A lot of the time when I’m working on something for an adventure I find myself asking: ” is this is stupid?” Or maybe I’ll be thinking that whatever I’m working on, for whatever reason, just isn’t “good enough.” I’ve thought these things about encounters or even entire game sessions or story-arcs that I’ve ran, only to be approached by players afterward telling me how awesome the encounter or session or story-arc was. Meanwhile, I’m thinking “Really? Are you sure you don’t mean that everything felt ham-fisted, clunky, and obvious? Because I felt like that more than once…”
The thing is, if you’ve done your job well then you’re players never noticed those moments where you flipped through your notebook, scanning blank page after blank page, before you pulled something out of your ass. Likewise, they probably didn’t feel like the twists and turns that you plotted and schemed over were as obvious as you thought they were. Of course the magician isn’t surprised when he pulls the rabbit out of his hat because he crammed the damn thing in there to start with. Just like the magician isn’t impressed by his own tricks, there are times that we as dungeon masters are also not impressed with our own tricks. But whether you’re a magician or a dungeon master the only thing that matters is how impressed your audience is. If they look like they are having a good time and tell you that they are having a good time then guess what? They probably are. Even if you feel like what you are doing is obvious or amateurish.
Chances are that you have way higher expectations for yourself and your adventure than your players do. This is a good thing, but don’t hold yourself to such unreasonably high expectations that you don’t even get started planning your adventure because your idea isn’t “perfect.” And don’t let self-doubt cause you to falter halfway through your campaign or story-arc.
You don’t have to be a Pulitzer Prize winning author to tell a good story, and you don’t have to be Gary Gygax to design a good dungeon. Hell, take a look at some of the silly shit in old modules. There are a lot of things in those old adventures that, when looked at objectively, just look completely stupid. And a lot of it is completely stupid, but that doesn’t matter because it’s also FUN. If the story you’re telling has plenty of opportunities for players to make meaningful decisions and a few hooks that snag on the personalities of the characters then it’s probably an excellent story. If your dungeon encounters have a good balance of risk versus reward and give different classes or types of characters the opportunity to shine at different times then they are probably excellent encounters.
Save fretting over every last detail and worrying about whether things are perfect or not for the novelists and go write your adventure, no matter how stupid you think it is.