Life and leadership lessons from Dungeons & Dragons

Last year I started playing Dungeons & Dragons for the first time. As a D&D newbie I was nervous. Would I have to wear a costume? I didn’t even know how the game was played.

For those new to Dungeons & Dragons, here’s how it works: a narrator (the dungeon master) reads out to a group of people descriptions of a place or scenario. The group decides what to do, and the narrator unfolds the story based on their decisions. At certain moments players roll dice to determine the outcome of a decision. It’s basically a free-form, collaborative Choose Your Own Adventure story.

At the same time I started playing D&D, I was transitioning into a new job as CEO of Kickstarter. I initially started playing to hang out with the Kickstarter team. Over time the game has become much more. Here are three things I’ve learned playing D&D.

1. Know who you are

Knowing and accepting who you are is the most important thing to do in D&D and life in general.

In D&D this is quite deliberate. When building a character you’re first asked to declare whether you are Lawful, Neutral, or Chaos. My group began by declaring ourselves Neutral, but events soon revealed a darker edge. After a particularly gruesome encounter, it was obvious: we were Chaos.

Accepting our Chaotic nature was a literal game-changer. Rather than debate how to respond to each situation, it was clear how to act. Once we knew who we were, there was often only one real course of action.

2. Know what you want

In our adventure we began hearing rumors of the Master, the root of evil in our world.

One day I made a proposal to the group. We would find the Master. We would pay tribute to him as his subjects. And then we would slay him and become the new Masters ourselves. We all agreed to this audacious plan, and everything about our game immediately changed.

D&D is typically about exploration. You search rooms, open doors, and explore terrain. Once we declared our mission, things took a different shape. We explored, but with a purpose.

We began to see anything that wouldn’t ultimately lead us to the Master as a distraction. We encountered countless corridors and mountains of treasure. We ignored all but those that seemed likely to lead us to the Master.

The impact of our focus was startling. Questions of tactics and strategy continued to arise, but we approached them with an obvious purpose. Once we decided who we were and what we wanted, it was clear what to do.

After much searching, we finally found the Master. We declared allegiance as planned, and soon found ourselves in battle. After a long and difficult fight, we were victorious. We took the Master’s seat.

3. Parlay first, fight second

When we started our quest, we would engage in battle as soon as we encountered an enemy. We won these battles but they were painstaking. We had to fight enemies one at a time. Our characters were weak and inexperienced. The risk of death was real.

Over time we began to take a different approach. We would first try to parlay with the enemies and convince them to help us or surrender. We used appeals, threats, and tricks to get them to lead us to the Master.

Parlaying had much bigger rewards than fighting. By parlaying we could impact an entire group of enemies, not just ones we physically fought. Soon we began every encounter with an attempted parlay. We would fight only if that failed.

Thankfully I don’t have any literal application of this lesson to my life, but it reminds me of how important it is to scale your actions. It’s satisfying to roll up your sleeves and try to fix every problem yourself, but big picture it isn’t sustainable. There’s just too much to do.

Instead, parlay by sharing the challenge with your team. Even if the efforts come up short, the team has gotten more experience, and your performance in the next challenge will be much improved.

I’ve come to see our Dungeons & Dragons quest as more than a battle with monsters and mazes. It’s been a test of character. The obstacles we faced gave our group purpose and helped define who we are.

Who are you? What do you want? These are the questions to answer. We can’t control events, but we control how we respond to them. Who knows? With a little bit of luck, you just might find yourself the new Master.

My D&D game. From left to right: John, Taylor, Luke, Liz & George

I wouldn’t have survived to learn these lessons without my brave compatriots. Thanks to Liz Cook, George Schmalz, Taylor Moore, and John Dimatos for their wits and wit. And thanks to our incredible dungeon master Luke Crane for guiding us on our quest.

I shared a draft of this essay with the group before posting. Liz responded with her perspective. Here’s her take:

Thinking about taking down the master/becoming the new master was both hilarious and undeniably the right move. It was also very risky — and I think that risk played an important role. It made staying on task feel even more crucial. We were aware of our scrappy first or maaaybe second level brigade and that feeling of being ill-prepared propelled us to stay on target…cause we had to. Don’t you think it could’ve felt different in circumstances where we came with higher levels or more powerful spells or just knowing what to expect? I also wonder if we felt brave because we didn’t feel like we had so much to lose yet. We hadn’t leveled up a number of times. Maybe our lack of experience made us less likely to fear what we had to lose. Maybe it was the fact that we weren’t safe peddling around the caves and could die at any time regardless? I don’t think any of this takes away from our glory or bravery and certainly not our determination to reach our goal however.
Some of my all time favorite moments in the game have been the parlay encounters. A big part of why I enjoy them is the human-ness that it brings to our D&D world. Fighting is definitely fun but even when Luke does such an amazing job painting the battle scene, it can still feel very anonymous to me. A parlay invites emotion, spontaneity, and an unpredictability in outcome that just delights me to no end. This holds true in real life as well.

I couldn’t agree more.

Thanks for reading.