Three essays that I read at least once a year:
The SCUM (Society for Cutting Up Men) Manifesto by Valerie Solanas: Oh come on its sort of so crazy its true. Or so crazy it’s kind of really funny.
Why Nerds are Unpopular by Paul Graham: Uh pretty much sums up my life, philosophy and general discontent with Education. I would re-type this essay and call it my own–that is how much I suspect Mr. Graham has plagiarized my secret thoughts. (Note that both Solanas and Graham would be in strange agreement re: the artificial boundaries of child/teen/adult hood)
How to be Creative by Hugh McLeod: I read this when I am know I am starting to make too many excuses. Particularly excuses to spend too much money on art supplies. Although I think I really could use a power drill.