Hackers and Painters: An unbashed recommendation
The book then takes a more technical turn. One of the best essays here is about how web-based applications will change the rules of the game, load it in favour of innovators rather than the big companies and why they would make software engineering easier. Graham is quite clearly a big fan of Lisp and describes its use in his startup ViaWeb and why it is the ideal programming language of choice. There are quite a few other interesting topics he touches upon.
If that doesn't sound impressive, you can be rest assured that coming from a practitioner who has seen it all, it sounds absolutely natural, with a sense of deja vu. His writing is witty and very lucid. The arguments are well reasoned and the chain of thought is well presented. And there are quite a number of smart one-liners you can smile at. This is a case of text book essay writing (if I may use such a term). Highly recommended.
You can find many of these essays and more on Paul Graham's site.