Simon Willison — 2026-05-11#

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Today’s dispatches heavily focus on the macro consequences of the “agentic era” on the software industry, exploring everything from how coding agents are forcing massive corporate restructurings at GitLab to the stark mathematical reality of AI-generated codebase maintenance debt.

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GitLab Act 2 · Source Simon unpacks GitLab’s recent workforce reduction and structural flattening, which reorganizes their R&D into roughly 60 independent, empowered teams tailored for the agentic era. He highlights GitLab’s Jevons-paradox-inspired outlook: as AI agents collapse the cost and time of producing software, the overall market demand for software—and the builders who make it—will radically multiply. However, Simon pragmatically notes that GitLab has a strong financial incentive to project this optimism, given a recent 50% drop in their stock price and a business model heavily reliant on growing seat-based licenses.

Simon Willison — 2026-06-04#

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Simon shares a fantastic piece from Charity Majors that articulates the current tug-of-war in engineering teams: the race to leverage AI capabilities versus the threat of unmaintainable, auto-generated code. It is a highly relevant read for any engineering leader struggling to balance the speed of AI-assisted development with the long-term health and comprehensibility of their systems.

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AI enthusiasts are in a race against time, AI skeptics are in a race against entropy Simon highlights a piece by Charity Majors that perfectly captures the dynamic between fast-moving AI enthusiasts and cautious AI skeptics within software teams. Majors argues that both sides are entirely correct: missing the AI wave is a genuine existential business threat, but shipping code faster than engineers can read it destroys institutional knowledge and creates a separate existential threat of system incoherence. The core organizational design challenge right now is building natural feedback loops to mend the gap between these two realities.

Simon Willison — 2026-06-28#

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The standout thought today is a philosophical shift on AI-assisted programming via Jon Udell, challenging the phrase “human in the loop”. It’s a crucial perspective for developers—framing autonomous tools as “agents in our loop” rather than black boxes, ensuring we maintain our engineering authority.

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Quoting Jon Udell Simon highlights a thought-provoking quote from Jon Udell about how we frame AI-assisted development. Udell pushes back against the standard “human in the loop” terminology, arguing that it inherently surrenders authority to the machine. Instead, he advocates for an “agent in the loop” approach where developers maintain their standard workflows and simply invite agentic software in to assist. It is a necessary reminder to treat generative AI as a tool that serves the engineering team, rather than an unreviewable black box that just takes prompts and emits features.

Simon Willison — Week of 2026-06-25 to 2026-07-03#

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The single most impactful release this week was Simon’s launch of llm-coding-agent 0.1a0, which successfully turns his popular llm library into a full-fledged coding agent capable of file manipulation and command execution. Bootstrapped entirely using Claude Fable 5 via test-driven development, this represents a massive leap forward for his CLI ecosystem and a brilliant showcase of using frontier models to build the very tools that will orchestrate them.