May 2026 — OODA loops, Billy Waugh, and the people who will actually thrive with AI
I have a 2003 Lexus LX470, the fancier version of the indomitable Land Cruiser. I love her. 203,000 miles in, still unstoppable. She has a strong motor, but she’s pretty long in the tooth - there are limits now. Rattles a bit here and there, she can’t accelerate the way she used to, and above 75mph, she’s a little less... smooth. She’s at her best when she’s within herself. Because of all that, I notice I’ve gradually stopped trying to push her. It’s clear she isn’t meant for the daily grind anymore. But her engine still is.
And that image has been sitting with me. Nearly three months into Albers, I’ve got good work, a clear mission, and a team that’s pulling together. Yet something about this season still feels unresolved. Maybe it’s an engine that was running hard with Eden Green, and now is, in some ways, running quite differently, with a mental and emotional chassis that is temporarily… unsmooth. It’s not a problem; indeed, I’m thankful for this stage. It’s more like a threshold I’m standing on, still learning the shape of what’s on the other side.
What I’ve Been Reading
Billy Waugh — Hunt for the Jackal. The memoir of one of the most decorated special operations soldiers in American history — Green Beret, CIA paramilitary, still running ops at 71. The missions are extraordinary. What stayed with me wasn’t the missions. The book has no family, no friends — only colleagues. It left me sitting with a question I keep turning over: you can be at the highest levels, still in theater until the very end, and never have asked to what end?
Seth Jones — The American Edge. A rigorous case for where America’s strategic advantages actually lie in the current competition. The WWII industrial mobilization chapters are the most clarifying — a civilization that oriented fast and moved with extraordinary speed when the moment required it. What frustrates me now: we haven’t done the same kind of orientation work on the China threat. The public awareness isn’t there. The bureaucratic urgency is lagging further. We know what surge looks like historically. We seem to have forgotten how to want it.
Ben Sasse, interviewed by Ross Douthat (podcast, ~90 min, worth it) · Sasse is publicly dying, stage 4 pancreatic cancer plus other companions, yet he is so at ease with himself, and has ever more clarity on life, and culture. There is such an intense richness to the interview. My friend Brent Beshore wrote a masterful piece on Sasse, and I would belabor the point, and quite poorly. However, during the interview, I honed in on his commentary on AI tools and the coming divide: “For a small number of people with lots of intentionality, lots of habits and fit communities of accountability and Sabbaths, these tools are probably going to be pretty great. For the majority of people, I think they’re going to be disastrous.” The word that stayed with me was Sabbaths — not as a religious practice but as structural resistance to compression. Intentionality isn’t a mindset. It’s a set of practices you build before you need them. Full interview here at NYTimes. Whether you have a faith or not, it’s worth the listen.
What I’m Thinking About
We all have OODA loops — Observe, Orient, Decide, Act. Col. John Boyd developed the framework for air combat, but it maps to almost everything. Most of us in high-velocity careers have quietly compressed our loops: we spend our cognitive energy almost entirely in Decide and Act, treating observation and orientation as a tax on productivity rather than the work that makes everything downstream worth doing.
This season has forced me back into the first two phases. What I’m finding is that Orientation is Boyd’s most complex node — it’s where mental models actually get rebuilt, where previous experience, new data, and unsettled questions all have to be reconciled before the next move. And the reason this particular orientation feels unfamiliar, even with the reps I have from previous transitions: I’m navigating a professional loop and a life-stage transition simultaneously, for the first time at the same time. Neither can resolve cleanly until the other makes progress. I don’t have a tidy conclusion. I’m still in it.
The Sub-Plot
High performers don’t fear action. They fear observation without action — because from the outside, it looks like nothing is happening. The Observe and Orient phases are invisible, which makes them almost intolerable for people wired to move.
But the quality of every Decide and Act you’ll ever make is downstream of how well you oriented. Waugh kept moving until he was 71. The to what end? question is an Orientation question — and the book suggests he may have deferred it indefinitely. The defense industrial base has a version of the same problem: the capacity for surge exists in our history, we’ve proved it, but we haven’t done the Orientation work to want it urgently enough. And Sasse’s divide is the individual version of all of this. The people who thrive with these tools will be the ones who have maintained the capacity to Observe and Orient in a world designed to make that impossible. Everyone else will just Decide and Act faster, on older and older mental models.
What are you orienting on right now? And if you’ve read anything that’s genuinely sharpened your thinking on the China competition — send it my way.
-eddy-
If you feel like you want more of these, throw that email in there.