How I wrote "Looking for Alice"
Writer's Diary
Alexander Calder’s workshop
Something I found frustrating when learning how to write was that writing advice tends to be very low resolution. You have someone looking back on their experience writing for decades and they sum it up by saying, oh, well, don’t use adverbs.
I wish there were more detailed accounts of the decisions writers make when they struggle with a particular piece.
And since my general rule of thumb when writing this Substack is “write stuff that I would have loved to read a year ago”, I figured I should do that. A case study of how I write an essay. I’ll do Looking for Alice, an essay about not dating, one of the better I’ve written.
I warn you: this is going to be over-the-top nerdery. It is not for normal human beings. But if you like writing, or enjoy seeing someone analyze their craft, maybe this will be fun and useful.
December 28, 2022
I wrote Looking for Alice at what for me is a rapid pace—I had the idea on the evening of the 28th of December, 2022, and published it on January 17th, 2023. Normally, it takes me several months of revisions before a piece comes together.
This is where the idea came from.
I was on a Zoom call with Steve Krouse, an internet friend who lives in Brooklyn and runs a startup called val.town. We were having a normal internet friend conversation about Seymour Papert and end-user programming and such stuff, when Steve said, “This might be a strange question, but I wonder if you have any thoughts about dating.” He was under the impression that I am happily married (correct) and wanted to know how I did that.
There is a classic writing tip that says you should imagine the person you are writing for—it is even better when that person is asking you questions. As Steve asked questions, I noticed it was a lot of fun telling him about the experiences I had when I met my wife, Johanna. And it seemed he liked the advice I gave.
Maybe I should write it down? I thought.
No, that would be ridiculous—a piece about love.
But maybe?
Substack saves a version history of every post. Looking at the time stamps, it seems like I made a draft right after the call. Then for the next four hours, I opened it several times to jut down ideas in case I wanted to write the piece, which I surely shouldn’t do.
I remember that I was working on a long series of posts (still not finished) about designing software to facilitate social learning, which felt like an IMPORTANT topic. But the important stuff was a slog, so I kept procrastinating by sketching up ideas for the piece about not dating.
It should have been obvious that this was a good piece. When something forces you to write even though you can’t justify it and even feel a little ashamed, it must have some inherent energy to be able to push past your defenses. Pieces you don’t feel awkward about (when you have an idea and go, “Ah, this is great, people will like this!”)—those ideas don’t need to be as good to get themselves written. My resistance is a filter, and the ideas that pass through it are my best pieces.
By midnight (when I really should have been asleep for several hours), the draft looked like this footnote1. It is not good (”The first draft of anything is shit”, as Hemingway had it) but if you’ve read the essay you recognize that a few of the things that made it into the finished piece have already appeared on the first night.