D&D: Storytelling about Leveling Up
Apr. 27th, 2026 11:24 amI mentioned yesterday that it was time to level up in my D&D game. Indeed, the players spent hours of table time updating their character sheets. That's a kind of bookkeeping time sink I've been trying to avoid in this game.
It could have been worse, though. We could have made it worse. We could have tried roleplaying— and roll playing— through the minutiae of everyone finding tutors (they're in a new city), arranging relationships, and figuring out what happens over the course of a few weeks. I've been in games that are like that.
I've also played in games that are the complete opposite of that. I remember one GM just told us after an adventure, "Great! You all gain a level. Update your character sheets." Many of us players, accustomed to all the accounting of crunchy games like D&D were all 😳. I mean, the GM didn't even tell us how many experience points we'd earned! 🤣
Inspired by that GM, I proposed to the players we could skip all the fuss of how leveling up happens in-game, make changes to stats quickly, and get on to the next adventure. To my slight surprise, the players wanted to spend at least some time on it, to see what leveling up in my game is like. Plus, they were curious to see if playing through getting trained could, say, help them develop their characters by finding new allies. Fair enough!
Still I didn't want leveling up to become a full game session— or longer. To help focus our efforts on the high points of storytelling rather than getting lost in the minutiae of "I rolled a 7 on my check! What happens next?" I proposed a narrative framework that's like a writing prompt: Think of 1 bad thing (challenge, adversity, setback) that happens and 2 good things.
The players all embraced this prompt. Some did a lot better than others with it, though. I mean, that's to be expected. Some players are more creative roleplayers than others and/or are more familiar with the game. In my house it's not about grading everyone, it's about working with what we've got and making it fun.
Keep reading: Two examples of "training montages" we created in my next blog.
It could have been worse, though. We could have made it worse. We could have tried roleplaying— and roll playing— through the minutiae of everyone finding tutors (they're in a new city), arranging relationships, and figuring out what happens over the course of a few weeks. I've been in games that are like that.
I've also played in games that are the complete opposite of that. I remember one GM just told us after an adventure, "Great! You all gain a level. Update your character sheets." Many of us players, accustomed to all the accounting of crunchy games like D&D were all 😳. I mean, the GM didn't even tell us how many experience points we'd earned! 🤣
Inspired by that GM, I proposed to the players we could skip all the fuss of how leveling up happens in-game, make changes to stats quickly, and get on to the next adventure. To my slight surprise, the players wanted to spend at least some time on it, to see what leveling up in my game is like. Plus, they were curious to see if playing through getting trained could, say, help them develop their characters by finding new allies. Fair enough!
Still I didn't want leveling up to become a full game session— or longer. To help focus our efforts on the high points of storytelling rather than getting lost in the minutiae of "I rolled a 7 on my check! What happens next?" I proposed a narrative framework that's like a writing prompt: Think of 1 bad thing (challenge, adversity, setback) that happens and 2 good things.
The players all embraced this prompt. Some did a lot better than others with it, though. I mean, that's to be expected. Some players are more creative roleplayers than others and/or are more familiar with the game. In my house it's not about grading everyone, it's about working with what we've got and making it fun.
Keep reading: Two examples of "training montages" we created in my next blog.