Prologue: Why the heck did I sign up for yet another project?
Welcome to my series of articles examining tools for GMing, particularly focusing on organizing and tracking your overall campaign and associated notes. I am certainly not the first person to discuss such things on the internet, and I haven't quite finished Elden Ring yet, so why am I spending time on this? Short answer: one of the regular members of my gaming group (he knows who he is) started a campaign of Masks: The New Generation recently and in our group chat asked how I organize my notes for the games I have run. He had no way to know this intersected with my having read A System For Writing1 and various Personal Knowledge Management System (PKMS) materials over the past few years. Having inadvertently triggered the "your ideas don't do any good if they just live in your head, you have to publish them in some form!" trap, I threatened to write an essay I can actually put out in the world instead of having it disappear into the ether of chat, and here is where we find ourselves.
My overall goal is to share what has worked well (and not so well) for me. This is by no means the one true way to do things, and there are innumerable options out there that I haven't even had the time to try.
Who Am I?
I've been involved with RPGs for some ~30 years, since I got the good old Red Box D&D as a Christmas present in I think 8th grade.

Coincidentally, as I write this earlier today, my dad was telling the story of getting me that boxed set and thinking "oh man, nobody is going to want to play this with him". I ran that intro adventure for him and my sister, then my buddy Zach, then Tanguy, and within about a week pretty much all my friends had joined the campaign and D&D became our main social activity for most of high school. I still regularly see (& play!) with most of those guys. Turns out it was a pretty good present after all. Thanks Dad.
I've mostly been the GM for various groups, and while I've certainly run plenty of D&D we tend to play other stuff more often these days. I enjoy trying out different games and seeing what makes them work or not, so we'll play everything from high drama PbTA to hyper-tactical Lancer to OSR open table West Marches inspired setups. Given we're all busy adults, we're finding most success these days with roughly 8-12 session shortish campaigns, sometimes leaving openings to come back for sequels or additional "seasons". While I GM most of the time, folks take on one shots or short games on occasion, and as mentioned earlier someone else has recently started running a campaign giving me the chance to actually play for more than a session or two.
I vastly prefer playing in person, and Tuesday nights have been game night at our house for years (starting at 8pm sharp 😴). We shifted online for a while in the middle of Covid, but got back in person as soon as we could all get vaccinated and folks felt comfortable. I do maintain a ~monthly online game with some of the folks who played in that first Red Box campaign and now live scattered across the country, where after having GM'd for a couple of years we're just starting a new campaign with someone else running things.
The Overall Plan
I plan to start off as practical as possible discussing the actual tools I've used recently. First will be Obsidian.md (my current setup of choice) followed by using Google Docs or similar online office suites.
After that I plan a rundown of several campaigns of different lengths and styles that I've run over the past couple of years, for each one talking about the combination of the game and the tools I used for it.
There may be a few diversions along the way, but I eventually plan to take a stab at examining some of these tools from the perspective of a player instead of a GM. (Don't tell anyone - this is at the end because I mostly GM. I need to buy some time as a PC in our current game, so I can have a useful opinion.)
Announcing Future Badness
One idea that has come up repeatedly and really resonates for me - Organizing is not Doing. I definitely have a weakness for the Shiny New program or methodology that will solve all my problems if I just invest the next N months in switching over to it. This is a trap. I know this is a trap, and I still fall for it. But it is my duty to iterate - I hope there is something useful for you if you are a GM or player of roleplaying games (or just stumbled across this somehow). But please, don't spend so much time trying to craft a perfect organizational system that you don't actually do the core of our hobby. Play games. Run games. Prep for your games, but make sure you are doing real & useful prep work, not testing plugin after plugin after plugin in the hope that somehow the resources you need will magically appear.
Kevin Crawford touches on a similar idea in Worlds Without Number: "It's all too easy to exhaust both your time and your creative energy on peripheral matters, leaving you stressed and unequipped for for the next session of gaming."2 He was talking in the context of spending your time preparing irrelevant detail that doesn't matter, but I find the same is true for me in regards to endlessly tweaking process and tools instead of just Doing the Work. When I actually focus on doing the prep work, I am much more likely to end up in a flow state and feel good about having accomplished something at the end instead of getting more and more stressed out.
Conclusion
Whatever your relationship to the hobby of tabletop role playing games, I hope you find something useful in all this. If you have any questions, feedback, suggestions, or general comments, please feel free to send them my way at [email protected].
Next Up: Why Obsidian?