😬 I let AI analyze 2 years of my conversations. It got uncomfortable.

After two years using AI to improve my work, I recently turned its superpowers on myself.

With hundreds of our chats offering a window into my soul, I asked ChatGPT some uncomfortable questions:

• What do you know about me that I don’t know about myself?

• Where am I playing small?

• What lies do I tell myself to avoid uncomfortable truths?

We recorded it all in real time — my most soul-baring YouTube video yet.

(Here’s a free PDF of the 11 prompts I used.)

To watch ChatGPT play coach, therapist, and butt-kicker, click the image below ⬇️

Last week, the Washington Post fired 300 journalists, including Ron Charles, the Post’s longtime book critic and one of my favorite writers. The good news: Ron now has a Substack newsletter. Bookworms of the world, subscribe!

In honor of Milano Cortina 2026, we’re rolling out a new 60-second format: Olympic Podium. Bronze, silver, and gold medals for everything from pizza toppings to things that should be illegal. First up: Competitions that should be in the Olympics.

Kevin Kelly is among the wisest, most creative people I know — one of the minds behind Wired Magazine, The Whole Earth Review, the WELL, Recommendo, Cool Tools, and more. So, when he told me he wanted to combat cynicism with a podcast called “Best Case Scenarios,” I said, “Go for it!” And when he asked whether I’d like to play along — essentially to be Gilligan to his Skipper — I said, “Hell, yes.” You can find the first few episodes — about optimistic scenarios for energy, transportation, and brain science here.

Still digesting your Super Bowl chicken wings? It might be time for a “fart walk.” Both Food & Wine magazine and Harvard gastroenterologist Trisha Pasricha swear by it.

I’ve been introspecting. Now it’s your turn.

The results of last edition’s poll show that you and I are kindred spirits. We spend way too much time processing email and over-polishing work. (Wait, does “over-polishing” need a hyphen?)