Trying out a "Wiki" approach to story writing

I've been thinking about how to better organize my thoughts when it comes to writing stories and keeping track of a lot of information about characters, places, and events. My habit has been to write everything in a single large document or multiple large documents. Lately, though, I’m finding it difficult to focus on writing when the document is so large. I spend more time trying to figure out where to put the information and how to find it again when I should be spending more time coming up with the story and creating/editing information.

I’ve been having a similar problem with my local D&D group, for whom I am trying to create a Planechase-type story where a friend wants to play a Naruto character, another a Digimon character, and so on. The basic idea is to treat different “multiverses” as different planets in Star Trek. I have the overall idea of what I want to do, but keeping myself organized is proving difficult, especially as I make revisions to the story on a regular basis. The biggest annoyance I have is trying to connect the information in such a way that I avoid overcrowding my plot document with world-building info or character info.

Conversations with my D&D group and casual Internet browsing have got me interested in doing things similar to how Wikipedia organizes information: the website has articles that focus on a single concept and contain links to other articles. In this way, I would be able to have easy access to articles about characters, places, and events, but also be able to jump around my notes a lot more easily and potentially revise information about the story more easily. Thinking ahead, such a method may assist my future world-building efforts as I expand existing stories.

The skeptic in me says that I technically do all this already by creating different documents and better managing my folders. I could, but I really like the ability of wiki-like tools to automate some of the organization and “linking” of my various documents.

With that in mind, I’m going to give Obsidian MD a try as I write the Finding My Way (College Drone) story. I plan to spend a decent chunk of my time this month setting up Obsidian and putting together as much of the story as I can. I am definitely rewriting the first chapter based on the excellent feedback I have received, and I will let you all know later this month how that effort is going as I play around with Obsidian.