How Dungeons and Dragons Helped my Software Development Career

August 9, 2019   //   Application Development Careers, ,

Dungeons and Dragons is having a moment. Once a guilty pleasure not to be discussed around non-gamers, people now stream their gaming sessions live and rack up millions of views.

D&D is featured prominently in the Netflix mega-hit Stranger Things and other popular shows such as The Big Bang Theory. Hollywood celebrities such as Vin Diesel, Joe Manganiello, Stephen Colbert, and even Matt Damon and Ben Affleck talk openly about their D&D roots. Somehow, miraculously, D&D has become, dare I say… cool!

This all got me thinking about my own experience and how D&D truly impacted my career.

A few decades ago, as I sat in a basement behind my homemade Dungeon Master’s screen glancing through tables of stats and rules that I had photocopied, cut out, and taped together, I would have never guessed that I was growing the backbone of a job running a large software development practice.

But I was.

The skills necessary to run a Dungeons and Dragons campaign, especially one starting in the 90s, are skills essential to my job today. So, let’s start at the beginning: come, join me with a tankard of ale at the inn, and let me regale you with glorious tales of adventure and woe!

First, I played in a few games run by friends and learned the basics. It was fun. It was really fun. But it seemed haphazard, choppy. I saw the potential for something epic. If only…if only there was a little more organization, a little more continuity.

You see, it’s not enough to have some good players and some creativity. That can make for a few good experiences, but it won’t lead to something that lasts. The same applies when you are building custom software – it’s not enough to have a few good ideas and a handful of talented developers. Those developers can probably deliver on one-off projects, but if you want to scale and be efficient enough to enable something epic, you need structure, organization, and leadership.

Business lessons learned from Dungeons and Dragons

I determined if I wanted to be a part of something that would last, something bigger everyone would want to be a part of and push all competition aside, I would need to get organized. I would need to plan. To that end, I created an eight-part story arc. I would take my players on a journey. They would invest in their characters because they would not just have an isolated good experience, but they would look forward to the next experience. I didn’t realize it at the time, but this was business 101: your first sale usually isn’t profitable – you need returning customers to really succeed.

The planning paid off. The gaming sessions were great. 8 hours, 10 hours, 12 hours would fly by like nothing and the crew would want to get together again the next day. Word began to spread – new players wanted to join. Little did I know I was learning networking and marketing skills. Friends of friends heard about it. I pulled in more of my friends, eventually joining two separate groups I was running into a single super-group.

I was forced to learn how to say no. Just as turning down a potential project because you don’t have the resources to do it right is something I had to come grips with – telling people I liked and wanted to hang out with, that we simply didn’t have room, was the right call. We were already playing a game designed for 4-6 people with 9+. If I added any more, everyone’s experience would be worse.

Things were going well. Those first 8 adventures turned into 20, then 30, and we kept playing. We semi-retired our first campaign (a “campaign” is basically a continuous story line you weave together through all the many scenarios you play through) and started a second one. My players and I got older, finished high school, and started moving in different directions: different schools, different towns, different careers. That’s where I really learned skills that would help me run projects end eventually large teams and a practice.

dungeons and dragons

Keeping the nerds on track with project management skills

Years into it, everyone still wanted to play, but gone were the days of being able to just make some (landline) phone calls and send a few pages, and suddenly get 8 people to show up for a 12-hour block of time. It required planning, coordination, and scheduling. I had to do the work and realized I wouldn’t succeed if I didn’t start getting more structured and using some tools.

At first, it was the most basic and essential of all project management tools: the list. I made a lot of lists: lists of possible dates, lists of players, lists of date conflicts. Also, lists of random monster encounters for all terrain types, lists of the noble houses (complete with coats of arms), lists of dwarven and elven currency denominations, lists of the various leaders of the Knights of Aar, lists of published adventures or magic items I wanted to use at some point… you get the idea…THE IDEA THAT I WAS SUPER COOL!

This was truly project management, and honestly, it was complicated project management. Every adventure required prep. Every basement gaming session required meeting management. Every adventure had a wrap up with action items and next steps – and all of this for groups of 8 to 12 people over the course of years. Scheduling also was a cornerstone of success – without deliberate, often difficult scheduling, there’s no way we could have regularly played through our twenties and into our thirties as everyone now had to juggle houses, families, and careers.

At first, this management was done with phone calls and paper lists, but it evolved with technology. Email became an invaluable tool, and my work and gaming life were soon feeding off each other, growing best practices for effective use of email.

When we started our 4th campaign (based on a premise of a world cursed to be a sort of divine graveyard littered with the husks of dead gods from many different worlds… AWESOME!), even email would no longer really suffice.

Much like when a project outgrows some of its original processes, we adapted and began communicating schedules via a dedicated campaign website. To this day I credit success at scheduling the staffing of dozens and dozens of project teams to lessons and insights gained while scheduling adventures for a dozen nerds.

Learning how to adapt to constant change

Another concept that D&D introduced to me was a constantly changing and evolving environment. If you are in a technology career only one thing is certain – the technology is going to change. The very rules of the game you base your decisions on are going to change. In D&D this takes the form of an ever-evolving set of rules or editions.

Currently, D&D is on its 5th “edition” since it was created in 1974 by Gary Gygax and Dave Arneson, but even within an edition new supplements containing new options, items, rules, and details are constantly released. I developed a lot of stuff for my early campaigns. I still have a lot of it: handwritten tables, amazing magical artifacts, characters, monsters and so on – all crafted with love, and of course, all really spectacular! All of it, every last bit of that work, was instantly invalidated when the next edition came out. Those things were the equivalent of the IP that we develop in the software world. It’s good stuff. It was well made. It took a lot of effort… and you must be comfortable with letting it go when the time comes. (For you gamers out there, we started with Second Edition AD&D in all its terrible glory with THAC0 and non-weapon proficiencies. Then we moved to 3rd and 3.5 and eventually Pathfinder.)

Here’s the thing. As much as I loved all that Second Edition material I created, in retrospect Second Edition was trash! It was awful as far as a rule system goes – full of imbalance and contradiction and loopholes. Similarly, in software development, as much as I loved programming character-based green screens, we had to move on. And then we had to move on from WinForms, and we’ll continue to have to move on, and likely at a faster pace. As a DM, I planned for, embraced, and even got excited for the release of the new supplements, options, and editions, which made accepting paradigm shifts in my career more manageable.

I could go on and on, but for now brave adventurer, we must conclude our tale. I think there’s something to it – a correlation between being a successful dungeon master and being a successful professional leader. One last little story to illustrate: I was talking with my boss about time off several years back because I was going to Gen Con, a huge gaming convention. This was a mentor, manager, and leader in our organization. He chuckled a bit, told me he went to Gen Con back when it was actually in Geneva, and then derided the current edition of D&D, mentioning how he still had the Red Box and 1st Edition was all you ever needed. I knew then, I was definitely working in the right place!

Aaron Selle leads the Application Development Practice at SWC. Though he has furloughed his Dungeon Master’s Screen for now, he currently keeps his geek heart beating playing Gloomhaven, and assures us he will drop more twenty-sided dice in the future.