For me it’s a bit of both - I don’t feel like I need to be checking boxes, but every watch needs to be worn somewhat regularly. I have other hobbies and having thousands just sit in a watchbox isn’t something I want to afford.

I don’t need a chronograph and I don’t need a diver, because I either don’t particularly like the style or don’t think they’re worth the hassle, but I need a dress watch because I actually like wearing them and they make more sense for my lifestyle.

I have an idea of roughly what I’d like to own in the long term, but if I like something and can get a good deal, I’ll get it.

That said, I do also cull my collection pretty aggressively. I tend to only have two watches at any given time, so it often operates as a one-in, one-out rule. In the long run I’ll probably cap my collection at three (dress/daily, dive, and maybe a GMT) or four (I’m likely to inherit a watch that I’ll never sell).

I’m more covering all bases. I got my chunkier diver my Seiko sumo, my classier slimmer watch 36mm DJ, clean and simple, my omega speed master a little more sporty, g shock nuff said, the only other watch i want really is a grand seiko spring.

I don’t have any specific collecting goals beyond buying watches that I enjoy wearing and selling those that I no longer enjoy wearing. So many options at all price points.

For me, it’s been very similar to collecting wine. When I first got into it, everything was amazing and I had to try it all. Costco has a cool looking bottle? Buy! Some winery wants me to join their mailing list? Done!

Watches were the same way. It was like drinking from a fire hose and I couldn’t get enough if it. But after time you become focused. You learn what you like and what you don’t. Same as drinking wine.

Each watch in my collection has a reason to be there, each one tells a story that was relevant to me at the time I bought 'em. I don’t think of my watch collection as a checklist but I don’t think I buy impulsively, either.

How do you relax more? I think the most important remedy is that no-one really cares what watch you wear - or, indeed, if you wear any at all! They have to be meaningful to you alone and that’s it.

90% of the watches I like all look similar to each other. If I had infinite money there are a bunch of watch styles I would never buy, stuff like Rolex datejust for example. I would end up with a huge collection of field and pilot watch variations because that’s what I like.

All that being said, I have occasionally found that I have an outfit where none of my watches fit quite right, and I will try to fill whatever that hole is.

I keep thinking I need a watch with every color dial. But when it comes down to it, I am probably just going to wear a blue one!

You’re hyper-fixating. Find a couple of good, affordable watches that cover a lot of bases and then you can pick up some bigger purchases down the line when you find special pieces and have money set aside. This is a lifelong hobby so no pressure to fill all of those slots right away.

I am very impulsive with most of my watch purchases. Of the 14 watches I currently own only two were north of $800 and only one of those has any real significance (an Accutron Astronaut). I know that I am typically buying a fashion accessory and not a piece of any real horological prestige.

I’m currently researching and shopping for something specific (with a $2000 budget), but that won’t necessarily stop me from spontaneously buying another pretty/cool/interesting $300-500 watch while I am shopping for the right “big” buy.

Personally I just buy what I like, mostly under 500 bucks. The only time I ever really looked for something specific was the last watch I bought, where I really wanted a diver with lumed numbers on the bezel and spent some time searching options.

Do I feel pressured to get my collection “right”? No.

Do I buy impulsively? Yeah, on occasion. There’s been a few under $500 watches that I just bought without thinking. I’ve gotten a lot better about this, though. I fall in lust almost every day, but I let it marinate for a while. If, after weeks or months have passed, I’m still thinking about it, then I’ll probably buy it. Most of the time, I find I forget about whatever it is I was pining after within a few days.

I think it’s impossible to pick the perfect watch. After years of collecting and selling, I’ve learned you’ll refine what you like and go through phases. It’s all part of learning and enjoying the hobby. Stop watching review videos and collection videos and just enjoy the watches you have. Suddenly, the pressure will be gone.

Oh ya its both

I would focus personally on fewer, higher quality pieces vs trying to fill out an arbitrary number in a box.

Over my time collecting I’ve fallen into the trap a few times of wanting to buy a certain kind of piece because I didn’t have something like that covered off in my collection, without pausing to think that maybe the reason why that gap exists is because I don’t like that kind of watch. Inevitably, every watch I’ve ever bought to fill a perceived hole in my collection has ended up getting neglected and then sold.

If I’m debating between two different pieces I’ll sometimes compare against what I already have and buy the one that has less overlap with my current pieces, but that’s about as far as it goes. Ultimately, I would say you should just buy what you like.

And over time I’ve just learned to have a better and better sense of what that really is.

Every watch has to have a role to play within the collection.

That role can be completely and utterly contrived, but a role they must play nonetheless.