What’s the best way to work towards owning your ultimate watch? Stick to your principles – and your budget – to accumulate a wide collection? Or level up by trading in and upgrading from one watch to the next, working towards that horological holy grail? Two watch experts argue their corner and put forward different approaches to reaching those goals.

I own more watches than is strictly necessary, if you even accept that a wristwatch of some kind should be part of your life (it should). I don’t regret the life choices they represent, but from time to time I take a long hard look at the collection and confront the reality that a few of them are gathering dust. This isn’t great news for the watches, as they really should be worn to keep them in good order, but more fundamentally it makes me ask why they are there.

Not all of them – some have a guaranteed place for life thanks to their sentimental importance, regardless of how infrequently they grace my wrist. But sometimes it can be healthy to trim the dead wood, particularly if they could be traded in for something I’ve had my eye on.

I don’t think watch collecting should be entirely about levelling up, like some ruthless luxury RPG. But there is something inevitable about the lingering glances we cast on slightly more expensive watches than the ones we own, and the boy math we use to kid ourselves – if I just sell the Tudor and a couple of Seikos, maybe a little dip into my savings, I could get the IWC Schaffhausen Mk XX. A few years later, it’ll be, “Well, the IWC, plus that Omega you’ve had for a while, could see you stepping out in a new Jaeger-LeCoultre Reverso”.

Remember that Canadian blogger who traded a paperclip into a house, over 14 transactions? There’s something about the act of trading in the old for the new that makes you feel like you’re somehow getting an edge, beating the system.

On a more mundane level, we can’t all afford to simply buy every watch that takes our fancy, so an element of “two out, one in” is sometimes called for. Think of it as having your collection in a constant state of evolution – if the right offer comes along, even a watch you’d thought you had locked down for life might be on the table.

Watch collectors love to talk about “grails”, or the “exit watch”: a timepiece that, once acquired, would satisfy their collecting habit for good, leave the itch permanently scratched, allow them to “get out” of the hustle, happy that the one on their wrist is all they’ll ever need. It’s an appealing idea, even if most people who preach it do so knowing it to be a mirage. And yet… how many watches can you wear?

Everyone’s grail is different – they don’t have to be expensive, but they usually are. (This is convenient for the self-deceiving, as they can keep acquiring watches while the white whale remains out of reach.) A Vacheron Constantin Overseas Tourbillon, perhaps, or a perpetual calendar from H. Moser & Cie.? If you can set aside considerations like security and practicality – you might have to keep something affordable for the swimming pool – it’s hard to explain why you’d need anything else.

I’m not saying you can turn a Swatch into an A. Lange & Sohne chronograph by sheer hustle alone. However, reaching your goal in incremental steps can make it a lot more achievable – financially and psychologically – than feeling like you need to put six figures aside in savings before you blow it all at once.

If you’re anything like me, those savings will be burning a hole in your pocket long beforehand, so why not enjoy them in the form of another watch as you continue working towards that grail? That’s what you can tell yourself, anyway.

A decade or so ago, the hot tech marketing buzzword was “gamification” – a suite of strategies and tools that made users stay more engaged with the app (or whatever) and rewarded the users for loyalty and effort. In the years since, badges, rewards and rankings have become part and parcel of our online life.

As someone who grew up on Prince Of Persia and Sonic, I’ve got zero problems with investing some quality digital time mashing buttons and overcoming evil. But I recognise this digital space as a fantasy far removed from my reality (oh, to be as spry as that Persian Prince) and that life is not a game and should not be treated as such.

At its most benign, the sort of habit-forming behaviours that gamification encourages are harmless; at worst, it encourages an unhealthy cycle of dopamine addiction. It’s a type of content you probably don’t need on your phone screen, and you definitely don’t need it in your watch collection.

However, over the years, the discourse of watches has become increasingly gamified. Comment threads are full of watch bros busily levelling up their watch game and generally treating their timepieces like Pokémon. While this language is accessible, it’s not particularly healthy.

The concept of “levelling up” the watches you wear implies that you can “win” at watches. You can’t. At the heart of this pernicious concept is the fact that levelling up requires spending more money, creating a hierarchical attitude to time that does no one any good except – whisper it – the people who make watches.

Levelling up is part of a narrative that validates a particular type of watch journey that isn’t about the validation, but all about the clout earnt for acquiring particular types of watches to get approval from your peers.

Of course, I don’t fundamentally have an issue with people buying lots of watches; that would be ridiculous. I’m all for people buying more watches. What rubs me the wrong way is the mindless speed-run approach of buying a bunch of desirable sports watches and other hype pieces. When people “level up” in this way, there’s often very little care or thought at play. Are they buying these watches because they genuinely like them? I suspect not.

I think it’s far more likely they’re buying them because they want the cool factor and think that having the “right” watches will make them happier, but it doesn’t work like that. They’re not winning the game – they’re fooling themselves.