I've held two sessions so far, and I'm pleased by how things are going. Everyone seems to be having a lot of fun, myself included. I'm still finding my feet though, and stressing about it an unnecessary amount. I've been writing for over twenty years, and I love storytelling. I'm still gaining my confidence for improv, I suppose, and finding my DMing style. What are some things you've all done to keep yourselves from overthinking it? I can't prepare too much without risk of railroading my characters anyway, but the thought of not having enough material makes me unnecessarily panicky xD

 are you making your own campaign or not and do you play in-person or not?

It's a homebrew campaign. We play in person.

do you use IRL maps?

Quote from DOMINATOR2022 >>

do you use IRL maps?

  Yeah, I have a dry erase map and a bunch of dungeoncraft tiles (I'm not an artist) to help me build them and scene set.

1. As soon as a session ends, write down everything that happened in that session, including names and places and NPCs and whatever else you can remember. Being able to reference that sheet rather than trying to remember the name of that NPC from 5 days ago will make your prep work for the next session SO much easier.

2. Incorporate each of your characters' backstories into the game. Not all at once, of course. But at some point during the campaign, each player should have the opportunity to play out some issues from their backstory in their own little character arc. (This also means that each player has to provide you with character backstory!)

3. Don't plan too far ahead. D&D is not a novel that you're writing. It's improv theater. Have some loose ideas of what you want the party to deal with down the road, but leave yourself plenty of options, and don't make any final decisions about what to throw at them until right before you do. Because you never know what the players will do. Let's say you want the BBEG to be a Beholder who lives in a mountain. But then your players go to a port city, steal a ship, and become pirates. Now what? Well, let them be pirates. Have some fun pirate adventures at sea! And then a storm hits them one night and they wake up shipwrecked on an uncharted island. And guess what lives on that island... I'll give you a hint - it rhymes with "shmeholder". 

4. Worldbuilding should be done location-non-specific. What the heck does that mean??? Well, let's say you want your world to have a mountain with caves that lead down to the Underdark, and maybe you think of some cool adventures the party could have in the Underdark. Well, don't put that mountain in a specific spot of a specific mountain range. Just develop the idea on your own, and if the players ever find themselves in any mountain range anywhere in the game world, then just plug that mountain into that spot. 

5. Remember it's just a game. If someone makes a mistake, laugh it off, adjust accordingly, and move on. And try to remember the correct rule for next time. No one can or will ever memorize all the rules to D&D. If something unexpected comes up, rather than stop the game and spend 10 minutes searching through rulebooks and having an argument about how something should work, just make a ruling on the spot. Keep the adventure flowing. Don't let the rules get in the way of a bunch of friends sharing a good story.

6. Snacks. Snacks. Snacks. Heck, fire up the grill once in a while. You can't play D&D on an empty stomach! 

There's nothing wrong with railroading the players. If you're at the theme park do you want the roller coaster to stay on the tracks or jump off for that sandbox freedom feel? Just as all roads led to Rome, all the plot hooks eventually lead to the bad guy you've got prepared. Now the players may go through the desert, mountains, plains or even the sea to end up at Castle Evil. So you set up a variety of beginning quests and then once they pick you narrow it down to that path. You don't even need to prepare too far ahead. If they do something that stumps you or that you weren't prepared for, that's when you throw a random combat encounter at them to run out the session's clock. Then you have until next session to prepare. 

There's also plenty of DM/GM tips videos on Youtube you can watch to see what they do to prepare. 

Whilst railroads are bad, there’s a middle ground between them and sandboxes. It’s not unreasonable to ask the players what they want so you can prepare the next session and/or provide a few specific options for the players to pick from. As the DM they only know so much about your world as you provide them so unless they say something like “we head east” you can detail locations of interest for them to choosing from.

since players will come up with their own ideas to solve situations, one piece of advice I found useful was create interesting problems, not solutions because there’s one of you and multiple players. Then see how they solve it. 

at the end of the day its a game and you need to be having fun, same as the players so if that ever changes you need to speak up. Sometimes this means you set expectations at the start, during a session zero, although I know you’re a few sessions in. 

As Matt Colville once said, as the DM it's not your job to find solutions for your players' problems. Your job is to find problems for your players to solve. 

What are some things you've all done to keep yourselves from overthinking it?

I don't. That is, I don't do anything to keep from overthinking it. Like threads here in the UA and the  Rules & Mechanics forums, I will beat the living hell out of a dead horse until puply, then scoop that pulp up and keep on beating it like I am a tom tom player in a tom tom band.

That said...

I know my world. I create my own worlds, and I know them very well -- better than the players, though I often forget little details that stand out to them. And for those, I have my world bible (setting book). It does not detail everything, because I respond reactively and improvisationally as we go along, but it gives me the stuff that I can draw from to do be able to do stuff with little effort.

I put a ton of work into my settings -- even the simple ones. I just don't worry about the rules for it when I do it, and then I will figure out the rules if I need to do so.

I can't prepare too much without risk of railroading my characters anyway,

"railroading" is little more than taking the Agency of the players way from them explained using the metaphor of they are on a pair of train tracks. The balance here is preparing the background, not the foreground. if the characters interact with a person, you only do them when you need them. If they interact with an idea or a system, that's what you have to have in place ahead of time. And it won't react to them, it will just be what it is.  Old men shake fists at the sky everywhere.

I like stuff like manners and greetings and the folkways of different groups, and those are Ways, and I like stuff like this is what happened in the last 100 years but who the hell knows about the last two weeks. In terms for a lot of the fantasy worlds, when we play this game, we are leaving the outcomes to chance, because the dice are the God of Chance, fate, Destiny, and all that stuff. 

it isn't "how much" you prepare. It is what you prepare. I prepare to let my Players go off and do crazy stuff. I ie that they always think so very differently than I do, so I am interested in what they do when they are in a situation. All I really do is apply the consequences of an action or a decision -- and try to encourage them to pick up a thing or two along the way.

but the thought of not having enough material makes me unnecessarily panicky

Way back when, I used to do a solo dungeon or a dungeon for two using the old rando tables from the DMG in 1st Edition (which was AD&D). You never know what you will be dealing with then, so you have to think up stuff on the fly, and it was a lot of fun. There is very little that comes with less material than that -- but if I know the world, then the rest is easy.

My #1 piece of advice is to watch Matt  Colville’s Running the Game series. It’s a treasure trove of great advice:

https://m.youtube.com/watch?v=e-YZvLUXcR8&list=PLlUk42GiU2guNzWBzxn7hs8MaV7ELLCP_&index=1&t=22s

After that, here are my personal top tips:

1. If everyone at the table is having fun, even if you’re not strictly following the rules, you did it right.
2. It’s okay to make mistakes. Everyone makes mistakes. It turns out that’s the best way to learn how to avoid that mistake again in future. Making mistakes is not a failing, not learning from them is.
3. If something comes up at the table, and you cannot find the rule for it in about a minute, just make a decision, let everyone know that’s what you are doing, and that you will look up an official answer before the next session.
4. Reread chapters 7, 9, and 10 of the PHB, because the vast majority of all the rules that get used just about every session are in those three chapters.
5. Run a Session 0.

Welcome to the other side of the DM’s screen!