm qualified to dispense advice it would be to develop a specialized skill that your average competent hacker doesn't have, particularly if it involves a lot of math--a lot of good coders I come across know surprisingly little math. Most of the people I know who are successful consultants have such a background.
So I work 20hrs a week consulting and spend the rest of my day reading, studying (I'm getting a masters in my spare time), cooking or playing music. There are definitely days when I am envious at my friends who work in tech, what with their fat 401ks and rockin health care and 4x income. But usually not. I'm in way better shape, have read 10x as many books in the past year, traveled more, etc. Most importantly, every time we hang out I just sense that they are unhappy and bored.
I realize most of the people reading this are going to be a lot more like aforementioned friends than like me so I hope this doesn't come off as insulting. When I think of my friends I really wonder what makes it worthwhile for them--but of course I could never ask that without sounding like a jerk. So if anyone is reading this I'd love to hear. Is it just the $$? Because I feel like you need so much less of that than you think to be really happy.