Having read Steve's Post on 10 reasons to never get a job - I think the reason he's against jobs is
Confirmation bias - Steve wants to believe he is happier not having a job. The reason I think this is that the tone of the article is quite negative (even the title is negative) and the arguments don't really stack up (self employed people earn 24/7? does that include plumbers?). I'm glad that Steve writes a blog so I can read it - and it's great that he makes a wedge of cash too, especially since I get his wisdom for free.
Here's 10 reasons to work for a living (just for a laugh):
1) If I screw up and lose the company $1m, the most I can lose is a paycheck.
2) Most business startups fail in the first year.
3) I'm in a social environment - I meet new people every day
4) I'm learning from how other people work, and from other people's ideas.
5) I'm out of my comfort zone - my manager pushes me to try new things
6) It gets me out of the house
7) I don't have to care about my work on the weekends - it's not my business, it's someone else's.
8) If I get sick, I get paid when I'm sick. If I die or become disabled, there's insurance to help us cope.
9) I'm part of a team, we work together - there's no stars or primadonnas, we get things done.
10) There are more important things in life than work.