Turn Travel Into Fun Setbacks – 3 Ways

Roleplaying Tips Newsletter #1219

Brief Word From Johnn

We played session #5 of Basilica yesterday. The old memory muscles for Basic D&D slowly return, as does the OSR mindset, which I’m really enjoying. It’s wonderful not turning to the rulebook every time to figure out what to do or how to adjudicate a player action. Instead, you weigh the current context and say no, yes, yes with a cost, or ask for a roll.

I love crunchy systems, but I’m so glad to have an Old-School Essentials campaign going to help me re-build my GMing muscles in different ways.

We did a Stars & Wishes retrospective again yesterday, and feedback included:


  • Enjoyed roleplaying with elven factions
  • Enjoyed interesting roleplay situation when the cleric robbed a fallen elf warrior (three votes)

My takeaways here are a) the players seem to be enjoying the roleplay stuff and I don’t need to cut back or change it up; b) more world building to beef up faction play a bit as that resonated.


  • More treasure
  • More elf faction play
  • Keep up the current pace of play
  • Streamline combat a bit more

Something new last session was using Campaign Tabletop, or CTT for short. CTT is a simple virtual tabletop that Jochen’s team built for Wizards of Adventure. It’s mantra is KISS. With just the essential features such as tokens, maps, fog of war, and chat, the tech fades into the background and you can freely run online sessions without most of the technical encumbrances.

Pictured above is a battle the party had with a huge boar suffering from some kind of corruption. I’ve got the token library open on the right as part of the GM-only toolset.

Anywho, I think we’ll switch from Google Slides to CTT now as token management is much better for players and GM. We’ll still use Google Slides for character sheets, player handouts, and various campaign reference material.

Due to Christmas, we play next in early January. I can’t wait!

In This Issue

  • Feature Tips: Turn Travel Into Fun Setbacks – 3 Ways
  • Reader Tips of the Week
    • Getting the Party Together
    • Gathering Up the Heroes
    • How to Plan Out Mega Dungeons Fast

How to Plan Out Mega Dungeons Fast

Turn Travel Into Fun Setbacks – 3 Ways

From Jonathan Hardin, sojournersawake.com

Stolen, Lost, and Damaged Items

Nothing is more frustrating than an uncomfortable trip — except also losing your luggage in the process. Add the potential of thievery and damaged goods during transportation and trips become tricky fast. While making character lives miserable is not the point, losing inventory means offering a new challenge on top of the existing quest. We can increase the difficulty level of each encounter by risking stolen, lost, or damaged items:


Players are not the only ones with a stealth bonus. Design a travel from one side of the town to the next and place intentional pickpockets. Hint: don’t let players know what is happening and roll in secret. Most pickpockets and con artists are smart and use their environment to prey on victims.

Pickpocketing can quickly turn into a chase or combat scene, so use this as an opportunity to link your adventure to that encounter.

[Comment from Johnn: We could also use stealthy monsters and beasts for theft encounters in the wilderness. For example, dire squirrels might sneak into camp and steal food and shiny things.

Another idea is reverse theft. An invisible or stealthy foe plants false evidence or stolen goods on the person of a PC to be discovered by guards who receive an anonymous tip…]


It is hard to find good help. Traveling on railways, carriages, and airlines risk the luggage becoming lost due to well-meaning but poorly paid and incompetent NPCs. With a quest pressing upon the player’s attention, they might have to go on without some important items.

[Comment from Johnn: Great idea! I’m running a caravan travel sequence right now in my campaign. I could have something fall off a cart, an NPC leave something important back at yesterday’s camp, or temporarily misplace something.]


Contents may settle during travel. Any potion could have a shelf life. Fragile items might break during a bumpy cart ride. Delicate tools might bend or worse when a PC takes falling damage. Rations might spoil. Pests might destroy perfectly pressed diplomat’s robes. Weapons may require maintenance. And water can damage the whole contents of an explorer’s pack (especially salt water).

[Comment from Johnn: This is a great list of troubles. I’ve enjoyed camping since I was a Boy Scout and can attest to how the elements ruin things. Even storage becomes a hazard from the act of freezing and thawing over seasons that weakens tough materials and parts.

I especially like the idea of dire squirrels eating holes through everything in their quest for food and shinies. Every GM needs some dire squirrels in their campaign.]

Keep it Fun with Rules

Our goal with these challenges is to encourage new and interesting situations and puzzles for players. We want to encourage players to think outside the box when solving upcoming problems, and Stolen, Lost, and Damaged items can spur that type of gameplay quite well.

We don’t want to disable characters so they can’t do anything on their turn. But we should signal to players in advance that they might have a problem losing their “stuff.” So hint that, along with character death, lost and damaged goods can be a real possibility.

To keep lost, stolen, and damaged items from becoming a pain at your table, design a travel hazards table. Roll at random during each hour or day of travel to determine if this unfortunate fate befalls the characters.

Here’s a example table. Roll 1d6:

  1. Pests eat 3 days rations – but you have never seen 6 legged rodents.
  2. The elements damage your weapon, reducing their efficacy.
  3. An NPC “lost” your luggage during check-in. Apologies from the manager.
  4. An unseen presence lifts your coin purse.
  5. The broken cart causes your mining equipment to tumble down the ravine.
  6. Even help can be of no help – your assistant forgot to bring your quiver.

More Storytelling Mechanics

If you are all aiming for a story, then using these complications as story points can bring excitement to the table. Notice in the table examples above how I attempted to create a mystery alongside the problem. Not only rats ate your food, but six-legged rats. It’s a simple tweak, but can help players remember that this is a fantasy world and no problems are directly aimed at the characters.

To keep the game fair, use story point tokens and designate a certain amount per game – some the GM can use and some the PCs can use. By using a token, the GM then has license to introduce a potentially frustrating element in the game — losing inventory.

Avoid allowing single cell encounters that exist within their own universe. A stolen item can be disappointing, making the players feel like they are losing the game. But if you connect it to the quest, plot, or story, then players will feel like everything matters in game, including their reactions to this setback.

May your story continue!

Reader Tips of the Week

Tips, ideas, and inspiration from your fellow RPT GMs.

Getting the Party Together

RPT GM R asks how to herd the cats:

I had never had any RPG experience until I picked up a game marked as “for all ages” (thinking it should be pretty easy to pick up) called Magical Kitties Save the Day. So, my first experience has been as a GM…and I have never felt my lack of creativity as keenly before.

Aside from learning how to structure an adventure, one big issue I’m running into is gathering the ‘Kitty Krew’ for an adventure.

The way the world is structured is that the kitties have a human and live with them. They have a special spot in their home that the humans can’t reach and it allows them to get in and out of the home without being seen.

Since the kitties can be at any given place in the city at any given time, how do you manage to get everyone together? And how do you create a hook that would create the interest for everyone that would cause them to gather?

I mean, in your post on creating hooks, you use examples that target a single person; thrusting and envelope into their hand that has their enemy’s name on it, a merchant pointing to a person to have them arrested for stealing, etc. What in those hooks encourages them to seek out their fellow party members if they aren’t with them?

The game came with a starter adventure where one of the kitty’s humans has gone missing, having gone to the library and the misguided good witch librarian had placed them in magical books that had pocket dimensions. It suggests to have all of their humans go missing if this is their first adventure to make it easier to gather everyone at the library, and there are clues provided to lead them there. But all of that takes place before the actual adventure even begins.

Though we did have everyone’s humans go missing, it didn’t give any information on how to lead the others to the library if only one of their humans had fallen victim to the librarian’s trap. Even if one of the kitties decides “this is a job for all of us” how do you get the word out? And how do you make it fun rather than tedious? Any input would be greatly appreciated.

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That sounds like a fun game. Here’s what’s worked well for me in the past:

  • The GM narrates how, where, and why everyone is together. And then you start the session. I do this a lot. The idea of happy circumstance is great, but it does not work well for our medium where players can make choices. So I just tell them.
  • Ask players to tell you. The reverse of the above. This could work well because everyone knows your modern-ish setting and could collaborate, as opposed to some dark fantasy world they know nothing about.
  • Solo pre-sessions. Each player gets private time with you to tune their character and play out recent events that have brought them to your session starting point. “I need to end with you reaching the library. Okay? But let’s start with where you were born. Any ideas?” These are great, but can become time-intensive leading up to a first session.
  • Secret backstories. You give them a public reason for being with the other PCs, but you give them a secret mission, too. This makes almost any kind of contrivance acceptable, because there’s a secret motivation to meet and group together, so any public/surface reason is usually sufficient.
  • A mysterious event. Like moths to a flame, each PC gets attracted to the campaign start time and place because of a special event. Perhaps they all had the same dream. Or a patron in a mask hires them. Or each character is handed a business card with a time and address written on the back.

I hope there is an idea in that list that helps you out.

You might also check out these tips on “The Party Unification Event” for more ideas.

And a few specific ideas:

  • A previously unknown feature of their collars alerts and guides them. Maybe there’s even a “this collar will self-destruct in 5 seconds” at the end.
  • Cat whistle. One only cats can hear, and certain ones at that.
  • Each gets a letter from their human who suspected something and created an insurance policy in case their suspicions were true.
  • An agent of the villain summons them – but as an ambush.
  • A mysterious rat offers mentorship in exchange for help defeating a great evil.

Gathering Up the Heroes

Wizard of Adventure deadshot2021 asks a similar question:

I am about to start a new 5e campaign in Ptolus. My players want to do their own starts so no one knows each other. I have two who have grown up in the city and two that are newcomers, but one is coming by land and one is coming by boat. I am really struggling with a way to gather the heroes in a way that makes sense. Any ideas?

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For getting the group together, I like to begin with the end in mind. Creating a quick plotline makes some options better than others.

Some random ideas:

  • Press ganged => gives them an instant goal and early villain.
  • Lottery => They each won the same opportunity.
  • Volunteer => Help wanted!
  • Esoteric => Shared dreams, divine intervention through signs, or some other inexplicable connection.
  • Quest => In medias res, they’ve all come to Ptolus for the same reason: deceased relative mentioned them in their will, invitation to a party or special event, subpoena, etc.

I hope this helps! If not, please let me know.

How to Plan Out Mega Dungeons Fast

RPT GM Maurice asks:

I’m currently working on a Dark Souls/Elden Ring style campaign, and I’m trying to figure out the best way to make a more freeform style mega dungeon without fully mapping out 15+ areas.


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5 Room Dungeons are a fantastic choice for that.

I’ve done megadungeons using 5RDs and they work awesome.

My rough recipe:

  1. Figure out the theme, backstory, villains, most valuable treasures, and purpose(s) of the megadungeon.
  2. Sketch out the levels or broad areas of the megadungeon.
  3. Give each area a strong gameplay and visual theme so players know when they’re transitioning to a new area and to keep the game fresh over time.
  4. Split each area up into sub-areas. For example, the lava area might have a huge lava chamber, a river of lava, a maze-like area of old dry lava tubes, and an exit to a caldera and lake on the surface.
  5. Some areas become single 5RDs and some areas I split into multiple 5RDs.
  6. Start outlining encounters — 5RD “room” encounters and standalone encounters.

That’s how I generally plot out my large crawls using 5 Room Dungeons. Then it’s a matter of adding details to areas and encounters.

To your mapping point, I draw thumbnails of maps first. These are just blobs on paper about 3 inches or so wide. It takes only a minute to make a thumbnail sketch.

In 10 minutes, I’ll have several improved iterations and a really good idea of the position, shape, and size of each area.

Combined with my plotted outline above, I don’t need map details for anything other than where the players might explore next session. Yet, I have developed the 10,000 foot view of the megadungeon to prevent collisions and logic errors.

I hope this helps!