Style / voice is something you can’t really pinpoint. It tends to happen like this: you combine a bunch of idiosyncratic things you like, and ... something happens between those things. You have your interests, you have your sense of humor, you have your grammatical tics, etc: the more you just incorporate all of the stuff that you love or that jus... See more

I think about it like this: I want to have a balance between pushing myself hard so I learn new things, but I also want to finish stuff because there are certain things you can only learn by finishing. Deadlines is the tool that lets you find the balance. Say, “I’m going to write the best piece I can in 20 hrs” and then you adjust how high you aim ... See more

This, however, is not an excuse not to be disciplined in your thinking. But it is mostly a separate process: spend serious time reading, taking notes, learning, challanging yourself. But when writing: let that go, and rely on the brain power that you have accumulated. A good essay is an interesting mind wrestling with a problem in somewhat real tim... See more

Write from emotion. This goes back to the chat messages: the aliveness there usually comes from talking to someone you really like and wanting to resonate with them, or wanting to amuse them. This creates an emotional surge in the writing. When you write from your head too much it tends to have less style.

Here is a classic pattern: you try really hard to do something GOOD, then you fail, or you make something silly. And it is the failures that people love, or the thing that was just a silly thing. So try to set yourself up to failure, to not doing the thing that is right, but the thing that just sort of happens when you are not trying.

Don’t aim to high when you begin. Maybe just do 500 word pieces, and do them with a simple format: problem, solution; an observation; explain something you’ve been wrong about. Done.