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)
• Clayton Christensen (Innovator's Dilemma, disruption theory)
• Episode 134: Geoff's shadow spreadsheet sprawl https://shows.acast.com/tentacles/episodes/696fea603738e9e7d196e2f5
• Episode 127: The unbundling and bundling of jobs https://shows.acast.com/tentacles/episodes/6920570d4105c9a02176f2bc

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