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10 Life and Business Lessons We’ve Learned From Dungeons and Dragons

by . June 3rd, 2014

DnD isn’t Just Fun – It’s Downright Educational. Entreps Take Note.

If you’re not too familiar with Dungeon’s and Dragons, it’s best to vicariously take the role of pre-fame James Franco as Daniel Desario, from the highly influential show Freaks and Geeks:


Since it was introduced in the 70’s Dungeons and Dragons has had an undeserved rep as THE GAME for the socially-inept. Which is surprising, considering that socialization and teamwork are innate aspects of the game.

Here are just a few things we’ve learned from Dungeons and Dragons:

10.) Treat the Dungeon Master With Kindness.

The Dungeon Master should be given due reverence. Even if they don’t deserve it. While supposedly impartial, nearly everyone knows that some DM’s are fairer than others, and all of them can make your game more difficult than it should be.

Antagonizing someone you need – regardless of whether or not their position is inferior or superior to yours – is sure to ruin your day. Don’t antagonize clients or contractors unless you know for sure you have something to fall back on.

Whether at the gaming table or the negotiation table, diplomacy always has a place.

9.) Everyone Wants to Slay Monsters. You Should Know Better.


L. Elmore Ancient Red

L. Elmore Ancient-Red

Slaying monsters and taking their treasure is a central part of the game. However, there are plenty of times where outsmarting monsters or even cooperating with them is the way to go.

Even before Sun Tzu compiled the Art of War, it’s been clear that direct confrontation isn’t always desirable. In fact, to be able to succeed with wits and diplomacy is the mark of a true master of the game.

While you’ll still need to prepare for direct confrontation if it happens, it’s always best for any venture to explore alternatives to conflict if they can.

8.) Learn of the Monster You’re About to Face.

First Edition Advanced Dungeons and Dragons Monster Manual (1978)
First Edition Advanced Dungeons and Dragons Monster Manual 1978

A little preparation goes a long way. You’re liable to get your whole party killed if you had the wrong spells ready when it came time to fight those kobolds.

Knowing the specific strengths and weaknesses of specific monsters can help you prepare the right spells, weapons, and potions and give you a much better chance of success. Much better than just hoping for the dice to roll in your favor.You can see where this is going.

The prepared will succeed consistently, whereas the unprepared never can.

7.) Everyone Wants Booty.



Not that kind of booty, you silly halfling. The promise of interesting rewards is the main reason DnD can get so addictive. Most of us just want to see what treasures lie around the corner. Will it be gold? Gems? A unique weapon?

We’re all motivated by something. You can’t convince talented people to come work with you if there’s nothing in it for them. You can’t sell to clients effectively if you don’t understand what they want.

Understanding what it is that motivates you and other people is essential not just for business, but for life as well. When you know what drives yourself and other people, it becomes far easier to put your efforts where they matter most.

6.) It’s Impossible to Succeed Without the Right Party.


You won’t ever get far with a party that’s all fighters, or all mages. You’ll need rogues, druids, thieves and a whole assortment of different race and character types to make it through your quests in one piece.

Each party will always need someone to handle the arcane, sneaky, and brute force departments. While jacks of all trades can be handy, few are able to master any single thing better than a dedicated specialist.

If you work alone, you might find it better to outsource or contract some of the more challenging aspects of your life – such as your taxes, or legal concerns for instance (if you aren’t lawyers or accountants yourselves).

5.) Unique Weapons > Big Weapons



DND Weapons 3.5Ed

A unique weapon or artifact will almost always give your characters an edge over the generic iron fielded by every footman and goblin from here to Krynn.  Unique items let you do things better than run-of-the mill characters and monsters and also provide far more color to your party’s narrative.

Unique selling points and unique tools are the things that define businesses best. Size won’t matter nearly as much at those things. It also helps a lot that these points also help you be more interesting – which is something bigger players fall flat on their faces faking.

4.) Quality Over Quantity.

It doesn’t matter how many weapons or party members you have. If your party does not have the right combination of skills, nor has the right items, you’re never going to slay that dragon. An experienced and well-prepped party of six or seven can unleash a bigger can of whoop-ass far more reliably than a hundred random orcs.

The same goes for any business. It really is all about the quality you bring to the table. Funds and physical resources count for very little if they cannot be used effectively. It’s all about how you use what you’ve got that counts.

3.) Parties With Differently-aligned Members Make for Wider Perspectives. That’s Not Always Worth It.


Bill Sienkiewicz Art For The Dungeons and Dragons Cartoon

Bill Sienkiewicz – Art For The Dungeons and Dragons Cartoon.jpg

While you’ll never get Lawful Good characters to play nice with Chaotic Evil party members for very long, this can often allow for a much more nuanced understanding of how one can approach problems. It’s always interesting to have characters from all parts of the Good-Neutral-Evil spectrum, and it almost invariably makes for a much better story.

While we don’t think you should be hiring evil types left and right, a diversity in views – not to mention in skill sets – can be a major strength for any group. Divergent views however, can also be cause for internal splits.

It’s usually futile to try to build an effective team out of people who dislike each other at a fundamental level. If they won’t be sabotaging each other (intentionally or not), they probably won’t be doing as good a job as they could with people they could actually stand.

2.) We All Love Good Stories.


The Bard's Tale - Interplay

The Bard’s Tale, Interplay. Not Technically DnD but close enough

Interesting quests and characters will always get you much more involved than generic hack n’ slash types of campaigns. While DnD is generally addicting, it’s the campaigns with the best stories that we remember the most fondly and more likely to revisit.

In the same way, a business with a well-presented story or a human face (figuratively as well as literally) is more likely to be remembered. Pair this with an ability to actually deliver and delight  and you’ve got the recipe for customer loyalty – a must for any sustainable venture.

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1.) Always Play Within Your Character’s Traits. -Character sheet

4th Ed. Character Sheet –

Characters that don’t play up to the strengths of their type are rarely effective outside the roles they’re meant to have. Dual class and multi class characters are to be found, sure . And they’re pretty handy for the odd task in the odd place.

But they almost invariably rely on specialist party members to keep them alive until they develop their skills – which is usually pretty late in the game. In a vast majority of cases, two dual class fighter-mages are rarely as effective as one specialist fighter and one specialist wizard.

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Larger ventures will rarely need as many jacks-of-all-trades as small ones. Multi-talented people are great for helping bridge gaps, find ways things could be integrated, and for getting small jobs done in a pinch.

They will however, never be as good at one particular task as someone who’s dedicated their time and effort to it. Jacks of all trades are useful – and often necessary for small start-ups. But specialists will nearly always hand their butts to them at any one task and are more desired in larger businesses.  


Dungeons and Dragons isn’t a game for nerds any more than business is a game for greedy sociopaths. Both business and DnD require diplomacy and teamwork, reward those who plan ahead, and makes it difficult for those who just want to screw around. We couldn’t recommend it more.


Love Dnd? Hate it? Comment below! 


Arthur Piccio manages YouTheEntrepreneur and has managed content for major players in the online printing industry. He was previously BizSugar's contributor of the week. His work has appeared multiple times on The New York Times' You're the Boss Small Business Blog. He enjoys guitar maintenance and reading up on history and psychology in his spare time.