Dungeon-Mastering and the Art of Failure

Or, How to Fail Forward IRL and Have Fun While Doing So.

Today, we're going to talk about imposter syndrome. Partly because mental health more broadly is a topic that I think is important to address, but mostly because this is something I struggle with all the time.

According to Psychology Today, imposter syndrome is the feeling that you aren't as competent at others think - and that some day, people will discover the truth about you.

I feel like graduate school is tailor-made for creating imposter syndrome: a PhD is an exercise in realizing how little you know about the topic where you are an "expert". Between the journal papers, and job searches, and grant applications (oh, and writing your thesis) - grad school is a veritable hamster wheel of rejections and failure.

The really difficult thing for me has been learning how to fail well; how not to take failing as something that's wrong with me, but to take the lessons I learn from it, pick myself up and try again.

DMing and the art of failure

One of the beautiful things about DMing is that you are a routine student in the art of failure.

Very few - if any - of your plans will go exactly the way you want them to. Your players (and the dice) will conspire to take your game off the rails and into uncharted territory faster than you can say "critical fail". It's not a great feeling when a roll that your entire table has been rooting for doesn't pan out and you're left to pick up the pieces (or worse, the body parts).

When this happens, it's important to think big-picture. What does this particular failure mean in the context of the larger narrative? Failure and moments of crisis need to have a part in truly great story-telling, especially in collaborative story-telling like a tabletop role playing game.

In a dice-driven game like DnD, both player failure and success should to have meaning. Characters might face consequences for that poor ability check, but the story moves forward anyway, and the characters can use that failure as a moment for growth.

Failures are gifts that help to shape future actions. And if the players have a supportive group playing with them, failures can guide some of the most engaging, poignant, and funny moments at the table.

Failing forward in the real world

Many of these same lessons in failure are true in real life.

A single mistake does not define your entire story (at least, it doesn't have to). Failures can be guideposts in the wider narrative you tell about your work in the world. And a good support system - at work as well as at home - is critical to providing a soft landing place where you can safely fail forward without landing on your face.

I still struggle with perfectionism and imposter syndrome. I probably always will. But through my role as a DM, I've learned that failure is not only expected and important... but it can also be surprisingly fun.