There may also be a playstyle element to this problem as well. Some DMs and players like a more scripted linear adventure, with a plot, and defined obstacles. Others may be more comfortable with a more “sandbox” sort of playstyle, in which there is much more freedom to act.

In my early D&D days, our group had two main DMs, me and George. George is, among other things, a movie scriptwriter. His adventures are always interesting, detailed, intricate, and closely plotted. The party pretty much has to follow the course if the whole thing is to work, and if they stray too far off, events are likely to happen to shunt them back on course. It was very hard for me to adapt to. But I eventually relaxed my playstyle, and resolved to just enjoy his stories, and had great fun. Conversely, my world is a big sandbox. I decide where everything is, and the characters decide how to respond to everything. “Here’s what you see. What do you do?” George felt lost in my world; there were no clear channels to take to further the adventure. He eventually adapted to my style as well, and became a very creative player.

So, you and your players may just need to come to some accord as to what game you are playing, how much the plots matter, and how much improvising is wanted.

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I’m a “big sandbox” kind of guy. I try, in my campaigns, to develop several events going on, and let the characters discover various bits about them, depending on where they go and what they do, and they get to decide how (or if) to interact. Right now, I’ve got two parties of adventurers roaming my world, on a continent about the size of Australia.

Among other things, they’ve found a necromancer who wants to become Santa Claus (both parties have decided he’s more-or-less harmless for now; one party has hired some of his rent-an-undead teams). There’s a mad demon-worshipping wizard, who has befriended both parties to play with; he helps them out often, but also summons demons to fight them just for the fun of it.

One party is looking at a blue dragon who has enslaved a bunch of gold dragonborn related to one of the characters. The other party has been hired by a Revenant to help him get revenge on the evildoers who slaughtered his family and took their ancestral castle.

Both parties are connected in different ways to a plotline involving a Hobgoblin Warlord, who is amassing an army of thousands in order to fight a Kraken underwater and drive it off of a shipwreck that has the Holy Grail in it. One party has fought with the Warlord, been captured and sent to the slave mines, and escaped the mines along with a bunch of rescued slaves. The other party has decided to enter a pact with the Warlord in exchange for being among those who benefit from the Holy Grail, and will be helping by casting Water Breathing on the thousands of goblinoids so they can dive in and fight the Kraken.

There’s also the first clues now occurring to both parties involving a plot by the Mind Flayers to break the 7 seals and bring back Cthulhu and the other ancient gods. One PC party includes a Triton, whose tribe guards one of those seals. The other party includes a mad Warlock, with an Old One pact, who has been to the Mountains of Madness, and probably will want the Mind Flayers to succeed.

I outline these storylines, determine and place the major players, and the timelines their actions occur in, but don’t spend a lot of time detailing the specific adventures unless and until the adventurers decide to look into a particular course of events. I only try to plan a couple of play sessions ahead of the events currently occurring in the play sessions, which also gives me good flexibility to determine how the BBEG(s) react to what the PCs do to their plans.

And sometimes it just doesn’t go according to any of the ideas I had. In an older campaign, the party decided early on to literally ignore all of the encounters, adventures, cities and known territory, everything that I had prepared, and just go exploring in the wilderness instead. They noticed a road on the map that went off into the desert, and decided to chuck the whole idea of civilization and the known world, and go exploring overland. They did that for literally years of play, and that party never even entered the whole settled/civilized/mapped/politically subdivided half of the continent.

I like that style of play. But some people it would drive nuts.