Level Up Your Career with Dungeons & Dragons

“Dungeons & Dragons” tends to conjure up images of a few pimply nerds hunched around a table in a dark basement, arguing over who gets to wear the enchanted cape they just found after plundering an accursed castle.

But you couldn’t be more wrong. Dungeons & Dragons players actually come from all walks of life. Definitively cool celebrities like Tim Duncan and Vin Diesel love to explore dungeons and fight dragons when they’re not blocking shots or driving fast cars.

What most people don’t realize is that Dungeons & Dragons is actually a complex game of social interaction and chance that harnesses one of the oldest professions in the world (no, not that one): storytelling.

Humans love to tell stories. Look around you. Chances are you’ll find yourself within sight of some sort of storytelling medium. Maybe it’s a pile of books, shelves lined with movies or video games, or—at the very least—the device you’re reading this on.

And stories aren’t just meant to entertain. Before humanity figured out how to write things down, storytelling was the only way to preserve knowledge for the next generation. It was a vital step in getting us out of caves and into high-rise apartments.

Now that we know D&D is built off our innate desire to tell stories, plus the fact that super awesome cool people play it, it doesn’t look so nerdy now, huh?

Okay… so maybe it’s still “nerdy” in the traditional sense, but that doesn’t matter.

What I care about is how to take a form of entertainment that I love and leveraging to improve myself in other areas of my life. What I’ve found is that D&D is an excellent teaching tool for the real world, especially in a work environment.

In this post, I’m going to spell out some of these benefits and provide exercises that you can try in your own life to level up your career.

Let’s get started!

Learn to Work as a Team

Dungeons & Dragons is a team-based game. It’s meant to be played by multiple people. Sure, you can try to run off as a lone adventurer, but most the time you’ll end up dead.

To succeed in the world of Dungeons & Dragons, you must learn to work as a team.

Know what else requires teamwork? That’s right—almost every job ever!

In D&D, a group of adventurers with disparate skills join together to accomplish some goal, such as slaying a dragon that has been terrorizing a local town. You might be a spell-flinging wizard, a sword-swinging fighter, or maybe a shield-wielding paladin, and it’s up to you to use your unique skills to best help the group.

The same thing happens in the workplace—a group of people with disparate skill sets join together to accomplish some goal. From my own experience working in the world of technology, I see Cloud ninjas, C# giants, and JavaScript wizards who all must cooperate to deliver an effective technical solution to a client.

By participating in a game of Dungeons & Dragons you quickly learn that you can’t do it all. Those who ignore their team will swiftly meet a gruesome end (often to the party’s relief—selfish players are the worst).

The adventuring parties that become the stuff of legend are those who take notice of their team’s collective abilities and use that knowledge to overcome any obstacle.

The same can be seen at work. You can’t do everything yourself. And that’s okay. Everyone has their own specialized set of skills and their own weaknesses as well.

If we learn to recognize the strengths and weaknesses of our teammates (and ourselves) and use that knowledge effectively, we can become a high functioning unit capable of slaying the toughest of workplace dragons.

Quest 1: Offer to help a teammate by teaching them more about something you do well. Then have them teach you something that they do well.

Reward: 100 XP and a Shroud of Teamwork

Learn to Improvise

Role playing video games like Skyrim or World of Warcraft are heavily based off of tabletop RPGs like Dungeons & Dragons. However, those video games limit the options available to a player. If the game hasn’t been programmed to allow you to convince a troll that he should take up knitting instead of ambushing travelers, you simply can’t do it.

But in the world of D&D, the only limit is your imagination. You can literally do whatever you want, which is what makes the game so damn fun.

Want to avoid fighting the hulking red dragon and instead appease it with compliments or treasure? Give it a go!

Have you always wanted to be a politician? Try campaigning for mayor in the local town you just saved from a pack of ravaging werewolves!

Feel like stabbing your whole party in the back and joining the evil vampire in his quest for world domination? You can certainly try (although your friends will probably hate you).

Obviously, you’re improvisation is more likely to succeed when you play to your strengths. It is much harder for an anti-social elf to become mayor if she isn’t able to delivery a rousing speech to rally supporters to her campaign.

This kind of experimentation in Dungeons and Dragons teaches you that there is always more than one way to do something. The same rings true in your career.

As you are faced with a new challenge at work, think about all the skills you have at your disposal. Choose the one that you feel will help you succeed, and give it a go! If you absolutely nail it, you’ve found a great new way to succeed. If it goes alright, you’ll know how to do better next time. And if you flat out fail, you’ve learned a valuable lesson that can be applied to future challenges.

By experimenting and improvising at work, you may stumble onto something that makes you more effective and a better employee.

Quest 2: Think of a new way to finish a common task at work and try out your idea.

Reward: 200 XP and Boots of Dexterity

Learn to Ask Questions

Because the entirety of Dungeons & Dragons takes place within the imaginations of the players, there are no fancy graphics to convey what the world actually looks like.

This means everybody has their own version of “reality” floating around in their heads.

This is where the Dungeon Master comes into play. He or she is the referee of the game and the eyes and ears of the players.

One of the most important jobs of a good Dungeon Master is to provide a description of where you are. For example, upon returning from a quest given to you by a local ruler, your DM might say something like this:

As you walk back into town dragging the hulking carcass of the dead dragon in your wagon, the townsfolk cheer. It seems the entire city has come out to celebrate the death of Faranguard, the Scourge of the North, and they’re packing the streets hoping to get a mere glimpse of both the dragon and the heroes who slayed it. As you walk through the town, people periodically step out of the crowd and hand you gifts.

One of the players who might be controlling an alcoholic fighter named Camton might turn to the DM and ask “Were any of the gifts wine or ale?” The DM could respond with a yes, in which case Camton would immediately down an entire bottle. He really needed a drink after that fight.

We often encounter the same sort of ambiguity at work. Sure, we probably have a good sense of the general direction and goals of a project, but the details can get a little fuzzy. To paint a clear picture, we rely on asking questions to our real-life Dungeon Masters. Unlike the game which only has one, you probably have multiple DMs at work, ranging from stakeholders to your boss to a knowledgeable teammate.

You need to ask thoughtful questions to extract the best information from those around you. As you ask these questions, you’ll learn which questions matter more and the best way in which to ask them. With more practice, it will become second nature and you’ll be a valuable asset that always knows just the right question to throw out there to move your team forward.

Quest 3: Find something at work you’d like to know more about and start asking questions that help expand your knowledge.

Reward: 500 XP and Goggles of Darkvision

Learn to Embrace Failure

In Dungeons & Dragons, some things come down to an unlucky roll of the dice. Even the best of heroes will occasionally role a “Natural 1,” which is an automatic failure when you roll a 1 on your die. Given that you typically roll a 20 sided die—also known as a d20—you’ll experience this failure about five percent of the time.

Sometimes these failures are the best part of the game. Maybe you shoot a fireball at a skeleton, but roll a 1 and instead magically bestow it with a flaming sword that causes twice the damage against your best friend standing nearby. Or you try to hurdle a short wall but trip and face plant into a pile of troll dung.

We’re not immune to failure in real life either. It’s an inevitability, and the best we can do is learn from it. When you fail, figure out what you did wrong, and work to do better next time. The most successful people in life are the ones who use their failures to improve. And while failure can sting in the moment, you might be laughing at the same situation a year down the road, realizing just how much you learned from screwing up.

I know I have had plenty of failures—some of which felt like the end of the world. I try to learn from them and do just a little bit better the next time around. So far, I’m feel like I’m doing a bang up job and I hope to keep learning from any future failures that will definitely come my way.

Also, when others around you occasionally fail, help them realize it’s an opportunity to learn and grow. A team that helps one another learn from their failures is much more effective than those who don’t.

Quest 4: Think of the last time you failed. What went wrong? How will you learn from that experience?

Reward: 1000 XP and a Helm of Charisma!

Quest Log Review

Everybody has a quest log filled with hundreds of things we could be doing. Those quests range from the profound to the mundane, and our priorities drive which of them we devote our attention to. Some are more rewarding than others. Some are fun but bring no great value. There are always more quests to find, more towns to save, more disasters to avert.

We all have our own dragons to fight. They’re all unique and special and wonderful. They’re what makes us tick and what makes us unique.

I encourage you to give these quests a try. They’ve worked well enough for me, and I hope they do the same for you.

Let’s do a quick review so these don’t get lost in our quest log:

  1. Offer to help a teammate by teaching them more about something you do well. Then have them teach you something that they do well.
  2. Think of a new way to finish a common task at work and try out your idea.
  3. Find something at work you’d like to know more about and start asking questions.
  4. Think of the last time you failed. What went wrong? How will you learn from that experience?

Once you’ve completed these quests, you’ll have leveled up!

You’ll be a more effective teammate, using creativity in problem solving all while expanding your skill set.

And maybe most importantly of all, you’ll have learned that what doesn’t kill you makes you stronger as you learn from failure and become the adventurer you were always meant to be.

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