Writing Advice

  1. Write because you actually have something to say. “There are two types of writers, Schopenhauer once observed, those who write because they have something they have to say and those who write for the sake of writing.”
  2. Be helpful. It’s amazing how much writing is blatantly not helpful. Telling me something I already know isn’t helpful. Telling me something random and unimportant isn’t helpful. Giving me your vote of confidence on something that has already been said many times isn’t usually helpful (unless it’s a controversial topic and I already know you and value your opinion). Taking something complicated and making it easy to understand is often helpful. Inspiring me is helpful. Making me laugh is helpful.
  3. Use the ADEPT method when explaining things. Analogy, diagram, example, plain english description, then technical description.
  4. Rewrite. A LOT. “The best writing is rewriting.” — E.B. White. I think it’s especially helpful to come back to something that you wrote weeks/months/years ago and rewrite it. It’s amazing how useful that fresh perspective is.
  5. Play devils advocate with yourself. How would you beat yourself in an argument?
  6. Ruthlessly eliminate what Just Doesn’t Matter. Readers are investing their time. Give them as good an ROI as possible. 300 page books that should have been 125 pages do not have a good ROI.
  7. Air-tight arguments aren’t always a good idea. They take a really long time. They can cause you to lose the forest for the trees. Unless it’s a legal document or an academic paper, the disadvantages of air-tight arguments probably outweigh the advantages.
  8. Treat writing like UX, and do user research. Don’t just get feedback, do user research. In the context of UX, people often think user research is unnecessary, time-consuming, and difficult. It’s not. I think the same applies to writing.
  9. Give yourself sufficiently big chunks of uninterrupted time to write.
  10. Write like you talk.
  11. Start with the concrete, then the abstract. It’s just so much easier to understand things this way. Humans are good at extrapolating from concrete examples. Abstract things without a context are confusing.
  12. Read good writing.
  13. If you can’t get going, tell a friend what you plan to write about, and then write about what you just told them.
  14. Be prepared to ditch the original plan. “Expect 80% of the ideas in an essay to happen after you start writing it, and 50% of those you start with to be wrong” — Paul Graham.
  15. Trust your gut. It isn’t random. It’s the result of information processing and accumulated experience. And it’s usually right.
  16. Take a few minutes to use decent typography and formatting.
  17. Don’t write. Communicate. Think about what writing is. It’s communication. If there’s a medium other than the written word that allows you to better get your point across… then use it! (Pictures, diagrams, videos, animations, GIFs, physical models, sound…)
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