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Recommended reading

Things worth your time

Books, websites, and individual pieces grouped by the questions they helped me think through.

A

Making things that hold up

Craft, systems, and the stubborn details between them.

book
The Timeless Way of BuildingChristopher Alexander
Note

A book about buildings that keeps turning into a book about software, teams, and the conditions that let good work happen.

website
Simon Willison’s Weblogsimonwillison.net
  • Things we learned about LLMs in 2024The useful annual inventory.
  • Here’s how I use LLMs to help me write codeSpecific habits, not declarations.
  • Notes on using LLMs for codeTwo useful modes for working with the tools.
Note

One of the few places where the daily practice of building with AI is documented in public, including the awkward bits.

B

Institutions in the wild

What organizations can see—and what their abstractions hide.

website
Works in Progressworksinprogress.co
Note

The whole publication is the recommendation: ambitious explanations of why the built world works the way it does.

book
Seeing Like a StateJames C. Scott
Note

A durable warning about the distance between a clean model and the inconvenient, local knowledge it leaves out.

C

Staff+

Growing scope and influence without leaving technical work behind.

book
Staff Engineer: Leadership Beyond the Management TrackWill Larson
Note

A useful vocabulary for the work, influence, and growth of senior individual contributors—without treating management as the only path forward.

© 2026 Matt Ouille.
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