Putting estimation behind us, we may progress into the realm of planning, which I'll define as building the framework that enables the entire game to function during play. In ancient times, when I wrote How to Run, I tried to address this by encouraging the DM to conceive of the world in terms of entities (such as factions, powers and major entities) and geographical structure... but I've since abandoned that approach for something that I hope may be more easily grasped and therefore applied.
To begin with, the setting must have earth-like features, whether or not it is a fantasy, simply because it's going to be occupied by creatures that human beings can conceive of. We may therefore dispense with thinking in terms of geography and whatever, assuming for the present that yes, those things exist, but they're not fundamental to the way we build the setting. We need to think instead about providing those aspects of the setting that are, again, essential for supporting the game's content. This isn't about creating new idea, per se, as it is about deciding which elements are important for the game to work.
We might stipulate the following core assumptions about what the players will want to do in game play. They're going to explore their surroundings, seeking out new places. They're going to engage in combat or conflict when confronted by threats. They'll have to solve problems that arise, whether these are decisions that have to be made, social dynamics that need to be navigated or conundrums that require cogitation to solve. Another fundamental pattern is no doubt going to be the accumulation of wealth, power, objects and what not. And they'll likely pursue personal goals as they're motivated to do so.
These are the base things that we need to plan for. Let's just take the first. For the players to explore their surroundings in an ordinary D&D game, certain fundamental aspects must be invented. The players will need a civilised area, such as a town, village or city, and probably more than one. Here, they can interact with peaceful, helpful non-player characters, gather information, rest and exchange for resources. Such places provide a location in which to ground themselves, a place that can be familiar, with other services and opportunities for them to be safe and pursue both commerce and relationships.
Surrounding these areas must be a wilderness or untamed area, no matter how small, to provide the essential space for players to freely adventure. This wilderness serves as a contrast to the ordered, socially structured world. Here, the players are free to move their character pieces on the gaming board without worrying about the constraints of civil law, social etiquette or status. It is a space where their choices and abilities are tested against raw, primal forces — whether that’s the threat of monsters, harsh environmental conditions, or ancient forgotten powers. The wilderness offers the chance for players to push boundaries, explore forbidden or dangerous areas, and engage in the more violent aspects of the game.
We want places of significance... locations that hold meaning or purpose within the game, both in civilised and uncivilised places. This can be some oddly beneficial facility that the players must travel some distance to reach, that gives them some special bonus or knowledge that can't be gained anywhere else. It is more obviously a dungeon. These locations aren’t just notable because they are where players fight monsters or gather loot, but because they create lasting impressions. A place of significance should alter the players' understanding of the setting; such locations serve us best when they reframe how the players think and feel about the game itself.
When possible, there's an opportunity in such locales to get into the players' heads, creating real emotional engagement and disruption — whetting their appetites for things they don't even know they want: revelations about themselves or their allies, unexpected morale dilemmas or thrills that draw them deeper into the game on a personal level. This kind of engineering isn't easy to understand, and it needs to be addressed in greater depth... for the present, for those who haven't yet seen how to do this, it's best for the present just to comprehend that the concept is out there, waiting to be plumbed.
Within the realm of the more easily understood, we should consider the basic formulas underlying the setting's infrastructure. Roads and routes for travel is just the surface. Understanding how goods are grown and brought to market, how resources are collected and then manufactured into goods, whether or not we want to pursue an economy, are details that give purpose to the workers and managers throughout the society. From there we need to understand the political framework of the world, not in terms of diplomacy or national conflict, but how authority is divided, providing the players with insight as to how the rungs of the world's power ladder can be climbed.
These tools tell us where the players can find things, and how the various facilities of the game world, from inns to castles, need to be placed and scattered throughout the setting. Much of this can be as simple as finding some basic works describing the historical period that more or less defines where the players live and what they see. From there, comprehending the function and nature of the supernatural system that underlies the game world, if there is one, helps in providing an explanation for all sorts of weird and unexpected patterns that affect our player character's day-to-day.
Some may find such "homework" boring; others may feel obligated or encouraged to pursue deeper and deeper concepts, a path that is encouraged by asking the right questions. Begin with what the thing is, then move onto how it became that way. From there, determine why it ultimately changed before our present day arrived. If it didn't change, try to understand why it didn't. When encountering an odd world, search for what it is on wikipedia or more modern chat programs. Keep at it. Knowledge accumulates slowly. As Churchill said about the accumulation of munitions, the first year you get nothing; the second year, very little; the third, a trickle... and the fourth year, a flood. The same ideal must be applied for anyone who wishes to familiarise themselves with the function of an ENTIRE WORLD. For a long, long time, it seems like a frustrating, wasted effort, and certainly nothing that can be usefully applied to a game like dungeons and dragons. And then one day, when one least expects, the knowledge changes everything about the way we run as dungeon masters.
This, then, is the basic scaffold of the setting: safe places, dangerous places and routes between them. In most parts of the world, these should blend together. Initially, it's easy to imagine a town that sits upon the threshold of a wilderness. For personal experience, we comprehend naturally that there are streets of an urban centre that are safe to walk along, and others that should not be ventured into, especially at night. Anyone who has stayed overnight at a seedy hotel recognises there's good reason to hesitate before knocking on some stranger's door, or even speaking to persons in the halls. No place is entirely safe; likewise, there should always be places in the wilderness, even in the heart of a dungeon, that are justifiably "safe," even if magic is needed to make them so.
This blending of elements makes the world feel more organic, less compartmentalised... and therefore, more immersive. This creates an environment that keeps the players on their toes. A fusion of elements reinforces the setting as a volatile, active place, like a set of chemical reactions on the verge of occurring, perhaps set to explode when this slow moving green stream actually reaches that small blue pool. Knowing what happens increases the intensity with which we'll watch the event unfold — it is this precise design that we want to incorporate into the fabric of things going on around the players as they gawk about. This designing of tension into the setting is as important as any other element we want to incorporate... which is accomplished by understanding that things around the player are not standing still. Like the dangerous stream moving towards the safe pool, the setting is in motion.
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