Simon Willison’s Weblog

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14th September 2026

Comment My comment on What blog posts influenced your thinking the most? — Lobste.rs

An early Joel Spolsky one for me was The Law of Leaky Abstractions. I read that near the start of my career and it's encouraged me to always be looking for improved understanding of the layers under where I'm working, just in case one of those abstractions leaks.

A more recent one, from 2018, is Migrations: the sole scalable fix to tech debt by Will Larson. I absolutely love his idea that migrations (e.g. replacing one service with a new one, or switching database engines, or whatever) are part and parcel of software engineering and are a skill that you should invest in and get good at, not avoid or treat as special one-offs.

The Engineer/Manager Pendulum by Charity Majors was hugely influential for me. I was stuck in engineering management and worried that if I switched back to being an "Individual Contributor" (ugh I hate that term) I'd damage my career. Charity gave me permission to make the switch by pointing out that many of the most successful software developers pendulum from one track to the other multiple times over their career, and doing so makes you better at both sides.

This is a beat by Simon Willison, posted on 14th September 2026.

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