Philosopher at Large

16 July 2026 · Edition 32

Systems Owe Evidence. People Do Not.

Log what the pipeline did. Never let the log become a file on the human.

20 June 2026 · Edition 31

Why does AI writing sound generic? It has nothing to work with

Generic isn't a style. It's what comes out when there's nothing to say.

12 June 2026 · Edition 30

The 2 a.m. press check

Twenty-five years under color-true lamps, and the thing Pantone only ever promised.

18 June 2026 · Edition 29

Nobody takes you aside anymore

Print taught a generation when to stop. Then every constraint left inside a decade.

28 May 2026 · Edition 28

How do I get my dev team to adopt AI?

Copilot licenses active across the board. Ticket velocity unchanged after 90 days. The team wasn't lying.

27 May 2026 · Edition 27

Want to learn about agents? Talk to someone who ran an agency.

Yesterday my agents closed 63 issues across six projects. I didn't touch a keyboard.

26 May 2026 · Edition 26

Your AI agents need a water cooler

A friend asked why my AI agents need a water cooler. Turns out it's an immune system.

11 April 2026 · Edition 25

Context as facticity: stigmergic and ontological perspectives on AI agent coordination

AI agent coordination is doing analytic philosophy without knowing it.

Edition 24

26 April 2026 · Edition 23

Content ideas for consultants: how to generate thought leadership from what you already know

Consultants don't lack expertise. They lack a system for surfacing what they already know.

18 April 2026 · Edition 22

The chain was never a chain

After arguing that artifacts dissolve and apps dissolve — what about the roles?

13 April 2026 · Edition 21

Knowledge work was never work

Why do we have PowerPoints? The prior question nobody's asking.

9 April 2026 · Edition 20

The accommodation tax

Every time I ask an AI agent for a change, I still cringe.

6 April 2026 · Edition 18

I ran my AI agency's first real engagement. Here's everything that happened.

Five AI personas. One client onboarding. Fifteen minutes of things going wrong in instructive ways.

29 March 2026 · Edition 17

AI and the Götterdämmerung of Work

AI didn't defeat the myth that human value comes from reliable output — we built the systems that exposed it.

20 March 2026 · Edition 16

Your project management tool was made for a non-human (AI) factory, not for you

Every tool on the market descends from Taylor's factory floor. The assumptions were wrong then.

13 March 2026 · Edition 15

Most of your infrastructure is decoration

Dashboards nobody checks. Reviews that rubber-stamp. Strategy decks that never connect to operations. How much of what you manage is ornamental?

2 February 2026 · Edition 14

When execution becomes cheap, ideas become expensive

The bottleneck moved from building to deciding — and most organizations haven't noticed.

10 March 2026 · Edition 13

Manual fluency is the prerequisite for agent supervision

You cannot responsibly automate what you cannot do manually

3 March 2026 · Edition 12

Your process was built for a different speed

When work changes velocity, governance becomes theater.

28 February 2026 · Edition 11

The work that remains

Speed without understanding is just technical debt with better commit messages.

24 February 2026 · Edition 10

The bottleneck moved

Execution got cheap. Nobody's ready for what that means.

22 February 2026 · Edition 9

Universities missed the window to own AI literacy

The window was wide open. They spent it forming committees.

10 February 2026 · Edition 8

You were trained to suppress yourself

Organizations engineered the machine-self. You cooperated because it worked—until now.

3 February 2026 · Edition 7

We always panic about new tools (and we’re always wrong)

Printing press, typewriters, photography, calculators, recorded music—every time a new tool emerges, we predict disaster. We're always wrong about what's worth protecting.

Edition 6

27 January 2026 · Edition 5