It’s always about TONE. If the tone is not there , then there’s no writing. And to get anything done, I need tone and a sense of outline. And the outline is much easier to get to the tone. I don’t have the heart to try to make an outline until I believe there is a piece of writing to be done and the piece of writing will exist as soon as I believe there is a tone to write it in.
A piece of writing is not interesting or worth doing if there is not some personal risks, if it is not dangerous in some fashion, whether your’re exposing some part of yourself you’d rather not talk about or whether it be being sincere about something that would be much comfortable to be ironic about and vice versa. If you’re being sarcastic or ironic about something that people people take seriously.
There can be some contempt risks. You don’t want to be seen writing such a thing or literally something somewhat obscene to do for journalists. But particularly if there is some elements of psychological risks, there is a discomfort. The first thing you have to know is: “Can I find the way to write about this uncomfortable thing that will not make people uncomfortable when they read it. And that distance is always navigated by way of a piece’s tone; do you like how you sound as you write about it or do you sound like a pompous asshole? And you cannot immediately know that but as soon as you start hearing, “Oh this I could read aloud and it would not kill me and yet people might simultaneously enjoy but also be slightly uncomfortable about it. That is where I wanna be.
And as you start hearing that by reading some paragraphs that you see,”Ok, I can read the whole thing in that voice and that will be OK”. At this point it is safe to make an outline and go on.
So that’s my process.” (As transcribed from a BIG THINK interview)