From Myke Hurley’s “State of the Workflow” series on the Cortex podcast (Overcast, Apple Podcasts):

Myke interviews John Gruber of Daring Fireball. They take a deep-dive into how John’s writing takes shape – from capturing ideas and drafting articles to the meticulous editing behind his influential work.

This was a fantastic interview. Gruber started writing at Daring Fireball in 2002, about a year after I started at Apple, and I’ve been reading him since day 1. He’s very prolific and very influential within the Apple community. I’ve always been curious about his writing process, which allows him to churn out piece after interesting piece—but especially so now, early in my second year of public writing as I find my voice, a rhythm, and an audience.

It was revelatory to hear that several of my challenges, from procrastination to word obsession, mirror his own. I was especially chuffed to learn that our writing processes are similar. Asked “Do you agonize over word choice?”, Gruber answers:

I have always, I mean, literally since childhood, always tried to write my final draft right off the bat. Especially the longer the article, the more editing I do for myself. But I can’t bring myself to write other than thinking that I’m just going to start typing with the first word and get to the final word and just hit publish.

Like, the canonical ideal for me would be to not even proofread and just write what I think it’s going to be and hit return. So I, at every step, every single word of the way, am trying to pick the right word. And so yes, I obsess over word choice.

This is almost exactly how I write—and have for as long as I can recall. My goal (rarely achieved): Write straight through, as perfectly as possible, and publish. Start with a thesis—often just an emotional reaction—and write until I’ve exhausted the idea I’m pursuing, agonizing over each word, sentence, and paragraph as I go. Allow the act of writing to determine what needs to be written—How can I know what I think until I see what I say? I’ve rarely had success using outlines or bullet points to write, because the words I want to write I can only find by writing them. Bits and bobs become full sentences, which turn into complete paragraphs, and suddenly I’m not outlining, I’m writing. As Gruber says:

Don’t prepare to do the thing, just do it. I just need to sit down and start writing. And anything that feels like I’m working on the article, if I’m working on the article at all, I might as well just start writing it.

“Writing is thinking on paper.”