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Context & Chaos

A human-first community newsletter exploring the future of context engineering and AI. One story, one lesson, and one shared insight at a time. Curated with 💙 for the humans of data & AI.

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Gartner Hype Cycles 2026: Nobody Owns Context

314 obstacles across ten reports, and a vacancy sitting between two org charts

Your Agents Are Code. Stop Governing Them Like Documents.

You cannot inventory agents fast enough to govern them. You can govern the parts they are made of.

AI Slop Produced by a Human Is a Yellow Flag

Adoption numbers tell you people are using AI. They don't tell you if the company is getting more capable.

I Got Long

Why context portability is the threat most AI programs cannot see yet

The GitHub for Context Doesn’t Exist Yet

A walkthrough of my talk at the AI Engineer World’s Fair: two eras of building agents inside my own company, five stack migrations, and the infrastructure question I left the room with.

Your AI Dashboard Is Hiding Its Worst Failures

The metrics that look green on the dashboard are the ones hiding where your system actually fails. Aggregate metrics show the average and conceal what matters most.

Production AI & The False Finish Line

Why the accountability gap in your AI deployments was decided at the go-live celebration

How to make Satya Nadella’s vision a reality

What it takes to build the learning loop Satya described, and why most organizations leak it before it compounds.

The Godfather Problem

Your AI’s context has a floor. Most teams have never measured theirs. Here’s the one number I use.

Snowflake Summit 2026: Everyone Owns Context Now

Nobody owns the Hard Half. Technical context had a stage. Organizational context didn't have a booth.