It’s nearly 4am here. I woke up with mild heartburn. Before I could go back to sleep I started thinking about this newsletter. Eventually I decided to get up and write my thoughts if I was going to be awake anyway.
Since last issue, I’ve been thinking about what it means to write well, what it would mean for me to write well.
I think the fact that humanity has recently invented a technology that can do all the writing we’d ever want on command has forced the question. Like the kid in math class who asks why they should learn long division when a calculator can do it just as well and faster.
My last issue, in which I admitted to experimenting with using AI to coach my writing, was nearly a month ago. I usually publish weekly. My absence is partially due to recent work deadlines, but also to becoming anxious whenever I think about allowing an LLM to socratically chisel my writing into a polished caricature of my thoughts with little room for uncertainty and ambivalence.
I still believe that the purpose of writing is to connect human with human, author with reader, mind with mind. And, if that’s the case, to write well is to pour myself into the page.
The issue is that often I’m not sure I want to do that. I’m an overweight divorcé with questionable hygiene practices who until recently rarely left his apartment. Why should I voluntarily poor myself onto the internet for all to see?
So I’ve rushed through it like an unpleasant medicine. Roughly thirty minutes from start to publish, too little time to overthink things, to get in my own way.
I thought that an AI writing coach would allow me to step beyond that. It would add structure that would improve my writing beyond publishing messy first drafts.
Unfortunately, the result was a piece of writing that had less of me in it than a messy first draft would, perhaps because I’m so messy and unfinished.
I want to respect you, the reader. But at this point it feels more disrespectful to give you something that has the messy parts of me patched out than it does to send you a first draft. Neither is ideal. But at least a first draft still has the potential to be authentic connection.
I guess this means, for now, I’m going back to not using an AI writing coach. Perhaps I’ll try it again in the future, create a new Claude skill, experiment with a new process. But at least for this issue, for better or worse, an unfinished draft will have to do.