Why I retired from speaking
This is a copy of the Searls of Wisdom newsletter
delivered to subscribers on October 12, 2024.
Hey everyone, have a good September?
Apologies, as most of my top-of-mind thoughts are hurricane-adjacent as I write this:
- That we decided to escape the storm by driving from Orlando to Savannah on Wednesday morning
- That I spent Wednesday night tossing and turning in bed after Milton made landfall, wondering whether I'd be more upset if there was significant damage to the house (and with it, the hassle of months of insurance claims and repairs) or if there was zero impact at all (rendering my 10 hours in the car an unnecessary hedge)
- That, in college, I rented a house on Milton Street we all called "The Milton", and how disappointed I am that none of Orlando's local news affiliates thought to call me to discuss this fascinating human interest story
- That our house is absolutely fine. Didn't even lose power. And my predominant emotional reaction is, predictably, to feel like the drive was a waste of time
Anyway, that's October stuff. And I'm not here to talk about October stuff, because Searls of Wisdom is a publication that happens in arrears. It takes a full month for these insights to coalesce and maturate in the nacre of my self-indulged mind.
So, let's talk about September stuff.
The one thing I'll remember about September 2024 is that it was the month I gave my final conference presentation. After 15 years of speaking at user groups and software conferences, I've decided to hang up the presenter remote. End of an era.
Here's a pic of me and my friends Aaron and Eileen at the RailsConf: World Edition afterparty:

It's been strange developing so many impactful friendships over dozens of seasonal pseudo-vacations sprinkled sporadically throughout my adult life. I've rarely ever visited these friends where they live, or met their families, or seen how they operate outside the predictable plot beats of a conference event. Each relationship a vignette of awkward run-ins at baggage claim and hotel lobbies. Strained catch-ups at noisy speaker dinners and sponsor parties. Warm greetings crossing paths in convention center hallways. Hushed critiques shared from the back of other people's sessions.
I can happily live without attending another conference. But will that mean living without most of these friendships, too?
Yeah, probably.
Below, I'm going to discuss my decision to announce my retirement from public speaking, how people reacted to it, and what the resulting dissonance can tell us about weighing loss aversion against opportunity cost.
Content warning: more content…