I don't care how much you plan ahead. You will end up winging it at some point. At many points.
Back in the Bad Old Days, modules had to be hand-keyed. Old school D&D
modules consisted of a simple, gridded map and an incomplete key, which had to be filled out by the DM. You had to add monsters and treasure to your rooms.
Because I was so strapped for time the first time I ran for the kids, I actually ran off an old key I wrote back when I was something like 15 years old, and half the stuff in there I only remembered it when I was actually running the module. Which meant that one of those monster encounters consisted of a forgotten human berserker lurking inexplicably in one of the rooms.
I mean...it's a different time, right? They're not gonna just murder-hobo the guy. So they struck up a conversation with him, which meant I had to come up on the fly with a reason a lone human man might be hanging out in a monster-filled labyrinth.
So the story I came up with in that moment was that he was Rolf Larsson, a former soldier from Riverport who had had to go into hiding because he had been framed as the mastermind behind a coup attempt within the Duke's militia and they were looking to hang him on trumped up charges.
Why I went there, I have no idea. I opened my mouth and that came out.
My daughter and husband have always loved mysteries and intrigue, and all three of them enjoy role playing and figuring things out. So they insisted on pursuing that story line.
I had to stop and level with them. I said, "I don't have a story for that fleshed out. But if you give me till next time we play, I will have you a mystery to solve surrounding this plot line.
So that session, they went ahead and explored the rest of the module and by the
next session, they rooted out an elaborate plot by a bad faction of the militia, rescued the Duke, gained intel from the Bad Guys, and joined forces with the Captain Mercutio of the Riverport militia to splinter and defeat the threat to the town.
By now, the Rebels had made a bit of a name for themselves in the city, and had
gained the trust and regard of the Duke himself (and maybe more importantly, the Duke's steward, Regus), so they hired the Rebels as a special unit the Duke relied on to take care of special cases. He put them up in some apartments on his estate and that'show the Riverport Rebels became Duke Orsino's special task force.
So to translate, the newspaper says "The Duke was going out of town with three guards, and two random people jumped out of the bushes wearing armor and deadly weapons. When this happened, two of the three guards attacked Captain Mercutio, but luckily three people (Sir Peter, Stephanie, and Taijitsu) fought the ambushers and defeated them. Captain Mercutio was hurt, but survived. The Duke rewarded Sir Peter, Stephanie, and Taijitsu with Rolf's freedom."
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