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JULY

24

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Business, Bards, and Bad Rolls: Why TTRPGs Are the Ultimate Crash Course in Chaos

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Business, Bards, and Bad Rolls: Why TTRPGs Are the Ultimate Crash Course in Chaos

Business, Bards, and Bad Rolls: Why TTRPGs Are the Ultimate Crash Course in Chaos
This is how close I was, watching an actual play DND session (Dimension 20) at Climate Pledge Arena in Seattle!

Since no one seems to be interested in the Great Emu War (If you voted for it, read more here!), I’ll be talking about DND.

Screenshot 2025-09-17 at 2.58.45 PM

No, I don’t mean Do Not Disturb... though, honestly, you should put that on while you read this. Trust me, you’re not using it enough.

DUNGEONS AND DRAGONS: the best, nerdiest, weirdest, cringiest, most heartfelt game out there. DND (not to be confused with DAD, though I feel it is something dads might play often!) is something I’m still new to, but I absolutely love diving in.

If you’ve never heard of it, or just picture a bunch of folks in wizard cloaks playing in their mom’s basement... That’s not what the modern DND world looks like! Ever heard of Madison Square Garden? Yeah? A group of seven people playing DND actually sold the place out. In minutes.

Here's the basics. Stop at whichever step gets too elaborate, and you'll still understand what's happening:

  • Anyone can play!
  • It's a storytelling game.
  • The outcomes of your decisions are based on dice rolls.
  • Dice rolls are also combined with character sheets, because everyone is playing a character!
  • You build on the story as a team, though the "moderator" and all the random characters throughout the towns, villages, planets, etc are all played by the DM (Dungeon Master).
  • Sometimes you will play a short story (a one-shot) and sometimes you may play a years long campaign.
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Have you heard of...

  • Vin Diesel
  • Joe Manganiello
  • Stephen Colbert
  • Hank Green
  • Joseph Gordon-Levitt
  • Dwayne "The Rock" Johnson

If you've heard of any of these people, you know someone who has played a TTRPG! (Wait, why didn't you say DND anymore?! The truth is, there are tons of different TableTop RolePlaying Games and DND is one of many. Now that you know it's simply a storytelling game, I will use the proper terminology. Not Kleenex but tissue. And not DND but TTRPG.)

So what does all this have to do with running a business? Or being a coder/developer? Or working in general?

Here’s the thing: TTRPGs make you plan, strategize, and coordinate based on your character’s (or brand’s) strengths and goals. But once the dice hit the table, anything can happen—and you’ve got to roll with it.

Let’s use Toys-R-Us as an example (not sponsored, not affiliated, just vibes).

Quick recap: Toys-R-Us became a thing in 1957 and rocketed to toy-store legend status (at least according to Emily, circa 1998). Then Amazon and Walmart crashed the party, and Toys-R-Us had to file for bankruptcy. They tried to rebrand, then—boom—COVID. Now they’re still around, but in a different form, mostly inside Macy’s.


Now, imagine this as a TTRPG campaign.

My name is Toy. I’m starting my adventure in the big wide world. I pick the USA as my stat block.

DM: Okay, roll for initiative in Toymageddon!

  • Toy: 17
  • Amazon: 5
  • Walmart: 10

DM: Alright, Toy starts with $17M, Amazon with $5M, Walmart with $10M.

Toy: Score! I’m using all my money to expand everywhere. World domination time!

DM: Go for it. Amazon, Walmart, what’s your move?

Amazon: We’ll expand slower—start with books, then games, then toys. Eventually.

Walmart: We already sell toys and people come to us anyway. We’re not stealing all Toy’s thunder, but we’ll keep growing.

DM: Awesome! Now it’s the early 2000s. Everyone seems fine. Fast forward—let’s roll to see how well you handle going online.

  • Toy: 7
  • Amazon: 18
  • Walmart: 16

DM: Bad news for Toy, you owe the banker. And now—COVID! Everyone, roll a death saving throw!

Toy: rolls a nat one

DM: That’s two failures. One more under 10 and you’re out.

Toy: rolls an 11

DM: You’re still alive, but you’ve taken some serious damage. Time to heal.

 
😅 Okay, did I spend too long typing up a pretend script? Yes. Yes, I did.

 

But you get the point: Businesses can plan all they want, but sometimes outside forces just wreck your plans. If your stat block (your business plans, strategies, reach) isn’t up for the challenge, sometimes it’s just down to luck—a dice roll.

Am i saying to never plan for anything at all? Absolutely not. I am saying, what I think is YNAB 's best rule... Roll with the Punches! You're going to face something you aren't prepared for. So be prepared... to be unprepared.

Expect the Unexpected (#BigBrother).

The rules are made up and the points don't matter (#WhoseLineIsItAnyway).

Winter is Coming (#GameOfThrones).

Thanks y'all! It's been real. It's been fun. But let's be real, can we just go play TTRPGs for our job instead? Dropout hire me pls. Thx.

🎲🎲

-Emily

PS: For those in the know... I tend to play rogues. Currently playing as Patchallie Switchfoot, a rogue halfling who has a sarcastic outer-layer and shows her love (And gives bardic inspiration) by insulting her friends. It is nothing like me. At all. I have never spoken an ounce of sarcasm.


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