There's a lot of good stuff in Paul Graham's Hackers and Painters. A fast [readable] romp through hacking, sketching, day jobs, open source and user empathy.
On a different note. In some hotel bar in San Francisco, I was lamenting the lack of a badge of honour for geeks. And not like gadgetry or clothing but a specific tool essential to the job that takes knowledge to use properly: a harmonica, a tuning fork [a code fork...]: something that could be worn in a battered leather pouch on a belt around the waist, whipped out, unfolded and it's an ssh window in thin air -- reach in and fiddle around with the machinery.
- So you want something to keep hacking exclusive? said Cory (I paraphrase). And yes okay, that's what I was saying and it's a really bad thing.
But there's another way of looking at it. The tools for expert users needn't be the same as the tools for novice users. Or at least, for the same level of cognitive friction, the tool can mesh better with the way the expert user thinks (I find BBEdit grows well with me like that). The point being, you're only a first-time user once.