Paul Graham departs from his usual programming bailiwick to ponder, in a rather meadnering fashion, writing essays. The key is to go back to the roots of the definition of "essay", which I take as simply attempting to work through your personal hurdles.
Graham's advice is actually relevant for many creative endeavors in life besides writing. Pursue surprises. Work out loud, but be ready to revise your thinking. Start small to grow something big.
Work out loud. I sort of like that term.