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From The Age of the Essay:

Paul Graham

  • An essay begins with a question. You notice a door that’s ajar, and you open it and walk in to see what’s inside.
  • Surprise the reader by telling them something they always knew deep inside but didn’t bother to do the work to make it conscious.
  • Collect surprises. It’s a trainable skill. The more anomalies you’ve seen, the more easily you’ll notice new ones.
  • Pay attention to things you’re not supposed to. If you’re curious about something, trust your instincts. Don’t believe what you’re supposed to.
  • Expressing ideas helps to form them. In a real essay you’re thinking out loud.
  • Writing something that other people will read forces you to think well.
  • Don’t plan. From paragraph to paragraph let the ideas take their course. Real thought is full of false starts. An essay is a cleaned-up train of thought.
  • Of all the places to go next, choose the most interesting.
  • Aim for maximum surprise – things you didn’t know that contradict things you thought you knew. What surprises you?
  • Ask ‘why’ about things that feel off. That’s where fruitful material is.
  • Read it out loud and fix everything that doesn’t sound like conversation.
  • Ask reviewers for two things: which parts bore them, and which seem unconvincing.
  • Cut the boring bits.
  • Make unconvincing bits more clear, or change what you’re saying if you’re wrong.

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