Medium

Tim O'Brien

he/him

Featured Book

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Essential: No Algorithm Can Provide a Purpose

Essential: No Algorithm Can Provide a Purpose

Essential is a near-future political novel about AI governance, Canadian democracy, automation, work, and the stubborn human need to matter.

2026

Stories

Tim O'Brien

·

Oct 31

Canada Just Bought Its Own AI Company. I Wrote This Six Months Ago.

Ottawa put $1.6 billion into Cohere in the name of sovereignty. The near future I’ve been writing about is arriving on schedule.

Canada Just Bought Its Own AI Company. I Wrote This Six Months Ago.

Tim O'Brien

·

Oct 13

Who Governs What an Agent Learns?

We need mechanisms that bound an agent’s agency to an approved world model.

Who Governs What an Agent Learns?

Tim O'Brien

·

Oct 8

Wrong Answer. Give Me a Different One.

Challenger, AI agents, and the danger of asking until we get a yes.

Wrong Answer. Give Me a Different One.

Tim O'Brien

·

Oct 6

Dante Put Flatterers in a Ditch of Excrement

Why a difficult medieval poem about Hell is also a very personal diss track — and worth another read.

Dante Put Flatterers in a Ditch of Excrement

Tim O'Brien

·

Oct 5

The World That Agrees With You Now Available

How the personalized internet prepared us for agreeable AI — and why agent memory changes the stakes.

The World That Agrees With You Now Available

Tim O'Brien

·

Sep 21

I Went Hiking. Listened to The Daily. Wrote an AI Cult Novel.

How OpenAI’s Hugging Face incident, a drive through the Cascades, and Michael Barbaro’s ponderous “Huh” became Into Alignment.

I Went Hiking. Listened to The Daily. Wrote an AI Cult Novel.

Tim O'Brien

·

Sep 1

I Proposed a New Job Title. You Had Opinions. So I’m Writing a Free Book.

Five chapters of The Orchestrator are already online — including an exhaustive guide to the tools defining this emerging field.

A hand drawn sketching hand on a book with 3D models of technology.

Tim O'Brien

·

Aug 26

By the Time We Noticed, the News Was Boiling

The ad-funded web degraded journalism over decades. Generative AI needed only a few years to flood what remained.

By the Time We Noticed, the News Was Boiling

Tim O'Brien

·

Aug 23

If AI Generates a Post and Nobody Reads It, Does It Matter?

As content becomes effortless to generate, we’re left asking what — if anything — the human added.

If AI Generates a Post and Nobody Reads It, Does It Matter?

Tim O'Brien

·

Aug 17

Don’t Get Too Comfortable with that AI Skills Map

It’s a good picture of 2026. That doesn’t mean the jobs on it will last.

Don’t Get Too Comfortable with that AI Skills Map

Tim O'Brien

Tim O'Brienhe/him

Book Author

Friend of Medium

I write and I code. Not always in that order. I work on infrastructure and architecture, with a focus on Cloud Cost and Reliability. I also sing and ski.

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