Everyone wants to win. It’s how people are wired, and it’s the goal of the game. Whether it’s a battle or difficult negotiation in a roleplaying game, a 1 vs. 1 fight in the myriad fighting games available, or a team deathmatch in your favorite shooter, everyone seeks victory. After all, it’s fun to win.

But not if I win all the time. Paradoxically, while I love to win, winning all the time makes it not worth it anymore. Winning becomes too easy, and so I grow bored of playing at that point. With no challenge, there’s no sense of accomplishment.

So naturally, we should just ramp up the difficulty so it’s nearly impossible to win, right? Not so fast, chief. It’s not fun to lose all the time either. Of course, if the challenge is meaningful, and incremental progress toward victory is possible, then lots of challenge is good. This applies more to single player games than multiplayer games of course. In multiplayer games, challenge is found by finding appropriate opponents to play the game with, or a GM who runs a game of appropriate challenge in the case of tabletop rpgs.

In any case, the trick is to find the sweet spot where victory is out of reach, but possible to attain through some effort. In competitive games, this is finding someone you can win against at the ideal rate for you. For me, this is someone who almost always beats me in the game. If they can beat me most of the time, it makes victory that much sweeter when I attain it, and it teaches me a lot more about the game. Like life, in gaming we also learn more from our failures than our successes.

In a roleplaying game, the trick is finding a GM who knows how to balance encounters to remain tense, and isn’t afraid to kill off the PCs. Or at least defeat them, then use one of these handy tricks to continue the game, or another one he may have up his sleeve. By challenging the players, he gives them something to strive for, and success is never certain.

Now, the crux of all this is that a game will generally be most fun when it provides a difficult, meaningful challenge to those playing it. This means that victory won’t come easy, but with the enough effort, it will come. When victory is attained under these conditions, there’s a real sense of accomplishment, rather than the hollow feeling that comes with assured victory. And even if you lose, the thrill of the challenge should still provide you with a good time, as should the suspense of what happens next and the sense that victory could be right around the corner.

I’m not saying it isn’t dissapointing to lose, it usually is after all. However, if it’s a good game, losing can still be fun. It also provides a chance to learn more about the game you’re playing, and apply those lessons next time you play. Not only is this good for the entertainment value that comes with playing the game, it also prepares you for the successes and failures that come with life. Learning to deal with the emotions that come with winning and losing while playing a game lets you get used to the idea of success and failure when the stakes really aren’t that high. Unless you happened to be involved in a tournament anyway, but that’s beside the point for now. Once you learn to deal with the emotions of winning and losing in a game environment, you can apply them to the more serious successes and failures that come from living. It’s definitely a valuable skill to have.

In any case, if you always go for the easy games, try out some challenging games. When I say this, I mean relative to your skill level, not what other people say is easy or hard. Don’t get frustrated when you lose, just get back to it and try to do better next time. I think if you keep at it, you’ll find it far more rewarding to succeed at a challenging game than one that isn’t challenging. In addition, you’ll learn patience, as well as how to deal with success and failure, and how to learn from your mistakes. Finally, you get to do all this while playing a game and having fun. Sounds like a sweet deal to me.