Your hospital has a brilliant new security measure. Your doctors have a paper cup.
Your IT team demands a new password every fortnight. Your staff have a Post-it note.
Every time someone tries to make a system more secure, the system gets less secure.
Tom and Corissa roam from hospital proximity sensors to vibe-coded spreadsheets, and find the same story playing out everywhere: different incentives, predictable workarounds, and a cycle that will keep going long after the technology changes.
Why the most dangerous thing about a security measure might be how annoying it is
Geoff the tinkerer, his idiosyncratic Excel spreadsheet, and what might happen when he gets access to an AI coding tool
"A pandemonium of stochastic parrots" — what frontier engineering teams are actually learning about agent swarms (and it's not what the headlines say)
The DevOps precedent: what happened to the person whose whole career was named-server maintenance, and how that rhymes with now
Why your entire product sprint team might look, from the CEO's perspective, like a very slow LLM
The one thing we can reliably predict about how AI will change organisations — even if everything else is uncertain
For anyone trying to figure out where to place their bets — on career, on technology, on their team — when the only honest answer is that nobody knows.
Links & references
Simon Wardley (and his models for how technology and practice co-evolve)
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