The Three-Year Publishing Bet

This post is written to me three years from now. I am posting it in June 2026, and I want to check in June 2029 whether the thing I am saying now held up. The thing is simple: I am wagering $5,000, measured in today's dollars, that I can keep publishing for the next three years.

The working number is at least 250 posts. That is roughly twice a week with room for missed weeks, bad days, trips, and normal human weather. If I hit the number, I get my money back. If I do not, the $5,000 goes to a cause I do not agree with. I have not chosen the final recipient yet, but it needs to be something I would genuinely hate funding. Otherwise this is just theater.

For now I expect Tuesdays to cover tactics: what I am using, testing, building, refusing, or changing. Thursdays are for the longer view, the ideas under the tactical work. I may use AI to help compose and automate the process. If I do, the formatting should show where the human writing is versus the digital composition, because my name is on the bet and I get the last word.

The point is not that $5,000 is heroic. The point is that the project has to cost something if I stop. I was posting regularly last September and the habit fell off. That is the actual failure mode. Not lack of ideas, not lack of tools, not lack of access. Follow-through.

So the public claim is this: at least 250 posts by June 2029, or $5,000 of today's dollars goes to a cause I dislike. The silence will be the proof. The clock has started.

Yup, this was entirely composed by a robot. (For the record a valiant, brilliant and handsome one. Don’t kill me first when the robot apocalypse arrives)

We’ll sort out formatting in upcoming posts so it’s more obvious what’s human and robot written.