Critical Failures: What Dungeons & Dragons Taught Me about Storytelling
Imagine you’re writing a story about a fistfight. Your protagonist is great at punching, and he’s facing off against a total jerk with a totally punchable face. In fact, this is supposed to be the scene where the reader learns that your protagonist is a really cool guy with really powerful fists.
But now imagine this: every time your protagonist tries to throw a punch, you have to roll a die to see if he succeeds, and you roll terribly. Instead of impressing everyone with his right hook, your cool protagonist flails around and gets beaten up by a jerk. It doesn’t matter how much you or your readers wanted him to succeed; he just didn’t.
So what story are you going to tell now? How do you go on writing about this now-somewhat-less-cool protagonist, knowing that the dice might never come up in his favor?
Welcome to telling stories — or trying to — in Dungeons & Dragons.
Writers love to talk about how stories get away from us. Our characters have minds of their own, our plots take unexpected turns, and sometimes we don’t even know what the story is about until we’ve written it. But when it comes down to it, we control what goes on the page.
In D&D, it doesn’t work like that. Like most tabletop RPGs, D&D is built on the uncertainty of the dice. As such, D&D is chock-full of frustrating, unexpected, sometimes spectacular failures; no matter how expertly you stack the odds in your favor, disaster and death are always just a roll of the dice away.
It can be tempting to see a story as “ruined” when it doesn’t go the way you expect it to, or when your cool protagonist falls apart under pressure. Every D&D player has a story or two about a critical failure that ruined their day, upended their campaign, or killed a beloved character. This is balanced, of course, by the fact that every roll comes with a chance of dazzling success. But I would argue the real balance comes from the narrative potential of our failures.
Failure can signal the end of a character, but it almost never signals the end of a story. It often represents the narrative options we consider bad — confusing, painful, jarring, and unsatisfying. Because we don’t want those things to happen, we don’t usually see the value in them. It’s rare that you’re looking for a low roll of the dice — you want to pull off your crazy plan, you want to bat your eyes and charm that dragon so it thinks twice about incinerating you and your friends. But every branch of a story opens up new possibilities, and sometimes the most interesting, unexpected, and compelling stories can be found among the branches that follow an unmitigated disaster.
My favorite D&D game of all time reached what should have been its grand finale a few years ago: a battle for the fate of the world against a terrifying cult in which our party of daring adventurers came together and triumphed over evil, etc.
Except we screwed up. Not only did we fail to stop the bad guys, but two members of our adventuring party died, a third betrayed us, and to top it all off, we failed to warn two major cities of the bad guys’s plans, resulting in those cities being wiped off the map.
What should have been the end of that story became the beginning of a far more powerful and interesting one — one which would be permanently marked by the humbling realization that we could lose and a newfound desperation to win, to make up for our mistakes, to protect the people we had left. It showed that the story truly hinged on our choices, both the good and the very, very bad.
This is often a place where branching stories in other mediums fall short. True failure results in a dead end or, if it’s a Choose Your Own Adventure book, in being eaten by a tyrannosaurus Rex, which is also a dead end. (It’s been roughly 20 years since that first happened to me, and I’m still salty.) This kind of failure is a closed door, a Game Over screen, not an invitation to new possibilities.
Some failures in D&D can feel like that, but even when something happens that I genuinely regret, I find that it teaches me more about the story I would have liked to tell; living through the failure and seeing the other side of it makes the other possible outcomes shine brighter in my mind, and that becomes fuel for the stories I write in my own time. It’s like how comedy and tragedy often go hand in hand: the grimmest stories need a touch of goodness to keep perspective, and joyful outcomes can be felt more deeply when they come after the possibility of heartbreak and disaster has been explored. By its very nature, D&D is an exercise in what ifs, and being cognizant of a full spectrum of possibilities is a great skill for a writer to exercise.
Because this is how failure works in real life: you trip going down the same flight of stairs you’ve walked down every day; you screw up a recipe you’ve never screwed up before; you don’t get that promotion, and you’ll never know why. Failure can spoil our image of ourselves, just as it spoils our protagonist’s image as a cool guy with powerful fists. Our bodies and minds break down unexpectedly, and success slips from our grasp, sometimes for no reason at all. Some stories try to teach us that, while others function as an escape from the painful randomness of life. But far more rarely do we get to experience stories that hold us right in the middle, on the knife’s edge of chance, breathlessly watching the dice fall.
