Hiya 👋
I’m 3 days away from tying the knot with this cutie.
This week, you get to hear from my brother and best man, Jake.
Jake is a software engineer for Wirecutter and the coolest nerd I know. He can solve a Rubik’s cube with his tatted arms.
While you were burning sourdough bread during the pandemic, Jake was leading a Dungeons and Dragons campaign.
Whether it’s bread or bards, you can learn a lot from any hobby if you stick with it. Here’s what Jake learned from leading D&D for three years.
In January 2020, I convinced a few of my closest friends to try out Dungeons and Dragons. Last week, we finished our campaign.
After 83 sessions, spread over three years, we finally killed Strahd von Zarovich, the Vampire Lord of Barovia.
I learned a lot. Mostly about how to be a dungeon master and how to navigate scheduling conflicts between seven adults.
But I learned a bit about life as well.
Don’t let the dice tell the story
Dungeons and Dragons is a weird game. You might imagine nerds hunched over a table, stuffing their faces with Doritos, and praying that the dice roll their way.
And you’d be right.
Swap out charcuterie for Doritos, and that’s what my house looked like most Tuesday nights for the last few years.
But how does it actually work?
In its simplest form, D&D is collaborative storytelling. The dungeon master presents a problem. The players present a solution. The dungeon master determines how likely they are to succeed. And the dice decide if they fail.
Do that for about 250 hours, and you get to kill the Demogorgon (fun fact: the Demogorgon in D&D is actually a demon lord with two baboon heads and tentacles for arms… and still no match for Eleven).
As the dungeon master, I really, really want my players to succeed. I want them to survive and kill the Big Bad Guy and save the world.
But the dice exist for a reason.
If everything is perfectly predictable, then the story would suck. Looking at you, Hallmark.
In our final fight against the evil Vampire Lord, Strahd von Zarovich, everyone was dead or dying except for our barbarian, Lubash. I thought this three-year-long campaign was about to end in the worst way possible — the bad guy was about to win. The world was about to not be saved.
Both Strahd von Zarovich and Lubash are on the edge of death. It’s Strahd’s turn. He knows that he has won, and he does what villains do — he gloats.
“Love is when we choose where our spirit will break,” he says as he plunges his blade into the unconscious body of Lubash’s brother.
Now it’s Lubash’s turn.
I know how much damage it will take to kill Strahd. I know how much damage Lubash can do with one attack. I know that he has to hit Strahd two times to kill him.
His first attack… misses.
There is only one way that Lubash can kill Strahd now. He has to roll a perfect 20. There is a 95% chance that this campaign is about to end in complete failure.
But the dice exist for a reason.
He rolls a 20.
He does just enough damage to kill Strahd and save the world.
I couldn’t have written a better ending.
While this was unfolding, I wanted to step in. I wanted to rewrite some things. I wanted to go full-on deus ex machina - “Actually, the goddess of death really wants Strahd dead, so you come back to life with one hit point.”
I’m the dungeon master. I could have interceded.
But my players, and the dice, had a story to tell. If I didn’t let it play out, I would have squashed this incredible moment.
Life has the weirdest way of happening.
We have these ideas and plans and paths mapped out.
So many things that are completely out of our control impact our lives in significant and insignificant ways and there is absolutely nothing that we can do about it.
We didn’t pick where we were born. We didn’t pick when we were born. We didn’t pick whether or not we like cilantro.
We don’t control the weather or housing prices or when George RR Martin will finish “The Game of Thrones”.
So much of life feels completely random and outside of our control. And that’s ok. That’s what makes it interesting. If life was perfectly predictable, it would be boring.
Life presents problems, we present solutions, and then we roll the dice again.
The dice exist for a reason.
But it’s still your story to tell.
Let your friends surprise you
As the dungeon master, I have a story in my mind. I want the players to kill the evil Vampire Lord. But I want them to decide how they do it. How do they navigate the world that I have created? How do they level up and evolve as characters?
I often want to make these choices for them. I know that they need access to sunlight to kill Strahd von Zarovich, so I want them to select the spell Sunbeam. I know that they will need it. They don’t know that. I could tell them to pick Sunbeam, or steer them towards picking Sunbeam, or force them to pick Sunbeam.
But that removes the players’ agency. This tendency to steer players in a particular direction is so common that it actually has a name — “railroading.”
As a dungeon master, it is my job to present a problem to the players; it is their job to provide the solution. If I don’t give them room to make choices, then I am no longer playing Dungeons and Dragons; I’m writing a book.
I used to prepare for hours before every session. I would write monologues and beautiful scenes and eloquent backstories. But I would only use about half of this work.
Why? Because my players never made the choices that I would make.
Their current quest is to safely deliver the mayor’s daughter to the town of Vallaki. The roads are dangerous. Every night is a risk to their lives. The mayor does not trust anyone but them to transport his daughter across this perilous valley. So the players are going to go directly to Vallaki, right?
Wrong. They thought the mayor’s daughter was sad, so they took a detour to swim in the lake.
I didn’t have anything planned for this lake. I forgot this lake existed. It was just a bit of background for the real story - the story that I wanted to tell!
But my players choosing to go for a swim is the real story. Were they attacked on the road? Yes. So many times. Did the mayor’s daughter die? Almost. So many times.
But it forced me to be flexible. I improvised an underwater puzzle that was later used as a huge plot twist. If they had gone directly to Vallaki, then I couldn’t have set up such an epic moment later in the story.
That’s why, I now prepare for about 30 minutes before a session. I write the first scene. I write down the information that I want to convey during this session. And then I let them surprise me.
I am trying to approach my friendships with similar grace and flexibility. I can be so judgmental and harsh. I make decisions on my friends’ behalf all the time.
“They wouldn’t want to go. So I’m not going to invite them.”
“They haven’t called to check on me in months. So they wouldn’t want to hear from me.”
“They don’t like to read. So I’m not going to bring up this book I’m enjoying.”
But people are not static things. They change, and develop, and mature. And if we don’t give our loved ones the space to grow, then who will?
✌️
— Jake