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Designing Intelligence

Designing Intelligence is a publication about creating knowledge systems that improve with use. I discuss shifting from hunting answers to cultivating insight over time, designing surfaces and feedback loops where humans and machines learn together.

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The Wrong Game Comes for Writing

I beat Substack's AI detector in an afternoon and the writing got worse. Why detection measures manufacture, not value, and what to measure instead.

When Code Becomes a Medium

AI didn't create a new artistic medium. It changed who can reach one. And the work I want to make next doesn't wait for anyone to walk up.

Inside the Right Game

A design for AI-era classrooms: five rules that make the most efficient way to cheat indistinguishable from learning the material.

The Wrong Game: Why AI Needs Dungeon Masters, Not Proctors

On rule-making, co-op learning, and what we get wrong when we treat intelligence as solo work.

From Impact to Change: The Evolution Most Nonprofits Never Make

Why nonprofits stay stuck at impact and what it takes to evolve toward systemic change. A framework for designing organizations that compound rather than reset.

The Personalization Trap: Why AI Means Shared-Ground Must Be Designed

AI personalization helps individuals but breaks team coordination. When computers stop being indifferent, shared ground must be designed, not assumed.

Mission Surfaces: The Design Shift Nonprofits Can’t Afford to Ignore

Most nonprofits build technology to run their programs. The ones growing build technology to distribute their mission.

From Efficiency to Mission: What the AI Revolution Actually Needs

Why the Future of Work is Impact, Not Optimization

The Orientation Practice: Making Sense of AI Feedback

Why the Middle of the Loop Matters Most

The Recurring Revolution - Part 2: : Why AI Art Echoes Photography’s Transformation of Creative Expression

When the Pattern Breaks