A Hole in the Sock

Tomorrow’s the day: Planescape night is coming up (Yay! 💕)!

I’m the DM for this adventure and I can’t wait to drag my players just a little deeper into the sheer madness of the multiverse.

I’ve got something planned. They don’t know anything specific, of course—but they can probably feel it coming, because that’s just how things go in our group. What they don’t know is just how deep in they already are. And I’m not giving away more than that—some of them read this blog, after all. But trust me, you’re so in for it 😈And honestly, it’s such a delight to be able to write that here.

So many stories to be told. (Image by Michal Jarmoluk on Pixabay)

What’s going through my head right now will probably sound familiar to a lot of DMs out there. Tomorrow’s session is basically prepped. I’ve got everything written up in a document on my laptop, and I like to format my notes using lots of different colors—so I can easily tell descriptions from riddles, from planned rolls, from timing for handouts, and so on. Colors are my tool of trade.

My notes are often pretty detailed, because I need that structure ahead of time to spot any potential logic issues or stumbling blocks. But when it comes to the session itself, I barely use those notes anymore. It’s like one of my professors at university used to say: Writing cheat sheets is great—because you put in so much effort that you don’t end up needing them. If I ever hand out a piece of life advice, that might be the one.

But often, my prep looks totally different—because new ideas just pop into my head and get dumped into a second, chaotic document full of scribbles and quick notes. The plan is always to go back later and sort them into the proper structure. That’s the plan, anyway.

Whether it actually happens… well, that’s another story. Once I’ve written something down, the idea starts to grow. That just happens. I think a lot of people know that feeling. And once it starts growing, it gets harder to go back to the beginning and do the organizing and fill in the gaps like I meant to. It’s kind of like eating dessert—once you’re there, you really don’t want to go back to the main course. Most of the time, anyway.

I love Planescape, and I love prepping my sessions. There’s nothing cooler to me than pulling my players deeper and deeper into the setting. But then there are days like today, where my notes are full of holes—like an old sock—and I start second-guessing whether I’ll be able to bring across the next part of the story in a way that’ll be fun for everyone.

I can do it. I know that. I’m good at improvising, I know my plot points, I know where everything’s headed. I know my group, too—I can read the table and pick up the vibe. I know they won’t mind if something doesn’t go perfectly. Still, I find myself chasing this ideal: to walk into a session with much cleaner, deeper notes. Because when I’ve already patched up the gaps in logic and story, I feel more free to be creative in the moment.

My players say they don’t notice any of that. That makes me happy, of course. But the feeling I carry into the evening is a different one.

Will I manage to darn the holes in that sock before tomorrow? We’ll see. I’m motivated, but time is a bit tight (a classic side effect of freelancing). The story’s going to take off—that much I know. And I’ll allow myself to spoil just this much: some of the decisions made so far might feel very different in hindsight.

Let’s face the Dark, Cutters!

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