Archive
14 essays since January 2026.
2026
- I Wonder What Happens Now
Two years of head-down execution ended in a moment of looking up — and a slow recognition of what curiosity actually is once the good outcomes have stopped being available.
- Pouring Concrete
The post-WWII order is crumbling and small countries need to respond — but the hardest part isn't knowing what to do, it's that the problem demands exactly the kind of sustained, boring, comprehensive investment that democratic systems are worst at.
- Same Story, Faster Clock
Organizational ecology has spent decades documenting how industries are born, shake out, and consolidate — and the AI industry is following the script, with a few structural twists worth naming.
- Against Prescription
A course on how companies actually live and die made it impossible to sell the fiction that managers control the outcome — and quietly redirected a career.
- Accidental Complexity
Political systems accumulate complexity the way codebases accumulate technical debt. The answer isn't to tear them down or keep piling on. It's to refactor.
- Holding the Whole
AI dissolves accidental complexity at speed, but essential complexity — the question of whether it all adds up to something good — remains stubbornly human.
- The Architect's Exit
Kissinger defined a revolutionary power as one that rejects the legitimacy of the order it inhabits — then spent his career building America's. What happens when his framework fits its own architect?
- Soft Landings
I spent almost two decades loyal to one airline alliance — then the program changed its rules, and I started gliding away so quietly they'll never know I left.
- Staying in the Water
What building a bootstrapped company actually feels like after nearly a decade — not the VC default, not the indie hacker fantasy, but the uncomfortable middle where most of the building happens.
- Blast Radius
AI can reproduce substantial software systems. The moat against substitution scales with the blast radius of failure — but the line between what's safe and what's vulnerable keeps moving.
- The Absorption Gap
Four scenarios for how AI gets absorbed into the real world — and why all four are happening at once.
- Writing With Machines
I've always used writing to think. This time I'm using AI to write — not to produce text faster, but to think harder.
- Collapsing Cycles
Cycles are getting shorter everywhere — in careers, in technology, in how organizations work. A decades-old Marine Corps doctrine saw it first, and its insights about coordination under pressure feel uncomfortably relevant to building software with AI.
- The Perpetual Gale
The disruptions have started to overlap. If the world feels like it's accelerating, it probably is.