Category: AI

  • Keywords: Hedgehogs and Foxes (and AI, oh my!)

    What kind of thinker are you? Knowing the difference between when you’re a hedgehog & when you’re a fox can be empowering. The following piece is part of a “Keywords” series that I’ve slowly built over the history of The Dispatch. Before we start, though, I want to share that Claude was helpful developing my argument in a…

  • Is AI Slop Good for Brick and Mortar?

    Will untrustworthy AI products and advertising breathe new life into retail because that’s where trustable humans are?  It was spring. I walked the streets of New Delhi reckoning with an urgent Number Two and no place to deposit it. Public toilets, at least in that hood, seemed not a high municipal priority. Then, through gastrointestinal-distress-blurred…

  • Retro Futures: “Sneakers” (1992) and Anthropic’s Mythos (2026)

    How does an early 1990s caper movie help us understand the threat and promise of today’s sharpest-edged AI models?  On April 7th, Anthropic announced that it had created Mythos, an AI so powerful that it can find long-undiscovered software bugs, making banks, hospitals, and other key holders of personal data vulnerable to hackers and scammers.…

  • The Cosplay Reality Collapse

    With humans pretending to be AIs, fiction pretending to be history, and chatbots encouraging humans to commit despicable acts, it has never been harder to know what is real. A couple columns back, I asked “Do We Already Think AIs Are Conscious?” The provocation was an interesting “hit piece” that an AI agent had written…

  • No Experience is Wasted…

    …if you can think analogically: a mini-memoir. Last week, a young colleague and I visited La Profesora’s Digital Skills class at Portland State University. We were there to talk about career readiness and what my friend Rishad Tobaccowala, in his terrific book Restoring the Soul of Business, calls “the turd on the table.”** In this case, the…

  • Do We Already Think AIs Are Conscious?

    When an AI Agent wrote a hit piece about a human, the press paid attention. But they didn’t look at the user comments. Here’s what they missed. When it comes to AI, my writerly beat is how human behavior changes in the face of AI. While I am interested in existential questions around AI, I’m…

  • Interpersonalization

    Does the marketing dream of AI-generated ads for every person make sense? Digital advertising uses all the data it has about you (which is a lot) to draw conclusions about the things you want and then place ads about those things in front of you. My friend (and media deep thinker) Jim Meskauskas describes the worst-case scenario…

  • Thought Flavors

    Different tools can unleash different kinds of thinking, including fountain pens (a recent interest). Lately, I’ve gotten into fountain pens. A couple years back, my friend Rob gave me a nice Pilot. Then, after they went to Paris on a long-delayed mother/daughter trip, Kathi and Helena brought back a Waterman for me. I had an…

  • Will Teach for Food: a Mini Memoir

    Today’s job market for recent college grads eerily resembles the academic job market in the 1990s: what are the lessons? The great graduate job drought, a dejecting article by Anjli Raval from the Financial Times ($) arrested my attention this week. Recent college graduates face long and difficult job searches. In the U.K., there are 140 applicants…

  • Leaps of Faith (but not that kind)

    How can we escape closed-loop thinking? (Hint: it’s not logic.) La Profesora turned me onto a recent episode of Your Undivided Attention, a podcast by Tristan Harris and Aza Raskin of The Center for Humane Technology. In “What Would It Take to Actually Trust Each Other? The Game Theory Dilemma,” Harris and Raskin talk with Professor…