How I rolled initiative into D&D

I could say that I first played Dungeons & Dragons back in 2018, at my previous job.

I could also argue that it wasn't until 2020 that I really began playing for real –as a Dungeon Master– for some colleagues from my current work, as part of our plans to cope with the quarantine.

But, I must admit to have been hooked by D&D since 2017. At least passively.

Dice rolled on a Dungeons & Dragons session. Players were not too happy with me stopping the game for a picture.
Photo by James Pond / Unsplash

Once upon a time... in Fantasy Land

The story of how I got into D&D is an interesting one, I think. I vaguely knew of the existence of the game, first when I was a kid and then at the university.

Funnily enough, when I was a kid, I used to enjoy very much inventing my own board-games and also play make-believe; I'm pretty sure I'd have enjoyed D&D a lot if I had known it better at the time.

Fast-forward several years into the future and, in 2015, I moved to the UK. At that time, I kept hearing about a game called The Witcher 3. I had no clue about it. One day, I watched someone play the intro of the Blood & Wine expansion – my first time watching the game at all. It looked gorgeous, I was in love.

The Witcher 3: Blood & Wine / CD Projekt Red

After that, I bought the games and tried to play them in release order. The first game one was so weird and outdated that it turned me off after a while. It wasn't until a year later that I decided to give it a try once more. The Witcher 1 ended up being enjoyable, despite its flaws. Witcher 2, even though it was tougher, was a huge step-up; I enjoyed it immensely. Witcher 3 was just... wow.

At that time, I also got into Gwent, a collectible card game based on the mini-game from the third entry of the Witcher series. I only played the beta, as the updates kept bringing heavy changes to the game that required some relearning. It was at this point that I began to think of about how I never got into Magic: The Gathering. I had played TCGs before, in times bygone; mainly, Yu-Gi-Oh! and Pokémon. Yet, I only knew of people that played Magic.

Now, before continuing, there's another thing that led me to D&D, and it also had to do with the Witcher: CD Projekt Red. I read that they were working on Cyberpunk 2077; this was at about the time I was discovering one of my favourite genres: cyberpunk. My hunger for more cyberpunk led me to Cyberpunk 2020, another famed table-top role-playing game and precursor to CDPR's game. With all of these ingredients in hand, it isn't too wild to see how I landed on D&D.

What's the worst that could happen?

It's all downhill from here.

The dawn of an era

I can assure with all confidence that: if initially I was just merely interested, what really sealed the deal for me were the videos from Matt Colville. Whereas most D&D videos on the internet were either basic or boring, Matt's were engaging. There are no words that can describe the level of investment I had with his videos. I could watch them for hours. And once they were over, I would re-watch them again and again. I couldn't count the days until a new video would come out.

I was like a sponge, absorbing as much as I could, feeling the same joy as my younger self, playing make-belief. This was it, I had found something that just made sense and really resonated with me.

Photo by Anna Gru / Unsplash

It didn't take long until I bought the D&D Starter Set –which, to this day, I haven't used– and, after a while, I bought the three main core books: the Player's Guide, Dungeon Master's Guide and the Monster Manual.

At this point, I had the books but I missed a group to play with. None of my closest friends were into D&D and my shyness made it difficult for me to ask others at work.

After a year or so of passively engaging with the game, I decided to write to the gamers e-mail listing at work, which people used to organise board game sessions. Some people replied interested in playing and, luckily, someone offered himself as a DM. We only played a few times, though, since we were a few months shy of the release of our project. Work was too taxing for any of us to have enough free time and energy to play.

A few months later, I moved to France and changed work. There, I twice proposed to play some good old Donjons et Dragons. This time, however, no one was really into being the DM.

My resistance to fulfilling that role was mainly due to my (practical) inexperience with the rules; I didn't want others to have a bad time and stop playing because of me. And so, 2019 passed, we didn't play and my interest in the game faded into the background.

In 2020, due to the quarantine, we wanted to find some way to connect despite working remotely. This time I accepted the challenge and decided to don the mantle of DM.

My first D&D campaign

I'll probably dedicate a whole post about this, but here's the gist.

I made a survey using Google Forms, asking how many were interested in playing. Surprisingly, 8 people replied. In the form, I also asked a few questions about each participant's familiarity with the game (5th Edition, in particular). Other questions included what type of experience they were looking for and how their interests were divided amongst the three pillars of adventure: combat, social interaction and exploration.

I had players. Too many in fact. How was I supposed to run a game for 8 people? This was my first time as a DM and, even if it weren't, playing with a party of 8 can become a daunting matter. So many players can slow down the game, leading to boredom and disengagement. Luckily, I remember one of the videos from Matt Colville, where he discusses a style of game called The West Marches.

The gist of a West Marches type of game is that the big group is just a pool of potential player and only a handful of them participate on each session. Instead of following an overarching plot story, the players are then given free rein to choose their adventures and when to play. This way, they can join those that interest them or fit into their schedule.

It seemed like the ideal strategy for us!

However, as one should have had expected, some people didn't end up joining. From a total of 8 players, we went down to a party of recurring 4 to 5 players. This was still great, we could play after all, but it also meant that we could no longer reap the main benefit of a West Marches game.

Now, either we had enough quorum to play or we didn't. This meant that we had to just accept that, if we played on some days of the week, we'd have to imagine reasons why the fifth member couldn't join the adventure. The reason we came up with was that they got too drunk with goblin ale and had to stay back, resting.

I must admit that being a DM can feel scary and overwhelming; in my case, I felt as if I had this immense pressure on my shoulders. What if people didn't like my setting or my style? Do I even have a style at all?

I spent the first weeks trying to prepare a killer campaign, with maps and a background to the world. For the maps, I was struggling to choose between two tools. One was online and required a monthly subscription; the other one was a one-time purchase. I ended up trying just one month of the online tool. While at first the map creation felt incredible, I realised the immense work it represented, so I just didn't continue after a while.

Lore-wise, I also felt a lot a pressure to come up with something interesting enough for the players. I didn't have enough time and trying to do this at the last minute was exhausting. I knew that I wanted something compatible with the style of campaign I meant to run, so I came up with The League of Extraordinary Gentlefolk. Players would be part of a multi-class guild that would take on missions all over the continent.

D&D Beyond
An official digital toolset for Fifth Edition (5e) Dungeons & Dragons (D&D).

We used D&D Beyond to manage the characters and consult the rules.

I also wanted to use maps, so players could have a physical presence in the world, instead of relying solely on the theatre of the mind. For this, we used Roll20.

Finally, in order to communicate, we used Discord to video-chat and stream the map. Plus, we also made use of a bot, Avrae, to run most of our rolls. I decided not to use Avrae to also keep track of combat, since I found it a bit more tedious than to do so via D&D Beyond.

Despite all my fears, we ended up playing for a few months, until we just stopped.


We stopped playing towards the end of the year and started a temporary campaign using Necrotic Gnome's Old-School Essential, a back-to-basics retro-clone of the 1981 Basic/Expert rules for D&D. This time around, I participated as a player!

I picked a premade character: Swan, the Neutral Elf.

Swan, the Neutral Elf / Necrotic Gnome

Swan had a short life in our adventure, with a lifespan merely 3 sessions long.

With only 3 starting hit points, he managed to survive being attacked by an evil faun (1HP shy from dying!), read a scroll that turned him into Tom Thumb for a few hours, swapped personality with another PC, convinced some gnomes that our party was a termite extermination agency, adopted a rat and named it Pinocchio, lost it a few minutes later and ended up being mind controlled by an evil tree, until finally put down by the rest of the team.

I reckon my main takeaway from this experience is how different are the roles of DM and players. As a DM you usually have answers, you know what's needed to move the plot forward; its difficulty resides in being able to react and adapt to whatever the players come up with. Being a player can be exhausting for different reasons; you don't have the big picture and it can be frustrating to guess what the DM is expecting from you as players. Still, I find both enjoying and rewarding in their own way.

The future

Lately I have been interested in playing other tabletop role-playing games (TTRPG), mainly Call of Cthulhu, Cyberpunk, Alien, Mouse Guard and Traveller.

I would be lying if I said that running the game is no longer a daunting task. Yet, I only wish I could continue doing it; the only way to get better and more comfortable is by practising those muscles.

My journey so far has been one of ups and down, filled with a lot of daydreaming. I can only hope that the future brings me more of this hobby that I have learnt to love deeply.

♪ Gloria, gloria perpetua ♫

P.S. I have checked and it turns out that July 4, 2017 is the day I first searched for D&D content in YouTube; to be precise, it was this video from WASD20. I guess that makes it my D&D birthday!