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  1. I was walking Nina home from a friend’s house, thinking about Annie Duke’s Thinking in Bets, when it hit me: every choice we make is a bet.

  2. Disappointed Optimists

    I teach a class called Design for Behavior Change.

  3. The Validation Gap

    Years ago I was at a Web 2.0 conference in New York, sitting next to a young guy with the sweetest baby face.

  4. Often when I help a company roll out OKRs, the same thing happens.

  5. I’ve been thinking about scale the same way I’ve been thinking about speed: as something Silicon Valley treats like a moral good when it’s actually just a strategic choice.

  6. I was reading a post on Anthropic’s blog about AI product management, and the author talked about speed as if it’s a virtue.

  7. There’s a Cold War that runs through almost every product team.

  8. People find out I read twenty-three AI newsletters (and unsubscribed from as many more) and immediately ask the same question: which ones should I read?

  9. Last month a product designer showed me her new prototype.

  10. In Praise of Guessing

    Last night at the Lean Product Meetup someone asked me, “How do you set Key Results when you don’t have a baseline?”

  11. Last week I found myself vibe coding a personal OKR app.

  12. You know what’s ridiculous?

  13. A few years ago, I stumbled across a formula from Kurt Lewin, a psychologist working in the 1930s and 40s: B = f(P, E) Behavior is a function of the Person and the Environment.

  14. Last quarter I watched a Stanford student conduct her first user interview.

  15. It’s January, and millions of people have made the same resolution: “Eat better.”

  16. Last week Anthropic released findings from their new AI Interviewer tool.

  17. Yesterday, Sam Altman declared a “code red” at OpenAI.

  18. Last week, Google released Nano Banana Pro, their latest image generator.

  19. The Dancing Bear Problem

    There’s an old circus act where a bear shuffles around on its hind legs.

  20. I got asked again last week: “What’s the difference between KPIs and OKRs?”

  21. Most product teams plan for success, which makes sense until you realize that planning only for success is how companies end up surprised when things go sideways.

  22. Context Engineering for Non Engineers “Prompt engineering is dead,” the podcast guest said.

  23. I’m teaching CS177 Human-Centered Product Management in the fall.

  24. When I tell people my kid is heading to Sarah Lawrence for a liberal arts degree, I get that look.

  25. When AI researchers started obsessing over “taste” last year, I had to laugh.