While I'd played tabletop role-playing games before The Sheep of Sherringale was the first game I ever ran as a game/dungeon master. It's oddly nervewracking, something like a job interview, where you hope you've prepared for their questions, but can never really be certain.
The Sheep of Sherringale is a short adventure I put together inspired by A Wild Sheep Chase, but this time designed to be the introduction of my four person group to the world of D&D; the first many of them had experienced of it. It involved the characters of the party finding themselves wandering into a small, but bustling, market town within which they happen upon a very strange sheep. It leads them on and adventure that sees them discover an unfortunate wizard, some lucky, but deeply unpleasant goblins, and an unexpectedly powerful wand. Re-reading it recently, I can see how much I'd overthought it, trying to predict everything that they might try and noting at least some means of dealing with it. It's a fool's errand really, I've learned they'll always unexpectedly find the gap in your planning and drive straight through it regardless of the number of notes you've made in adavance.
I shouldn't have worried; everybody had fun.
And that's really the wonderful thing about it, during lockdown we managed to play a series of adventures armed with not much more than some character sheets and a zoom meeting. I got a subscription to the fantastic D&D Beyond which allows us to manage all of the party's characters and rolls online and allows me to share any homebrew elements I've manifested for the story. Since that first game, the party has found themselves causing chaos, releasing demons, rekindling ancient conflicts, taking command of a ship of undead pirates and making perhaps one friend.
I've now written a clutch of adventures that we've either run or are yet to play, and while the nerves haven't really dissipated they're now more attuned to worrying that the party won't enjoy the game, rather than the wealth of unknowns I'll face from them. There really isn't anything quite like tabletop role-playing, I'm certainly not the most gifted or entertaining game master that's ever existed, but the fact that even I am able to run something that has managed to churn out hours of fun is entirely on the shoulders of the game itself.
The design of D&D 5e (The fifth edition and the version we're playing) gives enough wiggle room that I don't have to be an expert on every rule, or constantly consult tomes (though I still do from time to time) it gives me the opportunity to go with my gut, or give the party the benefit of the doubt, with a minimum of fuss. That really keeps things moving along and it allows the group to throw out ideas without having to reason through the game mechanics to do so. Sure there are pages in rulebooks written about how to brew potions and poisons, but if the party wants to apply a mild poison to arrows by dipping them in cat poo, I'm not going to disallow it, just perhaps roll a constitution check to see if you can do it without barfing.
Honestly, it's some of the best time I've spent in recent years, especially in the midst of the pandemic.
If you're unfamiliar with Dungeons & Dragons, or how a game of it is run I recommend Matt Colville's Youtube Channel for further enlightenment.