When I was your age, television was called books.

-The Grandfather, The Princess Bride (1987)

I am no authority on Dungeons and Dragons. I’ve played a ton of different role playing games, but they have mostly been of the digital variety. I grew up in the age of Zelda, of Final Fantasy and Chrono Trigger. My first formal introduction to tabletop RPGs was a relatively forced encounter with Vampire: The Masquerade at the age of twelve, which lasted exactly one session. I was gung-ho for session two, but our GM was a friend’s mother’s boyfriend, and I don’t know if they broke up or what but we suddenly no longer had a GM.

After that, the closest I got to tabletop again was Planescape: Torment, a TSR-sponsored D&D vehicle, and what is in my opinion one of the most underrated computer games ever made. (Don’t believe me? Check it out for yourself.) It introduced me to key D&D concepts like the six basic stats, alignment, factions, and spell slots, and it did so in an unobtrusive way by building a story around standard D&D mechanics within the Planescape setting.

So how the heck did I become a Dungeon Master?

My day job for the last decade has been in IT, and like the cobbler’s kids with no shoes I find the technology in my life in a constant state of disrepair. As I type this, I have three computers at my desk, and the only one with any real power in it belongs to my employer. As the computer games I enjoyed became too sophisticated for my technology to handle, and our budget didn’t allow for new computers, I was forced to either find something else to scratch the gaming itch, or keep replaying the same older games over and over. #FirstWorldProblems. This coincided with a time in my life when I was looking for new ways to work on my writing skills, specifically around world building – I had ideas that needed to exist in complex, fully-formed worlds, and I’d never done that before. That, in turn, coincided with a coworker of mine talking about how he missed playing D&D, and wanted to start playing again. And all of that coincided with my having watched hours of Critical Role.

It takes a very specific temperament to be a Dungeon Master. You have to be creative, patient, excited about what you make while completely willing to throw it all away if your players choose not to follow it, able to think on your feet, roll with the punches and still be able to tell a great story the whole time, and on top of all that you need to know the rules well enough to break them effectively. I, the socially-awkward introvert I am, asked my coworker if he’d like to start up a game. Thus began my first foray into actually really for-realsies playing Dungeons and Dtagons, and guess what? I’m steering the ship.

No pressure.


I bought the 5th Edition Player’s Handbook (PHB), the Dungeon Master’s Guide (DMG), the Monster Manual (MM), and a Chessex 7-dice set, and began my cram session. I built character after character from scratch, just so I could see how the different stats interconnected during the character generation process. I started studying spells, then realized there are hundreds of them and decided to stop studying spells until I know they’re going to be used. I built NPCs from scratch.

I then spent weeks building a campaign. It was perfect. I had historical character interactions, a crazy wizard arch-nemesis, a world map I made from scratch, character handouts for each player…it was glorious.

Our game lasted one session.

You remember that underrated computer game I mentioned, Planescape: Torment? It starts by throwing you in the middle of a situation with no information about how you got there. I thought that was such a bold choice – so, naturally, I did the same thing. I mean, it’s based on D&D rules, that must stand for something, right? Turns out, that’s a terrible way to start a D&D campaign. Add to that the fact that of our party, only one person – one! – had every played D&D before, and I’m pretty sure we were doomed to fail.

I moved a thousand miles away and found a group of awesome people who are excited to play – they’re D&D novices too, but avid gamers, both digitally and IRL. Not wanting all that prep from my failed campaign to go to waste, I reworked it around the new character’s backstories, made a few modifications from the mistakes I made, and dove in again. After our first session, which lasted something like 7 hours, I was exhausted in that good way like after you exercise, we talked about the session frequently for weeks, and we planned for another one about a month out. And that’s where we are today.

How the heck did I become a Dungeon Master? Sheer force of will. I wanted to be one, so I did everything I could to not just become one, but become a really good one. People might give me crap about street cred or some such nonsense for my relative lack of inexperience, but I don’t care about having street cred. All I know is we have a blast.