I disagree. Strongly.
Following your dreams, not working too much, spending time with family and friends, saying what you think, and being happy, might belong at the top of Paul Graham's todo list. He's already succeeded at what most people struggle at: making a living. He may have forgotten that getting by is hard.
What's so wrong about being a "cog in a machine"? Large organizations exist partly because scale and specialization are useful. People aren't "cogs" out of perversity, but practicality. Sometimes your comparative advantage is in being a good cog. And sometimes being a good cog is admirable. Example: surgeons who specialize in one and only one procedure, doing it exactly the same way every time, have a low failure rate. They save more lives that way. Are they creative? Nope. They follow somebody else's rules. They make themselves as mechanical, as repetitive, as possible. And the guy on the operating table lives.
Paul Graham is in a very unusual profession, where risk-taking is much more of an ideal than it is anywhere else. Also notice that he makes money off of telling other people to take risks. The more people decide to be entrepreneurs, the wider a pool he has to draw from. "Follow your dreams" is a useful meme for people like that; if a hundred people follow their dreams and fail and ruin their lives, PG never hears about it, but if one person follows his dreams and becomes a billionaire, PG might get a share. This isn't meant to vilify the guy; there's nothing wrong with making a living by inspiring people. And I'm sure he would say that he's fighting dangerous opposing memes against ever taking risks. I just think you can't take posts like this at face value.