I really like the "culture matters" and "look stupid" posts. I've been allowing myself to look stupid since I was a kid in school. Dan is humble (frequently saying things such as "If an idiot like me can [do X]"), but I think this strategy requires a certain degree of intellectual security. For me the logic isn't just "this question may sound stupid but the knowledge gained outweighs that". It's also "this question may sound stupid but anyone who thinks I'm dumb is wrong".
I do not know how real-world accurate it is, but I enjoy the p95 post. For a huge number of skills in my life, I got to an acceptable level of performance, and then more or less never developed it.
