Using AI to play Role Playing Games – Building tools to play Dungeons and Dragons is playing D&D…?

I wanted to see how much time I spend playing D&D with AI and working on the tooling for playing D&D with AI. Here it is, looking at everything back to my first session with ChatGPT in 2023.

I’m suspicious of the “prep and worldbuilding” quantity. Sort of. First, that is part of playing and having fun, so it’s not distressing. It’s making up the world, discussing things like how many farms you need to support a village of 200 people – you know, really Dungeons & Dragons stuff! But, it’s the harness building that’s more interesting, and likely more accurate.

The reason there is not much “harness” work in 2023 is because there was no harness work to do. The only “harness” was copy-and-paste, plus typing. As GPTs, projects, MCP Servers, and now skills were added…and then Claude Code…there was more potential, and you can see that I enjoyed building tools to play, sometimes more than playing itself. This is the cobbler’s curse: you love building shoes so much that you often don’t have time to wear them and walk around.

The cobbler’s curse

I don’t think this is a failure mode, exactly. Building is a hobby too, or at least half of it. Nobody makes me do any of this. If I enjoyed the shoes more than the shoemaking I would have stopped at the copy-and-paste stage in 2023, which worked fine, and I would have played a lot more D&D and learned nothing.

But there is a version of this that is a warning, and it is not about D&D. Swap “campaign” for “platform” and the chart is one I have seen in a hundred enterprises: a team that started out delivering something, discovers that the tooling is more tractable than the delivery, and ends up with a beautiful internal developer platform and not much shipped on top of it. The tools are legible. The work is messy. Guess which one is more fun on a Tuesday afternoon and looks better on your resume.

The difference is that when it is your hobby, nobody is waiting on the shoes, and just working on them is fulfilling and has, you know, life ROI.

The last quarter is down to 38%, for what it is worth. Maybe I have finished. That would be nice, because the setup I have now is genuinely good and the whole point of it was to play. I just need to go and use it more.

Also, through-out the rest of the year I’ll be talking about playing D&D with AI at several conferences. Check out where I’ll be speaking, and come check out how things progress over the next few months.