Amazon founder Jeff Bezos on his decision to start an online bookstore in the 1990s:

The framework I found which made the decision incredibly easy was what I called the regret minimization framework. I wanted to project myself forward to age 80 and look back on my life and I want to have minimized the number of regrets I have. And I knew that when I was 80 I was not going to regret having tried this. I was not going to regret trying to participate in this thing called the internet that I thought was going to be a really big deal. But I knew the one thing I might regret is not ever having tried. And I knew that that would haunt me every day. So when I thought about it that way it was an incredibly easy decision.

With unavoidable uncertainty and wild problems, sometimes regret minimization is the best paradigm we have.

// 01.28.26

Basecamp’s Jason Fried’s brief discussion of product development should be required reading for anyone who designs software, including EHRs, PACS, dictation, or whatever new dumb AI implementation someone is pitching to revolutionize healthcare (but that no one talked to an actual doctor about).

The critical tension is the balance between making features obvious, easy, and possible. You have to have opinions, and you have to choose, because being everything to everyone isn’t an option.

// 01.27.26

From Developmental Editing by Scott Norton:

Few pleasures are as great as the taste of a fresh idea. A new insight melts in the brain like chocolate on the tongue. Whether the insight is unprecedented in human history or news only to yourself doesn’t matter; the first time a thought occurs is always magic.

That magic is so fickle, perishable. I always find the strong desire to capture as much of it as possible, and the more I can horde upfront the better chance I have of making it to the finish line of anything.

// 01.14.26

Kevin Kelly, adding 101 new bits to his growing collection of pithy advice. A few of my favorites:

  • Forget trying to decide what your life’s destiny is. That’s too grand. Instead, just figure out what you should do in the next 2 years.
  • Try to define yourself by what you love and embrace, rather than what you hate and refuse.
  • Read a lot of history so you can understand how weird the past was; that way you will be comfortable with how weird the future will be.
  • There should be at least one thing in your life you enjoy despite being no good at it. This is your play time, which will keep you young. Never apologize for it.
  • The patience you need for big things, is developed by your patience with the little things.
  • There is a profound difference between thinking less of yourself (not useful), and thinking of yourself less (better).
    Avoid making any kind of important decision when you are either hungry, angry, lonely, or tired (HALT)
// 01.07.26

From a highly enjoyable “So you wanna de-bog yourself” (about getting “unstuck”) by Adam Mastroianni:

“Declining the dragon” – a medieval knight metaphor for getting unstuck: Sometimes I’ll know exactly what I need to do in order to leave the bog, but I’m too afraid to do it. I’m afraid to tell the truth, or make someone mad, or take a risk. And so I dither, hoping that the future will not require me to be brave.

Everybody thinks this is a bad strategy because it merely prolongs my suffering, but that’s not why it’s a dumb thing to do. Yes, every moment I dither is a moment I suffer. But when I finally do the brave thing, that’s not the climax of my suffering—that moment is the opposite of suffering. Being brave feels good. I mean, have you ever stood up to a bully, or conquered stage fright, or finally stopped being embarrassed about what you love? It’s the most wonderful feeling in the world. Whenever you chicken out, you don’t just feel the pain of cowardice; you miss out on the pleasure of courage.

Medieval knights used to wander around hoping for honorable adventures to pop up so that they could demonstrate their bravery. They were desperate for big, scary dragons to appear. When I put off doing the brave thing, I am declining the dragon: missing an opportunity to do something that might be scary in the moment but would ultimately make me feel great.

The whole post makes for great early January reading.

// 01.06.26

From The World I See, a memoir by the godmother of AI, Dr. Fei-Fei Li:

This, collectively, is the next North Star: reimagining AI from the ground up as a human-centered practice. I don’t see it as a change in the journey’s direction so much as a broadening of its scope. AI must become as committed to humanity as it’s always been to science. It should remain collaborative and deferential in the best academic tradition, but unafraid to confront the real world. Starlight, after all, is manifold. Its white glow, once unraveled, reveals every color that can be seen.

// 12.30.25