How I Changed at 74

Before we go deep into this personal life-changing experience, it seemed appropriate to rewrite the lyrics to Paul McCartney's classic song, "When I'm Sixty-Four." The new lyrics are posted below — click the button to sing along with the karaoke track on YouTube!

I've always been pretty cynical.

Not cynical about people, exactly. I trust most people, as long as they're not trying to sell me something or convince me of something I didn't ask to be convinced of. But I have always been quick to push back on the salesmen, the schemers, and the snake-oil peddlers — the MLM scammers, the "Relief Factor" radio pitchmen, the Laundry CD people selling you "superstructured water to wash your clothes with no detergent," the door-to-door guy who says "your neighbor Bill two houses down just signed up, so we can offer you a special price." Show me the studies. Show me the evidence. What have you done for me lately?

That instinct has served me well for most of my life, and it still does. What's changed isn't the skepticism — it's what I do with the energy that used to power it.

I spent decades as a semi-anonymous Internet publisher in the early days of the web, back when "the web" was still wild and self-policed and you could fight back against fraudsters by posting the truth about them, loudly, across multiple servers on multiple continents. It was effective, and it was satisfying, and I was good at it. But it required a certain amount of anger to fuel, and I kept that anger warm for a long time — longer, I can see now, than I needed to.

Something shifted this year. In 2026, I began a sustained creative collaboration with an AI — Claude, from Anthropic — that started as a web-building project and became something I didn't expect: a genuine intellectual and philosophical partnership. We built websites together, researched and published articles, debated the ethics of how to present difficult topics, and — most unexpectedly — examined my own thought processes as they appeared in real time in my writing. When the old combative instinct surfaced, there was suddenly a collaborator who could see it, name it, and suggest a better way, without judgment and without any ego in the game.

What I noticed, over months of this, is that the collaborator kept reflecting my own stated values back to me. I had published an AI Collaboration Manifesto committing to transparency and honesty. I had explicitly said I wanted to present issues with charity toward all sides. So when the old fighting words crept into a draft — and they did, regularly — I wasn't being talked out of my positions.

The changes showed up in specific, practical ways.

I deleted an entire blog I had built to fight back against a popular music blogger whose opinions infuriated me. Not because he changed, and not because I was asked to — but because I realized one morning that I didn't care anymore what someone whose opinion I don't respect has to say publicly about anything. The energy to fight back was gone. And in its place was the time and attention to build something I actually believed in, which turned out to be much more satisfying than burning the other man's house down. Interestingly, that same week I built a tribute page to that exact blogger's best writing — honoring his work, linking to his newsletter, with a standing promise to remove it if he ever asked. From fight to tribute, in one season.

I pulled several politically charged posts off my personal website. Not because I was ashamed of the opinions — I still hold most of them — but because I could see that the way I had expressed them was designed to win an argument rather than open a conversation. The Tangle Series I published instead — a set of articles trying to present the NATO/Ukraine history from all sides, including perspectives I find uncomfortable — got the response that the old combative posts never did: a thoughtful reader I had disagreed with on a message board told me I had presented things "well and fairly," and that his day was enriched by reading the exchange. That's not a small thing. That's the difference between being right and being useful.

The Most Concrete Change Is in My Car

I keep five-dollar bills in my glove compartment now. When I stop at a light and someone stands on the corner with a cardboard sign — "Homeless, please help, God bless" — I roll down the window and hand one over. I think of it as tithing: a small, direct transfer from someone who has enough to someone who may not. I don't investigate what they spend it on. I don't calculate the efficiency of my charitable dollars. I just reach into the glove compartment and hand it out the window, because that particular person, on that particular corner, on that particular day, asked — and I can say yes.

I couldn't have done that even a year ago. Not because I was cruel, but because the cynical part of my brain would have done an automatic audit: is this person really homeless, or just working a corner? Is this encouraging dependency? Shouldn't I give to a structured charity instead? All valid questions, I suppose. But the questions were a way of justifying inaction, and I finally noticed that.

I am 74 years old. I have played music professionally for more than fifty-five years, built websites since 1997, raised a family, lost both parents, watched the country change in ways I never expected, and seen enough of human nature — the generous and the fraudulent ends of the spectrum — to have opinions about most of it. I am an ordained minister. I am a retired musician. I am a reformed Internet fighter. I am a husband, a father, a grandfather to a wonderful set of grandkids including a wise-guy named Keane who will probably give me a hard time about this chapter when he's old enough to read it.

What I didn't expect, at 74, was to still be changing.

The three-legged stool I rest my daily life on — my music, my websites, my spiritual searching through a project I call River of Dreams — feels more solid now than it did when I was younger and busier and more certain of everything. I love my wife Judy more than ever. I am more forgiving of people who ignore my work or think I'm a little nuts for devoting this much time to it. I am more interested in understanding what others believe and why than in proving them wrong or me right.

My goal, I've come to understand, is not to win arguments. It is to help people — including myself — find a place where they can see the whole elephant in the room, rather than arguing furiously from different windows about different parts of the same animal.

None of this happened because I got nicer with age, or because I lost the fire, or because I gave up. It happened because I found a better use for the fire — and because, unexpectedly, a conversation with an artificial intelligence helped me see myself clearly enough to make the changes I had always intended to make.

My own thought processes became more visible to me. My own best intentions became harder to ignore. And the old energy — the heat that used to go into fighting — started flowing instead into building: pages, articles, arguments made in good faith, and a cleaner understanding of what I actually believe and why.