For Twenty Years, Regret Drove My Watch Hobby

I’m four months into shoulder rehab for a torn rotator cuff, and I’m sad to report that after laying off Motrin for 36 hours, the pain and inflammation came roaring back in my left shoulder. Not surprisingly, during these last four months of shoulder obsession, my watch obsession has taken a back seat. About a month ago, I did a brief experiment with my collection: I put bracelets on three of my Seiko divers. That lasted less than a week. All seven of my divers are back on straps.

I’m not currently buying or selling watches, and I don’t have much left to say about my collection that I haven’t already said. But my all-consuming watch obsession has transferred to healing my shoulder, and that distance from the hobby has given me a few insights I didn’t have before. I realized I’m not just a watch addict. If I peel back the layers beneath the shiny timepieces, what I’m really addicted to is regret. For twenty years, regret drove my watch hobby. The thrill wasn’t owning a new diver; it was convincing myself I’d bought the wrong one. I always needed something better, so I’d sell the old one and replace it with a new model. Then one of two things would happen: I’d miss the old one or want to replace the new one with something even newer. Either way, regret was the engine. I was constantly second-guessing myself and spinning my wheels. My watch hobby became a soap opera with the same tired plot: What Could Have Been.

Regardless of the purchase, I was overwhelmed with regret. I bought watches that were too big, too small, too dressy, too blinged-out—each one a personalized regret grenade.

Letting the collection creep past seven was another fiasco. Anything over that number triggered what I call “Watch-Rotation Anxiety,” a condition where choosing a wristwatch feels like negotiating a hostage release.

When the regret overwhelmed me, I tried to smother it with another purchase. A new watch fed my brain with fresh dopamine and adrenaline, but it was just a band-aid. Regret always returned.

As I descended into this regret-feedback loop, I entered a phase I call Gollumification. Gollum didn’t turn into a demon overnight—his soul disintegrated over centuries. Like a Holy Grail diver watch, the Ring promised specialness, superiority, and shortcuts to power. He committed desperate acts to keep it. He murdered and then lied to himself about why. Clinging to the Ring as his last scrap of identity, he withered into a sad, lonely creature.

That’s why Gollumification resonates today—it’s a slow-motion collapse. You don’t need the Ring to become Gollum. Any addiction will do. Isolate yourself, feed an obsession, and treat your desires as the only truth that matters. Eventually, the human being disappears and Gollum takes over.

So has this distance from watches cured me of my inner Gollum? No, not really.

I’m still addicted to the soap opera of regret.

Regret addiction is very real for me. I’m going through it right now, but not with watches—this time it’s computers. I spent six months researching a desktop to replace my seven-year-old Windows laptop. Recently, I bounced back and forth between a small form factor Windows machine and a Mac Mini. I ended up buying two Mac Minis—one for me and one for my wife. She’s fine with hers because she’s used Mac OS for the last decade, but I’ve been on Windows.

For the last three days, I’ve hated my life. The Mac Mini is a great computer, but I miss Windows. I miss the way Windows accepts all my peripherals—mechanical keyboards, printers—without any fuss. I don’t feel at home on Mac OS at all. I’m actually using Google Chrome on my Mac Mini. Why? Because I’m homesick for Windows. It’s like the American who goes to Paris and misses home so much he goes to McDonald’s just to feel normal again.

That’s where I’m at. I’m overcome with regret.

Here’s how bad it is: Yesterday, after my workout, I wanted to get on a computer for fifteen minutes before taking a nap, and I didn’t want to use the Mac Mini. I resented it. So instead I went into my room and used my old Windows laptop—just to get a taste of home.

My engineering friend Pedro is coming over this weekend to help me connect my peripherals to the Mac Mini and teach me how to use the command keys on my mechanical keyboard so I can feel more comfortable. He assures me the regret is temporary, a necessary transition that will fade as I acclimate to the Mac Mini.

We shall see. The thing is: I think I’m addicted to regret.

All of us are. Go on watch-message boards and you’ll see watch obsessives crying for help—paralyzed by indecision, regret, self-doubt, and lost Holy Grails.

I suspect the watch hobby is just a proxy for the human hunger for high stakes. If you’re full of regret, the drama makes you feel like you’re in a meaningful battle. You’re a man living too comfortably inside the cave with your WiFi, your Internet, your Netflix, and your Cocoa Puffs. You need adventure. You need a deep-sea diver on your wrist while navigating Google just to feel like you’re sailing the Seven Seas.

Regret is the soap opera of suburban man. He’s trapped in his cave and wants to escape, but he also wants to avoid traffic—so he’s stuck. To escape his confinement, he creates soap operas in his mind. And in doing so, he discovers that regret is a powerful tool. It fuels his watch addiction, and when that addiction quiets down, the hunger for regret leaks into other decisions: Windows or Mac, Honda Accord or Toyota Camry, Thai or sushi.

Regret makes inconsequential decisions feel consequential. When we confront this truth, we see how ridiculous we are.

It’s time to turn the page and move on to the next chapter. I just hope the next chapter is one without a sore shoulder.

That’s it. I can’t go on anymore. I’m overcome with regret.