MoT's WDF

So for a while now I have been thinking about parting ways with some of my watches in order to help fund a bigger purchase, like a BB GMT, some sort of Speedmaster, or maybe even a Railmaster or OP39.

The thing is, none of my watches are worth much more than a couple hundred dollars, with maybe 3 close to $500. A few Hamiltons, a couple Glycines, and a few other odds and ends like Victorinox and Steinhart. Where do you draw the line between the usefulness of the watch vs. the return you'll get for it towards something else?

I wrestle with this sometimes myself. My advice is to start by selling the ones that don’t get any wrist time (assuming no sentimental value). Those are just taking up space when someone else could be enjoying them and you could put some money toward whatever you’re saving up for.

Next, I’d think about which ones I wouldn’t miss if I sold them. If you sold it, would you be tempted to buy it again the next time it showed up in the Deal thread? If so, maybe you should hang onto it. If not, consider creating an eBay listing and letting it sit there at a price you’re comfortable with. No need to sell quickly or compromise on your price. You can reconsider this approach if several weeks/months go by without any activity. I just sold a Vostok this way last week and got more than I paid for it because I had the luxury of time and patience.

I hope this is in some way helpful. The other thing I’ve found is that I get enjoyment out of having watches come and go because it helps me better understand what I really like... and it helps me keep my collection to a reasonable size.

Good luck whatever you decide.

I decided a couple years ago to downsize from a large collection of affordable to a small collection of mid-priced watches. Since then, I've continued to flip watches, but have stayed at 3-4 pieces. Some of those have included the Speedmaster and Railmaster you mentioned. It's been much more fulfilling for me, personally. Once you get down to the size collection you want, as long as you can accept a one-in/one-out rules as the way it has to be, it's not so bad.

I did try to reduce my collection to one watch at one point, and for me that was too prohibitive. It was interesting to try though. One useful way for met to reduce my collection was to identify when multiple watches would each be appropriate for a given activity/clothing/trip, and try to reduce to one that would fill that roll.

IMO, it's not simply about how much cash you can recover, it's about reducing clutter. The only thing that holds me back from getting rid of more stuff is I find the whole selling process odious.

More things means more to maintain, to worry about losing, breaking, or having stolen, to have to deal with any time you move or reorganize. Possessions are a prison.

I find with selling watches the best things to do is go slow, and follow your gut.
It may feel good to emotionally sell off a bunch of watches chasing contentment or the release of some sort of possession-claustrophobia, but too often you'll wind up with regrets.
I personally treat the buying and selling process similarly (or try to ). Wait a couple weeks to a month and see how you feel about it then.

I did this with several of my hobbies and never regretted it. Learning to declutter is great for the mental state as well because once something you don't excessively value is gone, it clears up some mental space.

I'm also the type of person who will wear 1 watch a week or 2 before swapping so my opinions may not be as useful.