Following on from the question How can I make sure my players' decisions have consequences?:

I'm frustrated as a DM because I feel like the different players / PCs in my group want different things, and perhaps this group is doomed to fail.

The wizard / the wizard's player (sometimes I struggle to tell the difference) is pretty cautious, in the sense that he wants to blast everything with his highest level spells, regardless of opponent strength, and then immediately take a long rest.

The druid's player likes doing things that would be in character even if they aren't completely optimal (not totally stupid though), and she also likes the feeling of danger - she's told me before that she gets a bit bored of encounters that are too easy, and the solutions I can think of to that are either to make sure there are multiple encounters in a day, or to make the individual monsters harder, but then that exacerbates the wizard's desire to take a long rest after every battle.

We also have a monk, whose (brand new to DnD) player has told me that he is frustrated by doing less damage than the other PCs (particularly the wizard) - and I don't think he really understands how much it hurts him to have adventuring days made up of one battle and then a long rest, because the wizard is throwing two fireballs per battle, and the monk isn't getting any short rests to get ki points back, or any battles where he still has resources and the wizard doesn't. (We also have a rogue, but she doesn't get anything special from short or long rests and seems happy to do whatever anyone else wants).

So days with multiple encounters and short rests are preferable to me, the druid, and the monk, and is also the way the game is ''supposed'' to be, if that means anything. One battle then a long rest is preferable to the wizard (for obvious reasons, I guess), and the rogue doesn't mind. I'm frustrated that in a recent session, what was supposed to be multiple encounters with short rests (and cool treasure!) turned into one minor battle and a long rest. Is this a sign that the players are too different for us to happily play together, or just that I'm a bad DM?

How do I run sessions for this group of players when they have such different preferences? Is it possible?

Although @aslum's and @J. A. Streich's answers talk about not being able to take Long Rests as frequently as the Wizard would like, no-one has mentioned that this is explicitly stated in the PHB page 186 under the definition of a long rest:

A character can’t benefit from more than one long rest
in a 24-hour period, and a character must have at least
1 hit point at the start of the rest to gain its benefits.

So the party are not just waiting another 8 hours per Long Rest. They are waiting 24 hours.

There's a few things you can do to help solve this.

Not everywhere is safe to take a long rest

If you try to take a long rest somewhere unsafe there's a good chance your rest will get interrupted, and then you'll have to start again. Dropping a DM hint (such as "from the tracks through here it's obvious this area sees a lot of traffic") that an area might not be safe, especially early on, can help encourage the party progress further.

A long rest is 8 hours

Trying to sleep and rest when you're not tired is kind of hard. Worse, people have natural rhythms to their sleep cycles, and trying to change it is hard. If they take an 8 hour rest in the middle of the afternoon, they're still going to be getting sleepy in the evening, and if they do keep on with their aberrant rest/wake cycle you might want to apply some variant of the fatigue rules.

Some monsters are more effective during the night / NPCs might be sleeping

Finally, if they're taking rests at weird times, they're going to end up running into monsters during the night, and some monsters could have an advantage whether from being nocturnal or the party not having Darkvision. It might also make meeting friendly NPCs harder!

You seem to be running a very sandboxy adventure.

In your other question you've written:

They were here because they were heading for the town beyond, but they had no known time pressure to get there, and they specifically knew that on the way they would pass a dungeon full of monsters that had been terrorising the region.

and:

So I guess the best thing, as several of you have suggested, is that rather than try to force the PCs to do anything, I just focus on what the monsters will be doing - the situation in the region will clearly get worse because they didn't deal with the dungeon yet.

You told your group: "there are some monsters over there" and you expected them to decide to walk over and fight them. Now you're planning the consequences the group will face because they didn't walk over and fight them.

That's a valid approach, but it's very different from the one I use (and that other DMs use). That approach is to give them plot hooks.

• The villagers from the last town should have explicitly tried to hire the group to go clear out this dungeon.


• The characters should have heard rumors of valuable treasure hidden in this dungeon.


• The characters have backstories, yes? Maybe one of the characters has a backstory involving a side villain and the side villain is somehow connected to this dungeon. Maybe there's some other way you can tie the backstory into this.

In my most recent adventure, I took it a step further. Every time the group talked to any NPC, I invented some sort of quest or task that the NPC wanted the group to do. Some of the quests were evil; some were good; some were lucrative. Some were obviously stupid. There were three witches, each of whom wanted the group to kill the other two. It quickly became apparent to the group that they were going to have to decide which quests to follow. But I made very sure that the group did not lack for quests. It worked really well!

A side effect of offering these quests is that you can give them quests with time pressure, which will solve your long-rest problem.

The Party

You have a balanced party. What they want makes sense.

• The wizard is pretty cautious... because they are wizard and are squishy.


• The druid's player likes doing things that would be in character even if they aren't completely optimal, and likes the feeling of danger... Because they are cool Druid, and there is depth there. Right.


• We also have a monk, is frustrated by doing less damage than the other PCs (particularly the wizard). Yep. But monk's get really neat abilities later in the game, and it makes sense that player would feel a little underwhelming at the beginning.

Long Rests

So days with multiple encounters and short rests are preferable to me, the druid, and the monk, and is also the way the game is ''supposed'' to be, if that means anything. One battle then a long rest is preferable to the wizard (for obvious reasons, I guess), and the rogue doesn't mind.

Great. Actions have consequences. Party wakes up 7 AM. Eats breakfast. Runs into some Orcs. Fights 3 rounds of combat (3 rounds * 6 seconds is 18 seconds later) and then wants to go back to sleep at 8 AM. So, you're the DM, what do you do?

Actions have consequences. Options you can use:

• 
  Monsters have friends. Ambush them two hours later, ruining the long rest, when the an orc search party looking for the missing patrol the party just killed. Don't always interrupt sleep, but at sleeping near the enemy at 10 AM is bad idea in real life. A Nightmare Hag would love feasting on a party that only stays awake for an hour at a time.


• 
  People have circadian rhythms. You can't fall asleep, the bright sun in your eyes and heavy breakfast YOU JUST ATE are preventing you from getting any shut eye. After laying there restless for an hour or so, what would you like to do? (and the rules support this (thanks Black Spike for finding PHB page 186) :
  
  

  
  

  A character can’t benefit from more than one long rest in a 24-hour period, and a character must have at least 1 hit point at the start of the rest to gain its benefits.

  
  

  
  


• 
  Things don't stop because the players sleep. While the party is asleep, the BBEG conquerors more land, takes more prisoners, and magical darkness spreads to the edges of another town. The big bad kidnaps one adventurer's relative, and kills 5 town guards. It might have been prevented, but you were asleep. The king is angry, he hoped people with your skill wouldn't be caught laying down on the job.


• 
  Things happen at specific times "You can sleep, but you have to meet with Balalabad in an hour, and you are an hour and a half travel time from them at normal walking speed. Guess you don't want the reward for the gem you risked your life to steal from the giant for them."


• 
  Let them split the party You have two players who want sleep, two who want to keep going. The monk and druid decide (maybe with the helpful DM comment, "just because they are sleeping doesn't mean you have to.") to keep going while the wizard and rogue snore. I don't often suggest splitting the party, but I don't think it would split the party. I think the rogue will likely decide the rest isn't worth not getting the XP and the possibility the monk and druid might not share their findings. Now, will the squishy wizard still think sleeping alone in the middle of dungeon full of hostile monsters is the best course of actions?

I'm frustrated that in a recent session, what was supposed to be
multiple encounters [became] one minor battle and a long rest.

Why won't the encounters just happen next session What held off the other encounters? Why did one encounter and sleep take a whole session? I means sleep, when you let them actually sleep is, "Oh, you want to sleep? Alright... You go to sleep." (give time for someone to say if/who is on watch. If no one, then you'll have real fun.) "You are woken up an hour later to the strong hands (or tentacles) wrapping around your arms..."

Sooth Your Doubts

Is this a sign that the players are too different for us to happily play together, or just that I'm a bad DM?

Neither. Long rests are often points of contention between players and DMs, until or unless expectations are set. I think it is a common struggle with caution and risk. Some of it can be mitigated in game as above. Seeing that things happen in the world while the party argues or sleeps make the game world feel more real. That characters exist in a larger world, not that the world exists for the players to live in. It isn't a video game with a pause button.

Some of it might have to come from a session 0 like talk, where you ask them what their expectations are, tell them what yours are. In it assure your wizard player that, "I'm not here to kill your character. I'm here to make your character shine by giving them opportunities to pull through when the chips are down. To do that, there will be some risk of character death, but without the risk the reward isn't as meaningful. No one likes the store about the wizard who went to sleep. They like the story about the wizard who used his last spell slot to cast enlarge on the party's monk (who only had one hit point left) and the monk super puched a dragon in the face as the final blow in an epic battle. Trust me not to be gunning your characters down, and take a little more risk -- it will be worth it."

To summarize the problem:

• Player One wants an infinite sequence of pitched maximal-force battles followed by long rests


• Player Two probably wants, but cannot articulate, a sequence of days with more battles punctuated by short rests, and comparatively fewer long rests


• Player Three has no expressed mechanical preference, but in a desire for "more danger" probably leans toward Player Two

What you can't do:

Assuming that assessment on your part is correct, Players One and Two are in direct opposition and their desires cannot be mutually satisfied at the same time. You cannot both have and not-have all of those long rests.

What you can do:

1. But you can satisfy these desires sequentially, one at a time. If my assessment is correct and players two and three are in agreement, you can write adventure arcs catering to them roughly 2/3 of the time, and to player one roughly 1/3 of the time.




2. Alternately, as a frame challenge, you can decide which one (or more) of them are "correct" and cater only (or mostly) to them. I am going to go out on a limb and suggest that in this case, Player One is, intentionally or not, deviating from the spirit of the rules, trying to avoid the issue of strategically managing spells over the course of a day. He effectively wants to buff himself to constantly maximum strength with all those long rests, and probably should not be indulged very often.

How To Do It:

Either of those solutions, though, involves shutting down Player One's long rest strategy some or all of the time.

1. You can do this on a meta-level, out of character, either by explaining to that player that he's having harmful effects on the other players. You can, frankly, just disallow it. You're the GM and other players get votes about party activities. I find that unsatisfying, though.



2. 
   

   Time Pressure! There are infinite opportunities to create time pressure in a game that simply preclude Player One from spending each adventuring day as 15 minutes of furious action, followed by 23 hours and 45 minutes of rest and I've probably used them all:

   
   
   
   
   

   • The Deadline: "If we don't make it to the top of the Ziggur-mid of Doom by Grunsday the 27th to shut down their foul ritual, they will succeed in summoning Zuul!"

   
   

   • The Chase I: Whether they're chasing someone over the course of a single day, or an extended period of weeks, nothing adds time pressure like a chase.

   
   

   • The Chase II: As above, but now the party is being chased (probably by a force, not an individual) and need to make it to safety.

   
   

   • The Race: An unspecified deadline, where all the group knows is that some other active force is pursuing the same goal and they need to get there first.

   
   
   
   

I find time pressure (and related strategies, like environments that are hostile to long rests) more satisfying and effective because rather than just dictating something out of game, or using indirect hints like wandering monsters, the time pressure is baked into the adventure design. It is something Player One's character must grapple with, directly and can even be an occasion for role play: Is he really so timid that he'll allow the Virgin Prince to be sacrificed at the top of the Ziggur-mid?