2026
Where Software is Going
AI made generating code cheap. The disciplines that used to be optional, the harness and knowing what good looks like, are now the whole game.
Things I’m building, teams I’m leading, habits I’m creating, and hobbies I enjoy. I’ll try for weekly — and when I don’t, I’ll let you know.
AI made generating code cheap. The disciplines that used to be optional, the harness and knowing what good looks like, are now the whole game.
How Nassim Taleb's Antifragile changed the way I think about money and risk, and the barbell strategy I'm now applying to everything from the car I bought to the way I invest.
How I used Claude to find my values, why naming them gave me permission to stop caring about everything, and the site I built so you can do the same.
How I used Claude to structure a talk around Patrick Winston's 'How to Speak', and why the method, not the model, is what made it land.
Why I dropped spec-driven development for ShapeUp, and how splitting decision clarity in two changed how we ship.
How I landed on Sunsama after Claude and Morgen didn't stick, and why the daily plan and shutdown ritual mattered more than the tool.
How I used AI to actually apply a book to my life, and the public posture that fell out of it.
The four fundamental team types from Team Topologies, stream-aligned, enabling, complicated-subsystem, and platform, and how to design team boundaries deliberately instead of reactively.
The three modes of team interaction from Team Topologies, collaboration, X-as-a-Service, and facilitating, and the anti-patterns that emerge when team interactions aren't consciously designed.
A summary of Jonathan Rauch's case for the reality-based community, the norms that keep truth-seeking honest, and why epistemic chaos is the modern threat.
Why team structure and dynamics matter more than individual brilliance, and how small, stable, long-lived teams with clear ownership produce better software.
Infrastructure should support innovation, not be it. The case for boring technology, vendor-supported solutions, and protecting the innovation budget for customer-facing work.
Why centring the release process around a build artifact gets you speed, simplicity, and traceability, and why infrastructure delivery is a different beast that deserves its own pipeline.