I’ve been playing tabletop RPG Dungeons & Dragons (5th edition) regularly for a couple of years now, with a small group of close friends. We started with one of our number running a big long campaign, then when we got to level 20 (and after I’d finally cajoled him into letting us fight the Tarrasque), the next started his big campaign. About half-way through the first, we took a small break to play the published adventure Dragonheist. During this second campaign it… fell to me to provide the interlude adventure.

Picture the scene: a man who has dedicated his life to spending years meticulously crafting scenarios hosting an infinitely-responsive adventure with only a week between sessions for planning.

, as the old saying goes.

Who Wants To Be Dungeon Master?

We played some 3.5e and 4e way back when we were in university, though the physicality and the larger group sizes meant we rarely got very far into a campaign before life got in the way. Back then, I spoke wistfully about maybe taking a turn at being DM for a little adventure, but ultimately I always had other projects on my mind, so it never happened.

Fast-forward ten-odd years and this thing called “the Internet” offered a new answer. We’ve been using roll20 to play virtually, and goodness me, do my rubbish mental arithmetic skills love that auto-dice-roller. When the pandemic hit, D&D at least didn’t change for us — we were spread across multiple cities anyway and well entrenched in online play.

I resisted the mantle of DM for some time, because honestly, the thought terrified me. I’m used to ruminating on plot points for days, for weeks, for years, and just generally working at my own pace. To be DM, you have to plan loosely and quickly: you have to plan enough to give your players something to aim for, but not so much that you’re ignoring their choices and their impact on the world. We play weekly, so after the initial burst of overall scene-setting and outlining, I’d have to wing it.

Though I have admit that I was also quite curious about the role. Would any of my experience writing and designing computer games be remotely transferrable to the living table-top, or would deployment of all those techniques fall flat? Would they call me out on all my inspirations? Would they laugh at my jokes?

The DMing bar had been set very high by the group, so there could be no half measures. I wouldn’t have been comfortable running an off-the-shelf Somebody Else’s Adventure, nor would I have been happy to cop out with an inconsequential one-shot dungeon crawl. It needed to be fresh and it needed to have some substance.

So I set my sights on building a low-level adventure, to keep the numbers and balance comprehensible to a mere mortal. I aimed to make it last 4-6 sessions; long enough for everyone to get their teeth into it and build to a (hopefully) satisfying climax, but not so long that my rickety planning would start to disintegrate and expose all the gaps. I also wanted space to do a mix of combat, wilderness travel and social encounters, to get the full breadth of the DM experience (and also give the player characters plenty of time to interact amongst themselves).

To reduce the risks as much as possible, I settled on the most classic of all conceits: I stuck them on an island. A jungle island (take a shot). Gathered up from their respective backstories to join a suspicious mission to this island, their ship is struck down by Mysterious Forces and — how convenient! — they are the only three survivors (or are they?). The rest was just making sure the thick jungle was just uninviting enough that they stuck to the very small number of paths between the landmarks on this mostly-uncharted island.

Thankfully, they went along with it, though I’m assuming more out of politeness than any cunning narrative orchestration on my part. Phew!

D&D World Editor

I bought Scrivener a while ago to use for my writing projects, and as a tool designed for storing and rearranging sporadic chunks of text, I found it ideal for managing all my campaign notes. Rather than chapters and scenes, each section was an encounter; either a description of an important piece of landscape, some notes about a specific character they would meet, or an actual battle. Scrivener lives on my very portable little laptop, which also meant I could have my materials on that screen to the side and roll20 on the main computer.

I went through the Monster Manual and copied out stat blocks for creatures I thought might populate each area, so that I’d have them to hand rather than needing to rake through the book every time. A few classics like the Ankheg went in unscathed, but for others, I simply took stat blocks that looked useful and “reskinned” them as the creatures I actually wanted. This seemed to work quite well: I got the balanced enemies for fair challenges from the book (and could use Kobold Fight Club to help plan the encounters), but got the flavour I wanted in play (i.e. dinosaurs; take a shot).

(I might have played more fast and loose with the stat blocks later on, because they kept wiping the floor with my encounters. For example, I had great fun giving the Hook Horror a powerful chest saw attack it could use once grappling a target, to turn it into Gigan (take a shot). The druid, who had run ahead and got grappled by surprise, did not enjoy this so much.)

Then I needed battle maps. The prevailing advice (backed up now by bitter experience) was to make battle maps outside roll20, and upload them as single flat background images. I could have scoured the internet for free maps, as there are loads of them, but you know what I’m like — I need things to be just right, and hey, I enjoy doing terrain work anyway. I heard a lot of good things so I decided to splash out on Dungeondraft, and I have to agree, it is very good. (I was apparently so effusive speaking about it to other RPG-playing colleagues at work that two of them immediately went out and bought it.)

The important thing is that Dungeondraft makes it quick to whip maps together. That means the hard part of planning a session is thinking what maps to make rather than actually making them — and it means you can make maps to match your scenario rather than having to shoehorn in found material. Maybe the maps I made weren’t as perfectly detailed as some you can find, but I’m comfortable that they conveyed my intent well enough, and Dungeondraft has a wealth of assets included to cover a huge swathe of medieval fantasy needs — and some recolouring and scaling can take you beyond that zone well enough for when they finally reach the crashed alien spacecraft (take a shot).

That’s not to say that I always succeeded in producing maps. I foolishly did not build the upper level of a fort and — yep — rather than being a non-space from whence a couple of reinforcements could descend, the players ended up going there. I had to scribble it straight into roll20 with box outlines… how embarrassing.

Having my notes on the second screen while running seemed like a good gambit, but I kept missing out on important parts anyway. In the intro, the players were supposed to get an advance in gold to prepare themselves for the mission… which I totally forgot about until they were almost out the door. They almost walked past the tavern in the deserted town because I forgot to call out a detail that would draw them to it. I totally missed the fact that my “demon” Warriors had improved +6 constitution saves rather than their straight +4 modifier. And so on.

Running combat was similarly forgetful. I’m so used to being a player, where I just watch out for my turn, take my actions and then sit back… So many times, I’d make a monster take its move, and then sit back… and realise that it was up to me to call the order of who came next! And half the time it was me again for another monster! Aieee!

Meanwhile, the other reason I sent the players to a mostly-uncharted island where everyone had disappeared was that I only had to plan out and act a small number of characters. Since I’d worked out what the characters knew rather than precise bits of dialogue, responding to the players’ queries actually seemed to go okay; though I still managed to miss big chunks of foreshadowing… But, eh, the players didn’t ask all the right questions, so that’s on them! … Okay, fine, that’s on me not telegraphing what questions might be the right ones. Many characters simply did not act suspiciously enough.

And now it’s over. Would I want to do it again?

Despite dropping in a few potential sequel hooks, hell no. Being Dungeon Master combines things I’m very comfortable with — world-building, writing, level design — with things that I find incredibly stressful — unpredictability, improvisation and split-second decisions. I have the profoundest respect for my friends who DM regularly and can put together and handle all of these pressures (or at least sustain the appearance of such for extended periods), but that just ain’t me. I can just about manage it for one character as a player, but doing it for the whole world is exhausting.

I suppose I’m glad that I’ve now been Dungeon Master once, ticked it off my bucket list so to speak, but I have no desire to repeat the experience. As for whether or not my campaign was even successful… You’ll have to ask the players that one.