I had wondered about how trans people would play, and I’m glad to know that my local co-ed softball league has a good policy about this.

Remember when following tech news was a way to avoid confronting the most pressing issues in the world?

Today I released Black Ink 2.4 for iOS, featuring a new inline calendar browser for puzzle downloads. redsweater.com/blog/4293…

I remember, when I was younger, hearing people say “I still feel like I’m 20,” and thinking it was pretty unbelievable. But now I’m 51 and … I still feel like I’m 20. I know a few more things, but I am very tied to the personality, ethics, and ambitions of that 20-year-old.

I dunno, maybe I’m crazy, but if you start a company like Automattic, with your own name in it, the board better have a pretty good reason for kicking you out. I’m excited to hear you’re back in the captain’s seat, Matt, both at Automattic and soon (?) on your boat.

I imagine the feelings I have about AI with respect to knowledge work are akin to the feelings trades people had when power tools arrived. Yes, it will put you out of business IF you don’t adapt.

With the advent of mass-market AI, virtually every person alive has the opportunity to multiply their impact on the world by several times. I’m trying my best, and I hope you are too.

If you dismiss absolutely every other positive feature of AI, its ability to empower people suffering from ADHD and similar conditions probably redeems everything negative about it.

I know there are problems with the metaphor, but fire is a good way to think about AI. It’s a fundamental, culture-transforming technology that empowers people to destroy or create. Without fire, so many horrible things would never have happened, as would so many great things.

Over the years I’ve tried to learn what I can about finance and economics. A word that gets thrown around is “arbitrage”, where you essentially buy something that one market thinks is cheap and sell it in another market that thinks it’s expensive. The AI tech today is offering a lot of arbitrage.

If you haven’t found a way to be optimistic about AI, I don’t think you’re trying.

If Democrats win the midterms, I will give every American $6000 from the same funds that Donald Trump is planning to use for his $5000 payment.

If Republicans win in November, you MIGHT get a weird $5K payoff from Donald Trump. If Democrats win, you MIGHT avoid the US devolving into an increasingly fascist state.

Another weird side-effect of AI: I believe that anybody who is getting really good at managing AI agents is also getting pretty good at managing people. At least if they bring humanity to the table as a baseline.

I continue to be in awe of how fast I can tear through issues when AI helps. If everybody in the world whose productive output benefits society used AI, I’m confident it would repay whatever costs there are.

Congrats to my friend @johnbrayton who just released a major update to Unread, his RSS reader for iOS and Mac! www.goldenhillsoftware.com/2026/09/u…

A reward for those Core Intuition fans who never removed the feed from their podcast app! Episode 27.1, including our reaction to the Apple announcements and some of the AI implications. coreint.org/2026/09/e…

We rewatched “9 to 5” starring Dolly Parton, Lily Tomlin, Jane Fonda, and Dabney Coleman. Really ahead of its time and a great way to remember and celebrate Dolly. Amazingly, the director and co-screenwriter, Colin Higgins, was the writer and co-producer of Harold and Maude!

I threw some veggie taco meat on this pizza. It was good.

IMSO (In My Strident Opinion) you can choose to use AI to be more fake, or to be more real.

A really great, IMO irrefutably great, aspect of AI is that it can unstick your pursuit of progress in almost any field. I’m learning so much about everything because, if I get stuck, I can ask Claude or Codex or Gemini. To use a college metaphor, they are ubiquitous, always on-call TAs.

Imagine how bad the outage at Claude must be if Claude itself can’t fix it in 5 minutes.

Did it lead to a desperate/shitty decision? x.com/dhh/statu… (Tweet text responding to 1Password venture funding: “[…] I fully expect them to go to shit. 1PW now need to beome a many billion dollar company OR DIE TRYING. That usually lead to desperate/shitty decisions.”

Zohran Mamdani is the first mayor I can recall, in my lifetime, who appears to be having the time of his life being mayor.

Like most people, I sometimes quickly turn to my phone and search for the answer to a question. But when the search engines come back with AI results, and I choose to share them, I always say “AI SAYS:” … it’s important to maintain the flimsiness of an attribution.