http://khanism.org/perspective/minimalism/
When that failed I had to get a real job again, but got sick of it after a year and a half:
http://penguindreams.org/blog/leaving-full-time-jobs/
Then I took off on the road again and eventually had to return to the full time job/life:
http://khanism.org/perspective/a-tale-of-two-journeys/
I did something. I failed .. well maybe not failed so much as just didn't find a way to sustain myself. But each time I hope I get a little better at it.
And yea ... at least I tried. One day I'll be dead. At least I got to see Singapore, feel the wind of New Zealand, ride through the deserts of Australia, do a radio poetry show on the 8am commute in Perth.
He made some bad decisions. We can see that in the retrospectiscope. I agree I had trouble reading it. But yea, respect for trying. He lost a ton of money? Well as long as he can save enough to pay for his kids' education, at least he has a story to tell and they can learn from him.
It's all relative. I can see the bad and see the good. You gotta try, or else you're just gonna die in your cube.