It was late after work, and we were sitting around the table, dice in hand, talking.  The scene had been set by our DM. We were a ragtag band of religious missionaries trying to save a city from being slaughtered by Coalition forces.  After the enemy army had ambushed the army in a nearby field, the Coalition forces besieged the local city nearby, blaming a spy for the ambush. If we weren’t able to locate the spy within a week’s time, the Coalition forces would raze the entire city and slaughter the innocents.

We were faced with a pressing problem.  Unfortunately, our problem wasn’t finding the spy.  We had four hours to play, and we had spent over an hour discussing the best path forward and failed to come to a definitive plan.  Here we were playing along in a world of our creation, and we seemed to be paralyzed by the idea of messing up, doing the wrong thing, and dying.

This experience made me think a lot about what Dungeons and Dragons and other Tabletop RPGs represent.  I think the best way to sum up my thoughts is this: Losing isn’t what you think it is.

For many people, the point of games is to win them.  Winning typically means accomplishing the task set before you.  In chess, this means putting your opponent in checkmate. In D&D, this typically means accomplishing the goal the DM puts in front of you or achieving your character’s desires.

Despite this, it’s important to remember that the potential outcomes of D&D don’t always correlate with whether or not your characters accomplish their stated goals. When you walk away from a session, whether or not you succeeded is a very small aspect of what’s important.  The most important part of any particular game is this: did you have fun?

Take my game as an example.  By the end of the session, we identified the spy and saved the day, but we had spent half of our entire session just discussing strategy.  I was content that we had succeeded. We had done everything so safely. Somehow, we had managed to avoid a single mistake, and this meant there hadn’t been any risk.  Never once did I think my character was in real danger. While my party members enjoyed the session I lot, I enjoyed it but still felt hungry for more action.

When I discussed this with my friends, they said they understood my point, but they mentioned how much it would’ve sucked if something had messed up.  “We could’ve died!” said one friend.

This is where “winning” is so non-traditional in D&D.  You win in D&D if you have fun, and you can have fun if you make great stories.  Whether they are stories of triumph or a fun tale of how your party botched their mission, you have fun when you’re talking about a session for months afterward. 

On the upside of making a risky choice in D&D, you might have more fun putting things on the line, and if your risk succeeds, your character is even closer to the goal, which feels good. 

On the downside, your character is farther from your goal, which might stink, but these sticky situations can make for great stories.

How do your characters pull the party back from the brink?  If they don’t recover, how does a character heroically die? While a character death or TPK might occur, both of these leave you with more stories and more fun. In both the positive and negative outcomes, you’re having fun.  You’re winning the game.

While I know this might be my own opinion, I’d recommend all D&D players to take more risks.  Remember that the worst that can happen is a character death that leads to a new character sheet and new stories.  Make memories with your friends, and don’t shy away from risky things. Remember that D&D is made up for a reason. It’s a time to feel epic, to feel powerful, to be the hero of the story.  While failure might not feel like a goal, any epic quest has its ups and downs. It’s better to have your triumphs and despair than your small wins and losses. Better to have mountains and valleys than hills and troughs.  So please, take risks. Losing isn’t what you think it is.

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  1. Cool post. As a veteran tabletop gamer, this philosophy is nothing new. But it’s an excellent thing to explain to the newcomers and casual players that end up getting more… “serious”. Winning or losing is not what most tabletop RPGs are really about. You’ve captured that well here.

    Liked by 1 person

  2. No, I don’t have any particular technique or speech about it. If I’m asked about the point of the game in the context of “how do you win,” I explain that having fun is the win. I concede that the experience point systems in many RPGs is kind of a way to keep score, but I explain that getting those points before someone else does not constitute winning or losing. Other than that, I just try to explain/show new players that having fun and making a great story are the goals. I think it’s a very difficult idea to convey other than through actual play. “You’ll see” is a good way to start the explanation 😉


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