I think there's plenty of room in the world for people of both mindsets - those who seek employment and those who wish to be self employed.
I think Steve's point of view aims to get people with latent potential and talents (the "smart people" he aims his content at) out of the conformity mindset, there are many square pegs who try to stick themselves in round holes because it seems like an easy option, but these people may be happier and more successful running their own business or being a freelancer.
However, there are people who can happily be employees, I'm one of them and the reasons I'm happy with this arrangement is because I think of myself like a self-employed person, offering my services to an organisation I choose to work for. I also see that one day I could do something more entrepreneurial (and already do a little on the side), but for now I'm happy honing my skills as an employee and being of service that way. I guess my point is that I feel it is my conscious choice rather than something I "have to do to pay the bills".
Another factor that helps is that my DH runs his own business, so as a couple we get the benefits of both lifestyles (he gets to sleep late and work in his PJs, I get to go out, interact with people and appreciate homelife at the end of the day!).
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