Roll for Inspiration: Creative Lessons from a Dungeon Master

Marc Yates
Wayfair | Creative Copy
5 min readDec 7, 2021
Illustration by Abdulhakim Barkoumi

After days of fighting their way through pitch-black subterranean labyrinths, our band of heroes have finally found what they’ve been looking for. Four kidnapped children sit shackled, frozen in fear and in desperate need of rescue from this grim scene. The master of this underground fortress — a half-troll, half-giant slave trader — is in the process of selling them to an evil denizen of the Underdark.

The heroes are battered, bruised, exhausted. They arrived here via an abandoned gnome city that’s been overrun with monsters since a magical disease wiped out its population 75 years ago, and they’ve been beaten black and blue by the half-troll’s heavily armoured hobgoblin guards. They step into the chamber, and hear the clanking of armour as more hobgoblins raise their weapons to attack. What will they do now?

This is pretty much a standard Tuesday evening for me since some friends and I started playing Dungeons & Dragons. For those of you who aren’t familiar, D&D is a Tabletop Roleplaying Game. Using nothing but pens, paper, some dice and our imaginations, we sit around a table as a group and tell stories together. The players create characters who save the day, most of the time at least, and I’m the Dungeon Master. I create the world, rough storyline and obstacles for the players to heroically overcome.

A few months into our adventure, I realise that playing D&D is more than just an excuse for mid-week drinking and nerding-out with friends. It’s teaching me things about writing, and the kind of creative environment I thrive in. Here’s what I’ve learned so far.

Lesson 1: Yes, And

At its core, D&D is about improvisation, the first rule of which is to respond to everything with ‘yes, and’. This is a great attitude for a creative team to have. The creative process isn’t about being right all the time, it’s about keeping the ideas flowing. I’ve worked on a few ‘yes, and’ teams in my time, and I can say with confidence that the work they produce is always superior.

The fact is, there’s always, always a better idea. So saying ‘yes’ in a brainstorming session despite your doubts doesn’t mean you’ll settle on a bad idea, it means that the better idea is more likely to come forward. More importantly, colleagues who might think twice about sharing an idea after receiving a negative response will instead stay engaged in the process.

The hobgoblins make their advance, the tension is rising. Lagganlia, a 355-year-old gnome and retired champion archer, aims an arrow squarely at the big boss. Blorg, a greasy half-orc druid who stinks of his swampy home, readies his magical thorn whip to try and take out the remaining guards. And Dharakkas, the mysterious rapier-wielding rogue, ducks behind a pillar to prepare a sneak attack while he drinks his last healing potion. This is going to be a tough fight, but they’re ready for it.

Lesson 2: Collaboration is Powerful Stuff

Our heroes need to work together to save the day, and they need to work with the Dungeon Master to tell this epic story — just as creatives need to work together and with their stakeholders to produce great, effective work.

Writing can be a solitary activity. Some writers like having full ownership of their output, and others work better in teams. While I value time alone to think, for me magic happens when I collaborate with others. Whether it’s with another writer, a designer or even a project manager, someone else will always make me see a brief in a different light, helping me identify new creative paths to take.

Illustration by Abdulhakim Barkoumi

The fight is on, our heroes appear to have the upper hand. Suddenly, a sound that is at once a crack, a scream and a rush of air rips through the chamber: a Beholder has teleported into the room. It hovers above the ground, a fleshy ball with a large eye and several smaller eyes on snake-like stalks protruding from its body. Even the half-troll looks frightened in the face of this madness. “Oh…my God,” Dharakkas says under his breath. The way he says it leaves no doubt in the other players’ minds — they’re face-to-face with a legendary aberration that could kill them all without even blinking. How on earth are they going to rescue these kids now?

Lesson 3: The Rule of Cool

Learning how to play Dungeons and Dragons is famously difficult because the rulebooks run into hundreds of pages. On each turn they take, a player has several parameters to operate within — much like a copywriter navigating best practices, consumer insights, character counts and grammar. But when it comes down to it and you’re in the throes of battle with your friends, or writing creative copy, one rule reigns supreme: The Rule of Cool.

If an idea is really cool, the rules as written can and should be nudged aside in favour of doing something great. I truly believe that all the best pieces of creative advertising and marketing have employed the rule of cool, where a creative team will present a great idea because it’s great — rules, parameters and best practices be damned. OK, ‘rules be damned’ is maybe a step too far, but I encourage you to embrace the rule of cool — you might just wow a stakeholder into running with your great, rule-bending idea.

The Beholder turns its terrible eye towards the half-troll and roars: “Not this one you fool! He’s too important!” Its tentacle-like eyestalks wrap around one of the children, and there’s a deafening sound as, with the child, it teleports out of the room. No one saw this coming. The plot just thickened massively, and my players, ready to take their victory after dispatching the hobgoblins, enter into frenzied debate. Do they rescue the remaining three and find the other one later? Do they kill the half-troll or interrogate him? They’re freaking out. I’m having a great night.

Lesson 4: Drop Your Ego

The first rule of being a Dungeon Master is that no matter how much you prepare, players will find solutions to situations that you never thought of. The story will go quickly off the rails, time you spent preparing will be wasted, and it will be awesome. In many ways this is true of life and work, so why not embrace it? Whether you’re brainstorming, writing copy, or playing Dungeons & Dragons with your friends: leave your ego at the door. There are no winners or losers, you’re not here to be right all the time, you’re here to do something really cool and creative — together.

If you, foster a supportive, encouraging environment, work as a team and apply the rule of cool when you need it, then I really think that the next big project (or evil half-troll) will be no match for you. As for our heroes and that Beholder, it didn’t notice them this time. Or at least, they don’t think it did.

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