Paul Graham is both smart and wise. On the futility of seeking wisdom qua wisdom:
People seeking some single thing called “wisdom” have been fooled by grammar. Wisdom is just knowing the right thing to do, and there are a hundred and one different qualities that help in that. Some, like selflessness, might come from meditating in an empty room, and others, like a knowledge of human nature, might come from going to drunken parties.
Perhaps realizing this will help dispel the cloud of semi-sacred mystery that surrounds wisdom in so many people’s eyes. The mystery comes mostly from looking for something that doesn’t exist.
On the discontent of the over-achiever:
To me it was a relief just to realize it might be ok to be discontented. The idea that a successful person should be happy has thousands of years of momentum behind it. If I was any good, why didn’t I have the easy confidence winners are supposed to have? But that, I now believe, is like a runner asking “If I’m such a good athlete, why do I feel so tired?” Good runners still get tired; they just get tired at higher speeds.