Archive - Becoming Cyber

The Pipeline Paradox: The Experts AI Needs Are Getting Harder to Make

Every verdict an AI agent reaches still needs an experienced practitioner behind it, while the real cases that trained those practitioners are thinning…

Oct 15

The Machine Is Taking the First Look

Security has automated parts of its entry-level work twice already. A third wave is underway, and on the cases it reaches, it now looks before any new…

Oct 1

September 2026

We Are Automating the Job That Made Us

Almost everyone senior in security came up through the entry-level seat. I spent 2021 telling career changers it was safe to come.

Sep 17

The Door Narrows When Every Cybersecurity Hire Has to Be Safe

Cybersecurity has been unusually open to people arriving from other fields. That openness had a source, and the source is changing.

Sep 3

August 2026

Nobody Called It an Apprenticeship

The Apprenticeship Problem: Rebuilding Expertise in the Age of Agentic AI.

Aug 20

Becoming Cyber returns on 20 August

A short note on where this newsletter has been, and what it is now about.

Aug 15

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