The most direct answer is resolving the main quest. In many campaigns, the player characters really only exist to pursue the main quest, and resolving that quest is more or less the endpoint of most campaigns. So an argument could be made that "winning" is completing the main quest.
But there's always another quest. Classically, early D&D players carried characters over multiple campaigns, and if that's possible, it feels paltry to say completing one quest is victory. Besides, as I've noted elsewhere, completing the campaign is your character at the height of their power--leaving them there is unfulfilling at best. So while this philosophy has advantages like the concreteness of having a finished quest, there's always going to be another adventure, and that can leave some players wanting.
There's achieving some arbitrary level of power or notoriety with your character. I recall that my second character was a gnomish wizard who schemed and stole and did all manner of things a high schooler would do in an evil campaign, and I really just wanted him to be so powerful no one could touch him. And my DM figured that out from how I played (bless him) and let me just build this character up.
There's diminishing returns there too. Eventually, my gnomish wizard was tricking Inevitables out of death sentences and building massive keeps and decimating militias. And it was fun for a while. But then there was no challenge. My wizard had the whole world in the palm of his hand, but that meant he wanted for nothing. He wasn't fun anymore. The campaign died off, as I imagine many do when the challenge disappears.
You could use character development as a benchmark. If you're roleplaying especially, bringing your character to a certain point narratively--forgiving themselves for some past mistake, making up for a past misdeed, growing in some emotional way--can be a rewarding way to mark what "winning" looks like.
This approach is great, but it cuts you off from the party. Once your character arc is complete, you're pretty detached from the rest of the story in some cases, and since your focus is on your character, you can miss out on main plot and other character moments. If you can keep it all in mind at the same time, it can work, but it's a delicate line to tread, and not everyone pulls it off well.
You could say that "winning" is when everyone at the table gets what they want. That way, everyone is satisfied, right? The combat-focused player saved the day with their new weapon, the roleplayer got to dramatically transform their character, and the antics player nailed a joke that will be a part of the group's vocabulary for life. Everyone's happy.
But is the GM happy? Did the story get served? Did each character get a just ending? It turns out it's more complicated than just everybody getting an individual win condition fulfilled. In fact, individual win conditions mean that people can get left out, and that can be an awful experience.
So how do you actually "win" a tabletop game? Is it even possible?
In a sense, yes. But also no.
Let's tackle no first. You can't win a tabletop game in any way that matters. The game world is bigger than you, and you will never have complete control over it. You will always have new challenges. There will never be a lasting era of victory without something mucking things up. This is just the way things are. So winning is only fleeting if you make it about truly controlling a situation. You cannot win a tabletop game anymore more than you can move the entire world's sand one grain at a time--any effort at it will never amount to anything.
But also in a sense, yes. Any of the philsophies above will grant you a feeling of victory. But as I've argued, there are drawbacks to these. They are incomplete, counterproductive, or inefficient paths to satisfaction. A simpler philosophy works better, though:
Did you have fun?
The entire point of tabletop games is to have fun. Full stop. That's the point. It's why we play. It's why GMs create homebrew material--because it's fun. It's why players meticulously design their characters--because it's fun. It's why players craft combat characters and wade into battle--because it's fun.
So, did you have fun? If you did, you won. You played a game where anything can happen, and the thing that happened (out of all possible outcomes) was fun for you to experience. That sounds like winning. The object of the game was to have fun, and you did, so you win.
This is so simple that I resisted it when I first realized it. I didn't want to believe that I could determine the success of a game experience, from campaign down to session, based on whether I had fun. But I started listening to that philosophy as I kept playing. I realized I'd been writing campaigns for others without my interests. I'd been running a campaign I didn't enjoy. I wasn't having fun with any of it. I changed things in my writing, dropped the bad campaign, and resolved to make fun my metric.
Since then, I've run my favorite campaign I've ever done, Of Gods and Dragons, which has been nothing but fun. Setting fun at the center of your campaign is the easiest way to give your players a good time, and if you're a player, choosing fun as your win condition is the best thing you can do for yourself and for those in your group.
So, insofar as its possible to "win" a tabletop game, the method is simply to commit to having fun. If it's not fun, you're in a bad group and need to find a better one. If it is fun, you've gotten out of the game what you hoped for. It can be that simple if you let it.
That's all for now. Coming soon: a pirate D&D one-shot, a guide to the planes, and what perfect GMing looks like. Until next time, happy gaming!
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