Monster of the Week: The Dungeon Master

Evil Dungeon Master

(Or substitute writer, game designer, director, murder mystery dinner theatre master of ceremonies, cat, etc…)

We’ve all been there.

Despite the title, I’m not just talking about Dungeons and Dragons. Whether it was a game, a book, a movie, or what-have-you, we all know the feeling of a ruthless plot twist.

At worst, you’ve thrown your hands up. “This isn’t fair,” you’ve said. “I quit.”

At best, you might have said something like this: “You bastard! You clever, awful bastard!” Then, quietly, after the rage has settled:

“Then what?”

I can’t tell you what a delight it is to be on the receiving end of that possibly begrudging, probably masochistic “then what.” It’s something you have to experience for yourself.


Well, you budding monstrosity, you! Let’s get a quick definition out of the way first: what’s a dungeon master?

Dungeon Master originates from Dungeons and Dragons, and if you haven’t played before, you might not realize that there are two different types of players needed for a game. It’s half improv, half dice-rolling board game, and it can get out of hand pretty fast if you don’t have somebody to moderate. (Even if you do!) The Dungeon Master is that moderator.

Think of it like this: if you’re a regular player, you fit into the role of one character. You’re the hero in a video game. Everything that the computer supplies—enemies, story, your weapons, the world you’re exploring—that’s the Dungeon Master’s job.

The Dungeon Master is writer, director, cinematographer, technical director, and the actor behind every single bit part, all rolled into one. At heart, the Dungeon Master is a storyteller.

So asking what makes a good DM is asking what makes a good storyteller.

Answer: a whole big can of worms!

Uh, no, I don’t mean that possessing a can of worms makes you good at storytelling, I mean that question is a big can of worms. Ew, no. Put that away. Where did you even get that?

Anyway, becoming a good storyteller is a lifelong journey. You won’t find the answer in one blog post. And I don’t have that answer, by the way—it’s a journey I’m still walking and hope to be on for a long time.

So let’s  stick to the first few steps.


It’s really true, though! The first step to being really good at something is being really bad at it. But the second step is to recognize how you are bad at it—and find the tools to start fixing it.

So let’s talk about those monster DMs.

A monstrous Dungeon Master takes things just a little too far. The game is too hard. It crosses that thin threshold between “fun and challenging!” and “frustrating and impossible, fuck this, let’s just play Yahtzee and also we’re no longer speaking.”

A lot of us stumble across that threshold by accident when we’re just starting out. But, unfortunately, some DMs trample over it on purpose. They’re the ones riding in a chariot driven by hell-goats and cackling with vicious glee.

They think the game is DM vs. player. Author vs. reader, or author vs. character.

You know what? It is—but they forget the important part. You need to remember that this is a role you step into for only a tiny fraction of the time.

Your overall goal, as a storyteller of any kind, is to guide your audience through the story. When you’re running a roleplaying game, it’s obvious that the audience participates in the story because they are the characters. When you’re an actor reading out scripted lines on a stage, it’s a little less obvious, but it’s still there.

When you’re a writer at a keyboard, it can feel very far away.

But they’re going to experience your story whether you’re there to witness it or not. You need to learn to guide that experience.

Sometimes that’s gentle prods. Sometimes it means taking off the kid gloves.

When the gloves come off—remember your ultimate goal. If that goal is 100% audience suffering and no enjoyment for anyone but yourself—if that goal is to win the storytelling experience by defeating the audience, ha ha, those losers, look at how much better I am at this game!— then, uh, maybe you shouldn’t be doing this?

You need high points to accentuate the lows, and vice-versa. Bad moments can be part of an overall positive experience. It’s a balance, and it takes skill to master.

So when you wind up in a game with a bad Dungeon Master—whether you’re the player or you fucked up and now you are the bad DM—study. Learn. Look at what points are too much, where you need some levity. Where is a challenge rewarding? Where is it just grueling?

Where do you lose them?

Because that’s what matters in the end: it’s about trust. Once you’ve got that, you can get away with a lot. But you have to put in the work first.

So get cracking.

Prompt: If you’re a writer and you’ve never tried running a roleplaying game, it can be a fantastic learning experience. Grab some friends, find players at a local game shop or online, or check out some roleplaying videos and podcasts. Have fun!

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