140 to 40: What I Learned About Owning Watches

This is the second half of the field guide that came out of buying 140 watches over 24 months. The first half covers buying. This one covers living with them.

You wear one watch at a time. This sounds obvious until you own 140 and do the math. That's 139 getting no attention on any given day. Knowing that doesn't stop you from buying. But it does change how you think about what's worth keeping.

It's easier to buy than to sell. I've held watches longer than I wanted to because parting with them is harder than acquiring them. The hunt has a dopamine loop. Selling has friction, second-guessing, and a small tax on your ego. I've gotten better at it. I'm not cured.

If you haven't worn it in 60 days, start asking questions. Not a hard rule, but a useful one. Sixty days is long enough that most watches get a fair shot. It's short enough to catch the ones quietly collecting dust. The question isn't just "did I wear it?" It's "did I have a reason to wear it and still didn't?" Those are different questions.

There's a category that earns an exemption: the watch with a defined job. The formal event watch. The beach watch. If you haven't had the occasion, that's not the watch failing, that's your calendar. The rule applies to watches without a role, or worse, watches whose role got taken.

That last one is the harder call. My Marin Instruments Skin Diver in Taupe was my watch of last summer. Pool days, beach days, it was there for all of them. This summer I've moved to the H. Moser & Cie Pioneer Centre Seconds in that slot. The Marin still sits in the box. It earned its place. It did its job. But I'd reach for the Moser now. That's not a rule problem. That's a decision I haven't made yet. Maybe it goes to my son. Maybe I sell it. The watch deserves better than a box.

When you sell, you think harder than when you keep. Keeping is passive. Selling requires you to make a case, argue both sides, and land somewhere. There's a real cost to selling, so I don't take it lightly. The watches I've let go are the ones I've examined most carefully. That examination is the lesson. A friend of mine at @chronopursuit half-jokes about forming an Investment Committee to buy a watch and an Exit Committee to sell one. We both work in finance and the joke lands because it's also just correct. At work, we think hard before buying and harder before selling. Why would watches be different? The goal is different, though. At the office we're trying to create alpha. On my wrist I'm trying to create happiness. Those require different frameworks.

A strap is the cheapest way to own a new watch. I have a real strap drawer. Bespoke makers, a wide range of leathers, rubber, fabric. I love straps. The A. Lange & Söhne 1 in white gold is a serious watch. Put a blue strap on it and it's one thing. Taupe, another. Black, another. Recently I bought a patterned Paris leather strap from Bulang & Sons on a bit of a gamble. It paid off. That strap costs a fraction of what the watch cost and gave it an entirely new personality. One watch, a drawer of straps, and you've got a small collection inside a single case.

A good watch box is underrated. Quality storage keeps your pieces in good condition and gives you a reason to open it.

Almost no one notices your watch. You think most people clock it. They don't. Wear a $300 watch and a $30,000 watch on consecutive days in the same room and see what happens. Nothing happens. I'll be honest: there was a version of me earlier in this journey who was partly buying for the nod. Fellow collectors, people who'd recognize the reference. I went looking for that and got some of it. But it isn't where I am now. I buy for me. The person who notices is a bonus, not the audience.

Liquidity is not equal. A Rolex sells in a day. Most JDM and microbrand pieces sit for weeks at a discount. Know what it'll cost to get back out before you get in.

Every watch brand has a community, and they'll let you in. Forums, Instagram, Facebook. They're not hard to find and most are more welcoming than you'd expect. Don't be a jerk and they'll take you in. The depth people go to on a single reference is genuinely staggering. For the big names you'll find groups built around one model, not just the brand.

If your friend has a watch you want, borrow it before you buy it. Take it for a week. Return it with a $100 Visa gift card and a six-pack. That gift card and six-pack will save you thousands if it turns out you don't love the watch the way you thought you would. I've done this. It works.

You learn more from the watches you sell than the ones you keep. Keeping requires no argument. Selling forces you to make one. Pay attention to what you tell yourself when you're deciding.