I have been using my downtime system, published in Downtime in Zyan and originally presented across my blog Mazirian’s Garden, for my face to face dreamlands campaign. This is a game with a stable group of 4 players rather than a bigger open table game. Over this campaign and my previous one, which also have shrunk to a 4 or 5 person group of stable players at the higher levels, I've discovered a tendency that undermines the use of downtime over time. I think it's a tendency that arises in games where the initial default at low levels is short jaunts to perilous adventuring locations--getting into and out of a dungeon in one or two sessions. In that context downtime as I've designed it works very well.
On my system, each character gets one downtime action between adventures from a large menu of freeform options. It involves a 2d6 roll with base and situational modifiers. Generally, there's a tracker with a certain number of steps to complete the project. A 7-9 is a mixed result that often requires one to adventure to make progress or eliminate an obstacle. A 10+ is a straightforward success. The general idea is that in a game relentlessly focused on cooperative play, downtime allows player characters to pursue their individual dreams and leave their mark on the campaign world starting from the end of their very first session.
In online games I handled downtime actions in discord between sessions. This was fun, because you could prep and go deep with downtime, dropping tons of lore or colorful NPCs. But sometimes it was hard to corral people to do downtime between sessions, and I very often found myself failing to "do my DM homework", which sucked the air out of downtime. In face to face games I've found it works better to resolve downtime at the start of a session in about 30 minutes at the table without much prep on my part.
Here's how I start that 30 minute period. I have a system of tables for campaign events, along with some clocks that get triggered by past player actions. So I start by telling them the campaign news to give them something to react to if they want to, which every once in a while includes a threat that needs to be dealt with in downtime or the opportunity to perform time-sensitive downtime actions. Then I remind each player of all the downtime actions they had going in the past. Without keeping notes about this and reminding them what they've been doing, I find that they leave a ton of loose threads and have trouble remembering what they had going. This really diminishes the significance of downtime. But with a little reminder of what they've been up to in the past this problem vanishes.
I then move around the table to have them declare downtime actions. I then begin resolving the actions. I find that I weave between different players as they resolve the actions, switching the spotlight at dramatic moments. They often advise one another or make creative contributions along the way, so people stay pretty engaged. This makes for a very dynamic 30 minutes that players look forward to as a reward between adventures. But the main point is that it doesn't involve very much homework for me at all. Sometimes I think for about 15 or 30 minutes before the game about it, but sometimes I don't think about it at all. Everyone understands that it's more freeform and improvisational than the sessions we're running, and I think they like that rhythm of the more structured adventures and the more improvisational downtime.
The problem I've identified is that as the party rises in level, and gets invested in the campaign world, they start going on longer and longer adventures. What was once one or two sessions in the dungeon becomes six or seven sessions of hex crawling, or city crawling, or hopping between three different adventure locations to accomplish some multi-part mission. I could try to stop this but I wouldn't want to because it feels organic and allows us to play a deeper game driven by more ambitious player objectives. This means that downtime diminishes in significance to a nearly vanishing point since it happens so rarely. People feel disconnected from their projects, which feel impossible to finish anyway. Downtime decreases in importance precisely at the point where it should matter the most, when the player characters become increasingly invested in the campaign world, and ought to care the most about accomplishing self-invented projects.
My new solution to this problem is to grant the party multiple downtime actions after a longer adventure. The thin rationale is that if an adventure takes 4 or more sessions to complete, then the characters need a longer break and may take an extra downtime action. I've found this double downtime action solves the problem. The difference between 1 and 2 downtime actions is noticeable in play. It allows each character to pursue two different dreams at once, or to suddenly make a lot of progress on one project. Each downtime feels like a big deal. Given that downtime is happening less often, I think it really helps to keep them invested in the downtime phase.
When they've just come back from a six or seven session adventure, it also creates a lovely feeling that we're closing one chapter and opening another. (This solution is, by the way, related to the idea of using downtime to model a larger campaign hiatus that I discussed here.) In an anarchic game that is a player driven sandbox without narrative arcs or discrete planned chapters, this is a nice organic substitute
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Could you give some examples of what free-form options you provide? I am always afraid I will be insinuating a skill or objective is Important by presenting it to a player without them first broaching it but I feel my players are left without an idea of what projects to ask for. They know learn new languages, practice with a new weapon but the larger political or social aspects don’t come up.