I have trouble believing just on his word alone that StevePavlina.com generates $40000/month. It's possible, but I'd have to see some evidence.

... especially after calling most of his readers morons for believing that a job is the safest way to support themselves. And then there is the:

"If you find this site helpful, please leave a donation for Steve so you can enjoy the spirit of giving too."

which just seems crazy after what he said, but maybe he knows his audience well.

Once you get past the "motivational speak", there are some good points that he makes. We truly are conditioned to believe that getting a job is the best way to provide for your family. I grew up in a restaurant, so the principle of working hard for what you earn was instilled in me at an early age. Now, thanks mostly to pg's essays, I realize that the best way to provide is to work smart - start a company, give it your all for a few years, and let it generate income as a return for the wealth I've created.

Jobs in academia seem to have some advantages, particularly with respect to freedom. But that really depends on where you end up: http://www.lambdassociates.org/blog/decline.htm. Moreover, your views about what constitutes interesting research in computing may differ from those of the majority: http://weblog.fortnow.com/2006/07/science-and-art-of-computation.html.