how to portray long or difficult tasks in an interesting way?

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I run my campaigns pretty sandboxy and without much prep. I let the characters decide what they want to do, so I can't plan flowery language and interesting what/if scenarios for every situation. Usually I'm pretty good but there's one situation that I always fail.

The long, challenging, and sometimes mundane task, especially when I want the PCs to succeed.

Crossing a desert, looking for a hidden encampment, tracking an enemy, researching in a library, etc.

I've tried to throw together some skill challenges on the fly, but those haven't been any more exciting really. Since I want the PCs to succeed, its hard to determine failure penalties, and I hate the "lose a healing surge" penalty.

I suppose I could describethe situation and be sure to mention the challenge, but I'd rather find a better, more interesting way to improve my DMing. Especially to get the PCs involved more.
The long, challenging, and sometimes mundane task, especially when I want the PCs to succeed.



That kind of stuff shouldn't get screentime. Describe what happens, ask for input, jump to the next scene.

No amount of tips, tricks, or gimmicks will ever be better than simply talking directly to your fellow players to resolve your issues.
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That's what I've been doing, but I always feel guilty like I'm taking the easy way out. Something like crossing a vast wasteland where the harsh conditions are as treacherous as any monster kind of sucks to gloss over. But if I can't make it play interesting that is probably my best bet at this point.
That's what I've been doing, but I always feel guilty like I'm taking the easy way out. Something like crossing a vast wasteland where the harsh conditions are as treacherous as any monster kind of sucks to gloss over. But if I can't make it play interesting that is probably my best bet at this point.



I know what you mean. But unless you can think of a really good reason why it's awesome and make it so, skip it. Better yet, come up with a series of evocative questions that you don't need to know the answers to, ask them out loud, and let your players tell the story for you. If somebody says something that might lead to an outcome that could go either way, ask for a die roll and narrate the results based on the roll. Take whatever is particularly interesting out of what they give you and make a note to build on it later.

You'll probably get better results that way than try to shoehorn in a skill challenge because you feel you need to.

No amount of tips, tricks, or gimmicks will ever be better than simply talking directly to your fellow players to resolve your issues.
DMs: Dungeon Master 101  |  Find Your GM Style  |  Structure First, Story Last  |  No Myth Roleplaying  |  5e Monster Index & Encounter Calculator
Players: Players 101  |  11 Ways to Be a Better Roleplayer  |  You Are Not Your Character  |  Pre-Gen D&D 5e PCs

Content I Created: Adventure Scenarios  |  Actual Play Reports  |  Tools

I'm Recruiting Players for a D&D 5e Game: Interested?  |  Follow me on Twitter: @is3rith

Iserith's suggestion is good, but it's going to require the players to be interested in the survival scenario.

If they aren't interested in roleplaying wilderness survival, then skip it. Your best bet for showing how dangerous the trip is is to create an actual encounter that they run into. For example, maybe a sandstorm forces them into a cave system, and they have to deal with the denizens there. Maybe they get lost in the fire marshes and have to make a deal with a hag to get out. Think of a couple things that can go horribly wrong while they're traveling, and create encounters out of them. That beats a generic "roll your third endurance check" skill challenge.
it's going to require the players to be interested in the survival scenario.



True. This can often come down to how you frame the questions. For example, "There is a black cloud on the horizon. What do you do?" is not nearly as interesting as "There is a black cloud on the horizon. What do you think it is?" Then roll with whatever the player says. Let's say he says it's an approaching army, far off in the distance. Immediate followup with a yes/no - "Is it coming this way?" Get the answer.

Next open-ended question to another player: "What rumors have you heard about this horde?" Let him answer. Follow up with another yes/no. Keep expanding upon it until there's either a threat or a resolution and escalate or fast forward from there, respectively. Make a note of anything cool for use later after you've had some time to think about how to incorporate it better.

I will note, however, this isn't for every type of player out there. Don't force it if they aren't into it. I've gotten some amazing results and ideas using this method. Most players I've encountered really get into it and love to see their ideas implemented this directly.

No amount of tips, tricks, or gimmicks will ever be better than simply talking directly to your fellow players to resolve your issues.
DMs: Dungeon Master 101  |  Find Your GM Style  |  Structure First, Story Last  |  No Myth Roleplaying  |  5e Monster Index & Encounter Calculator
Players: Players 101  |  11 Ways to Be a Better Roleplayer  |  You Are Not Your Character  |  Pre-Gen D&D 5e PCs

Content I Created: Adventure Scenarios  |  Actual Play Reports  |  Tools

I'm Recruiting Players for a D&D 5e Game: Interested?  |  Follow me on Twitter: @is3rith

Tell them how much resources it will cost them (very roughly). Let them elaborate on how they will save their stuff.

When I say resources, I am talking about things like: missing ropes, torn up tents, dropped trail rations, ruined clothing, lost tools, minor coin spent buying directions or for services, horses traded, public opinion, time; nothing that will interfere with the party reaching their destination, but could have consequences later on.

For best results, make a random table for what they lose and come up with a scenario in which they might lose it.

Example 1: Party is crossing the desert, you roll *rations, and decide that this means one of their waterskins developed a leak. The party decides to salvage the water by splitting it amongst their partially filled water skins because they can't stop to repair it. They could decide it doesn't matter, since the party cleric has create water and won't run out soon. Next you roll *lodging and decide the harsh desert wind whips up. The party decides to keep going and the party's tents get shredded by the wind. They could have decided to seek shelter and not damaged their tents. They could have used rope trick, or any other magical shelter.

Example 2: Party is researching in a library, you roll *rations, and decide this means they find their hunger greatly increased by the long hours of research and their food is being consumed at a greater rate. The party decides to send someone out for food, since it will be cheaper than eating all their rations. They could magically decide to make food. Next you roll *lodging and decide that party's innkeeper says that he will kick them out unless they are quieter when they come in at odd hours. The party decides to speak to the innkeep but bungle it up pretty bad, and the next day the innkeeper apologetically asks them to leave because they are disturbing his other guests. They might have decided to use stealth when returning home, or cast silence on themselves. They could have decided to move out on their own accord. 

 
WARNING: This will slow down your game and isn't all that exciting, but it might provide some roleplaying opportunities to some of the players.

I know that some of my players will do everything in their power to hold onto their stuff, however mundane. At the very least they will have something to tell the shopkeeper when they go to resupply. 'Golly, Lothgar, you look pretty beat! What happened to ye?'  'Ah, it's notso bad mate. I will, however, be needing two more lengths of rope and ya know, I think one of dem climbing kits...'
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I guess my issue is doing these things "on the fly" since I may not have planned for them.  Obviously, if I plant a quest seed that has them traveling through a dangerous environment, I can plan accordingly.  That was probably a bad example.

Thanks for the insight though, I'm going over some of the bumps that I've encountered recently, and I'm seeing how I could have skipped them, or ad-libbed differently.
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