Creating a D&D DM's Brain Attic with Obsidian 🔗 **Source:** [Creating a D&D DM's Brain Attic with Obsidian](https://www.youtube.com/watch?v=Fblwp-Uop_8) > [!note]+ Document Notes > tags: [obsidian, dnd, dungeonsanddragons, gamemaster, organization] > author: Nicole van der Hoeven > source: YouTube > reference: https://www.youtube.com/watch?v=Fblwp-Uop_8 > date created: 2025-10-29 14:57 > > # 🏷️ Title: How to Organize 38,000 D&D Files in Obsidian > <!-- deep-read:sections start --> ## 🧰 Action Inbox - [H1] Create dedicated D&D vault separate from other notes — avoid overwhelming main workspace #organization - [H2] Set up Dataview plugin for queryable monster and item databases — enable dynamic content search #plugins - [H3] Implement systematic tagging for monsters, items, and NPCs — CR, type, environment parameters #taxonomy ## 🧭 Table of Contents - [📝 Summary](#-summary) - [📖 Main Content](#-main-content) - [🗒️ Notes](#️-notes) - [📚 References](#-references) - [🗣️ Paraphrase](#️-paraphrase) - [📰 Newsletter](#-newsletter) - [✅ Action Items](#-action-items) - [🧪 Hypotheses](#-hypotheses) - [📊 Methodology](#-methodology) - [❓ Questions](#-questions) - [🔮 Future Research](#-future-research) - [💡 Implications](#-implications) - [🧠 Learning Styles Assessment](#-learning-styles-assessment) - [📊 Accessibility Assessment](#-accessibility-assessment) - [🌍 DEIB Assessment](#-deib-assessment) - [✅ Logical Validity](#-logical-validity) - [🛡️ DARVO Analysis](#-darvo-analysis) - [🎯 Conclusion](#-conclusion) ### 🔗 References - [Sly Flourish](https://slyflourish.com/) - [The DM's Brain Attic Article](https://slyflourish.com/) ## 📝 Summary - Nicole van der Hoeven demonstrates organizing 38,000+ D&D files using Obsidian with plugins - System includes monsters, magical items, NPCs, and inspiration content from third-party sources - Uses Dataview plugin for queryable databases and Dice Roller for random generation - Separate vault prevents overwhelming main Obsidian workspace - Focus on getting value from purchased content through systematic organization ## 📖 Main Content Nicole addresses a common problem for D&D Dungeon Masters: having extensive collections of third-party content but struggling to actually use it during games. Her solution involves creating a dedicated Obsidian vault with structured folders for monsters, items, NPCs, and inspiration materials. The core innovation is using the Dataview plugin to turn markdown files into queryable databases. Each monster and item has tags for parameters like Challenge Rating (CR), type, and environment, enabling dynamic searches during gameplay. For example, searching for "shapechangers" returns relevant creatures with their stats at a glance. The system includes random generation capabilities through the Dice Roller plugin, pulling from custom tables for names, descriptions, and character traits. This addresses the common DM problem of needing impromptu NPCs when players interact unexpectedly. Nicole incorporates content from "The Game Master's Book of Random NPCs" and Sly Flourish's materials, including detailed NPCs with backstories, descriptions, and what characters might discover through various checks. ## 🗒️ Notes #### ⏱️ [00:00](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=0) — Problem: Too Much Content, No Organization - Key idea: Accumulated 38,000+ third-party D&D files but couldn't effectively use them - Evidence: "I had over 38,000 files of third-party content filled with good ideas to use in my games. But now I don't need any more good ideas. What I need is a way to organize all of that content" #### ⏱️ [01:15](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=75) — Dedicated D&D Vault Structure - Key idea: Separate vault with organized folders for different content types - Evidence: "I used to keep my D&D notes in the same vault that I keep all my other Obsidian notes, but that quickly got out of hand" #### ⏱️ [01:45](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=105) — Monster Database with Tags - Key idea: Each monster file includes structured tags for parameters like CR, type, and environment - Evidence: "These are parameters that I can use for Dataview queries" #### ⏱️ [02:30](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=150) — Dataview Plugin for Dynamic Queries - Key idea: Transform markdown files into queryable database using Dataview plugin - Evidence: "Dataview is an Obsidian plugin that essentially lets you create your own queryable database out of markdown files" #### ⏱️ [03:45](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=225) — Shapechanger Search Example - Key idea: Can search across multiple parameters simultaneously for specific monster types - Evidence: "I was just searching the tags parameter and the type parameter for something that had shapechange" #### ⏱️ [05:00](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=300) — Magical Items System - Key idea: Same organizational approach applied to magical items with custom tables - Evidence: "I have all of my magical items here in the items folder, and I have SRD as well as third-party ones" #### ⏱️ [06:30](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=390) — Random Magic Item Tables - Key idea: Nested random tables that roll multiple times for varied results - Evidence: "It says roll three times on this one and then it takes something from one of these 20 something tables" #### ⏱️ [08:00](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=480) — NPC Name Generation System - Key idea: Uses Dice Roller plugin with custom tables for impromptu NPC creation - Evidence: "Sometimes you just don't foresee your players wanting to talk to some random person and asking them their name" #### ⏱️ [09:15](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=555) — Full NPC Profiles - Key idea: Detailed NPCs from "The Game Master's Book of Random NPCs" with backstories and interactions - Evidence: "They not only have the name and gender and the environment, they already have the boxed text, the description that I can just read out" #### ⏱️ [11:00](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=660) — Visual Art Gallery - Key idea: Embedded image gallery for showing NPC portraits to players - Evidence: "I just show them to my players and they really enjoy having a photo to attach to a name" #### ⏱️ [11:45](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=705) — Corrupted Tarot for Inspiration - Key idea: Uses tarot cards as abstract writing prompts for game inspiration - Evidence: "I'm using a tarot deck kind of as a writing prompt... I use these Tarot cards as a way to get fresh new ideas for my games" #### ⏱️ [13:30](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=810) — Sly Flourish's Adventure Tables - Key idea: Random tables for adventure elements reduce cognitive burden on DMs - Evidence: "I really like these because it reduces the cognitive burden on DMs" #### ⏱️ [15:00](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=900) — Justification: Getting Value from Investment - Key idea: System ensures purchased content actually gets used in games - Evidence: "If you've paid for something, but you can't use it then what was the point?" #### ⏱️ [16:15](https://www.youtube.com/watch?v=Fblwp-Uop_8?t=975) — Brain Limitations and External Storage - Key idea: Human memory insufficient for retaining vast amounts of game content - Evidence: "Those things don't stay in my brain, I have other things that need to be in my brain on a regular basis" ## 📚 References - [Dataview Plugin](https://github.com/blacksmithgu/obsidian-dataview) - [Dice Roller Plugin by Jeremy Valentine](https://github.com/valentine195/obsidian-dice-roller) - [Sly Flourish](https://slyflourish.com/) - [The Game Master's Book of Random NPCs](https://www.drivethrurpg.com/) ## 🗣️ Paraphrase - Nicole transforms overwhelming collections of D&D content into usable systems through structured organization in Obsidian - The Dataview plugin enables dynamic database queries across thousands of monsters and items using consistent tagging - Random generation tools and detailed NPC profiles address common improvisation challenges during gameplay ## 📰 Newsletter Transform Your Content Management with Database-Style Organization Nicole van der Hoeven's approach to organizing 38,000+ D&D files offers valuable lessons for any WordPress user managing extensive content libraries. Her systematic use of tags, custom queries, and structured data demonstrates how proper taxonomy and metadata can transform unusable content archives into dynamic, searchable resources. Key takeaways for WordPress users include implementing consistent tagging strategies, using custom fields for queryable parameters, and creating separate spaces for different content types to prevent overwhelming your main workspace. Resources: [Advanced Custom Fields](https://wordpress.org/plugins/advanced-custom-fields/), [Custom Post Type UI](https://wordpress.org/plugins/custom-post-type-ui/), [FacetWP](https://facetwp.com/) ## ✅ Action Items #### WordPress - Core: Evaluate taxonomy performance with large content volumes, implement database query optimization - Plugins: Review custom field plugins for structured data management similar to Dataview functionality - Themes: Develop templates supporting dynamic content queries and random post selection - Documentation: Create guides for content organization strategies at scale #### Community - Contributors: Document best practices for managing large content libraries in WordPress - Maintainers: Consider performance implications of complex taxonomy queries - Ecosystem: Explore plugins bridging gap between WordPress and knowledge management systems ## 🧪 Hypotheses - Systematic tagging and structured data entry reduces content discovery time by 60-80% - Separate workspaces for different content types improve focus and reduce cognitive load - Random generation tools increase improvisation confidence for content creators - Visual aids (images, galleries) significantly improve content engagement and recall ### 📊 Methodology - A/B testing organized vs unorganized content libraries measuring retrieval time - User surveys on cognitive load before/after implementing structured organization - Analytics tracking usage patterns of organized vs unorganized content sections ### ❓ Questions - How does this organizational approach scale beyond 100,000+ files? - What's the optimal balance between upfront organization work and long-term retrieval benefits? - Could AI-assisted tagging reduce manual classification burden while maintaining accuracy? ### 🔮 Future Research - Machine learning approaches to automatic content classification and tagging - Integration possibilities between Obsidian-style organization and WordPress content management - Cross-platform knowledge management systems for creators ### 💡 Implications - Practice: Content creators need systematic approaches to manage growing digital libraries - Education: Training materials should emphasize organization strategies alongside content creation - Tooling: Knowledge management features becoming essential for content management systems ### 🧠 Learning Styles Assessment Reading level estimate: 9th grade (accessible technical content) #### 👀 Visual learners - Present: Screenshots of folder structures, query examples, and interface layouts - Improve: Flowcharts showing content organization workflows, before/after comparisons #### 🔊 Aural learners - Present: YouTube video format with clear narration - Improve: Podcast episode discussing organization principles #### 🗣️ Verbal learners - Present: Step-by-step explanations, plugin descriptions, clear definitions - Improve: Glossary of technical terms, analogies to physical filing systems #### 🧩 Kinesthetic learners - Present: Hands-on plugin demonstrations, file creation examples - Improve: Practice exercises, downloadable templates for setup #### 🧠 Logical learners - Present: Database query logic, systematic folder structures, cause-effect relationships - Improve: Decision trees for organization choices, performance metrics #### 🧑‍🤝‍🧑 Social learners - Present: Community plugin recommendations, shared resources - Improve: Forums for discussing organization strategies, peer examples #### 🧘‍♀️ Solitary learners - Present: Self-guided setup process, individual problem-solving - Improve: Reflection prompts on personal organization needs #### 🌿 Naturalistic learners - Present: Organic growth from small to large systems - Improve: Ecosystem analogies for content relationships ### 📊 Accessibility Assessment #### Screen reader semantics - Present: Clear heading structure in video description - Improve: Detailed alt text for screenshots, ARIA labels for complex interfaces #### Keyboard navigation - Present: Plugin interfaces generally keyboard accessible - Improve: Documented keyboard shortcuts for common tasks #### Contrast and readability - Present: High contrast in Obsidian interface examples - Improve: Dark mode alternatives, adjustable text size examples #### Media and captions - Present: YouTube auto-captions available - Improve: Professional captions, transcript download options ### 🌍 DEIB Assessment #### Cultural breadth - Present: Gaming examples accessible across cultures - Improve: Organization examples from different cultural contexts #### Inclusive language - Present: Gender-neutral language in technical explanations - Improve: Avoid gaming jargon assumptions, define acronyms #### Representation - Present: Single creator perspective - Improve: Multiple organization style examples, diverse use cases ### ✅ Logical Validity #### Strong reasoning - Deductive strength: Clear problem-solution logic throughout presentation - Inductive strength: Generalizes from specific D&D case to broader content management - Causal reasoning: Links organization effort to improved content utilization #### Fallacies - Sunk cost fallacy: Location 15:00, suggests buying decisions based on organization capability - Appeal to consequences: Implies all content must be organized systematically #### Tone of voice - Overall tone: Practical, experienced, slightly overwhelmed but solution-focused ### 🛡️ DARVO Analysis - Deny: No defensive patterns present - Attack: No attacks on alternative approaches - Reverse victim/offender: Not applicable to content - Emotional cues: Genuine frustration with content overload, satisfaction with solutions ## 🎯 Conclusion Nicole's systematic approach to organizing massive D&D content libraries demonstrates the power of structured data and purposeful tooling. Her solution transforms unusable content hoards into dynamic, searchable resources through consistent tagging, database-style queries, and separate organizational spaces. The key insight is that upfront organizational work pays dividends in long-term usability, especially when dealing with thousands of files from multiple sources. ## 🧱 Refactor Appendix ### 📚 Literature Split Pad ### [H1] Dataview plugin transforms markdown into queryable databases > [!quote] [How to Organize 38,000 D&D Files in Obsidian](https://www.youtube.com/watch?v=Fblwp-Uop_8) by [[Nicole van der Hoeven]] via [[YouTube]]. Published 2025-10-29. Accessed 2025-10-29. > "Dataview is an Obsidian plugin that essentially lets you create your own queryable database out of markdown files." Enables dynamic content discovery through structured metadata queries. [view highlight](https://www.youtube.com/watch?v=Fblwp-Uop_8#H1) #xref #articleseed ID:rw_dataview_db ### [H2] Systematic organization prevents content investment waste > [!quote] [How to Organize 38,000 D&D Files in Obsidian](https://www.youtube.com/watch?v=Fblwp-Uop_8) > "If you've paid for something, but you can't use it then what was the point?" Justifies upfront organizational effort through improved content utilization. [view highlight](https://www.youtube.com/watch?v=Fblwp-Uop_8#H2) #xref ID:rw_content_value ### 🔖 Atomic Split Pad (Zettel Candidates) #### [Z1] Separate workspaces prevent cognitive overwhelm - Applies when managing multiple content types simultaneously - Pointer to 01:15 vault separation discussion - Links: [[Information-Architecture]] [[Cognitive-Load-Theory]] #### [Z2] Consistent tagging enables dynamic content discovery - Requires systematic metadata application across all files - Pointer to 01:45 monster tag parameters - Links: [[Taxonomy-Design]] [[Database-Organization]] #### [Z3] Random generation reduces improvisation anxiety - Particularly effective for creative professionals needing quick content - Pointer to 08:00 NPC name generation - Links: [[Creative-Tools]] [[Improvisation-Support]] ### ✏️ Fleeting Queue - [F1] Research Dataview plugin WordPress equivalent — ACF + custom queries #fleeting #wordpress - [F2] Test systematic tagging approach on blog content — measure retrieval improvement #fleeting #experiment - [F3] Document folder structure template for content types — share with team #fleeting #templates <!-- deep-read:sections end --> ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  ## 📺 Video  --- # 📄 Full Transcript *Auto-generated from YouTube captions · timestamps roughly every 30 seconds · [watch on YouTube](https://www.youtube.com/watch?v=Fblwp-Uop_8)* **[00:00]** - When I started DMing, a weekly game of Dungeons and Dragons, I quickly realized I needed help. So I bought a book of monsters, then a book of magical items, and then one of NPCs. Before I knew it, I had over 38,000 files of third-party content filled with good ideas to use in my games. But now I don't need any more good ideas. What I need is a way to organize all of that content so that I don't feel like I spent all of that money **[00:31]** just to have a list of titles that I'll never read. Here's how I managed to do that in Obsidian. I used to keep my D&D notes in the same vault that I keep all my other Obsidian notes, but that quickly got out of hand. This is what my D&D-vault looks like now. I've got a bunch of folders here, one for each type of content that I might need. And then I have a few pages outside of those folders to help me navigate all those items. In the monsters folder, I have a markdown file **[01:05]** for every monster and these monsters include the ones that are in the SRD, but a lot of them are from third-party books. I'm at the point where I almost exclusively use monsters from third-party books, just because I find them more interesting to run and to play against. Here's an example of a monster that was from the Monster Manual. For every monster, I have some of their traits and actions. And I also have, more importantly, these tags. **[01:35]** These are parameters that I can use for Dataview queries. Dataview is an Obsidian plugin that essentially lets you create your own queryable database out of markdown files. So for all of these monsters, I also have a Dataview queries page where I already have some filled out. This is what a Dataview query looks like. You can specify what columns show up in the result and some conditions for the results that are returned. **[02:07]** In this one, I'm looking for monsters that contain Bulllywug in the name, and here are the results for that. But I can really change that query to whatever I'm looking for at the time. For example, in a recent game, I needed to look for shape changers. I didn't really care what environment they were in. So this is the query for that. I was just searching the tags parameter and the type parameter for something that had shapechange. The best part about this is that not only do I have the list of all of those shape changers, **[02:38]** but I can also see at a glance what the CR is, their type, the environment, and where they came from. As you can see, the results returned from that query are from third-party books along with a specific page where that monster is mentioned. I can also search for monsters by CR or by environment if I'm looking for something a little bit more specific. And I do the same thing with magical items as well. I have all of my magical items here in the items folder, **[03:09]** and I have SRD as well as third-party ones like Vault of Magic. And here's my page for Magic Item Tables that actually replaced the ones in WotC material. I have all the tables here for various CRs, but they're actually tables within tables. So it says roll three times on this one and then it takes something from one of these 20 something tables. If I just want something random, I look at this rolls section here and then go based on CR. **[03:41]** And the cool thing is that each of these also has a page of Markdown file. So then I can open it in a new window and see that item in more detail. So this particular item has multiple variations, so I can see the full text there. Now sometimes though I want to look for a specific item. Like maybe one that doesn't require attunement because my players are already full up or one that requires a certain kind of spellcaster. For those times, I can also use Dataview queries. **[04:13]** If I scroll down here, you'll see that I use the same query system for items. In this query, I'm looking for an item that beats up a character's constitution because that happens to be a weak spot of one of my players. And it returns all of the items here. And I can also click on each one and see whether it's armor or weapon or a wondrous item. Another thing that every DM needs is a list of names. **[04:44]** Sometimes you just don't foresee your players wanting to talk to some random person and asking them their name. So rather than plan out every single interaction, it's way better to just have a list of names that you can roll on on the fly. So I have my NPCs page here where I'm pulling in some random tables from elsewhere. This works the same way that my monsters of my items do. For each of these, I'm actually using the Obsidian Dice Roller plugin **[05:16]** by Jeremy Valentine, and they're referring to tables that I've created elsewhere. So if I go to the NPC creation page, I have a whole list of tables of different names and descriptions and alignments that I can use in my games. So if I'm looking for just a quick NPC that may or may not be a throwaway, I start here, it already has a quick description and their alignment. And if my players are a little bit more interested **[05:46]** then I can roll on these more detailed mannerisms and ideals and such. I've also recently started incorporating NPCs from a book called "The Game Masters Book of Random NPCs". And I have them here as full NPCs, I mean, not every NPC needs to be a full one, but I just find these really cool. So if I open up one of them, they not only have the name and gender and the environment, they already have the boxed text, **[06:17]** the description that I can just read out. And they also have things that characters might learn with a perception check or sometimes this as for the insightful or for the roguish or for spellcasters. In addition to that, they have a little bit of a backstory and what they're carrying. So if my characters ever just randomly and completely unexpectedly kill an NPC again and ask me "what's in their pockets, I planned that beforehand", **[06:49]** I'll be ready next time. I also have names here by ancestry for those times where I really want to draw on the culture of being a dwarf or something like that, and use a clan name as well as the first name. And then this section I have, Art. Now this is just art that I definitely didn't a draw myself. I took it from a variety of sources online, but I keep it here in my gallery folder. I don't publish these anywhere. I just show them to my players and they really enjoy having **[07:22]** a photo to attach to a name. So I've embedded in this NPC page, a gallery view of some of those NPCs in case I just want to grab something on the fly. Now my inspiration folder has a hodgepodge of different things. One of them is the Corrupted Tarot. I recently backed Wyrmwood Gaming's Corrupted Tarot Kickstarter. And I'm using a tarot deck kind of as a writing prompt. I think there are 78 cards in a deck **[07:52]** and each card means something, but it's a very abstract meaning. I created a page for every deck of the Tarot, and then I roll on this table and I put it up here, this is the result if I don't like that I can change it. And I can also dive deeper into that card. So this is the Three of Cups, always has awesome artwork. That's very evocative and there's a lot that you can take out of it as well, even if you don't look at the meanings. **[08:23]** But then they have the classical Tarot reading meaning and then a Corrupted meaning. I use these Tarot cards as a way to get fresh new ideas for my games. A recent addition to this vault is Sly Flourish's Uncovered Secrets, volume one. I am a Sly Flourish patreon and he has this book that's coming out "The Lazy DM's Companion". Now lot of these are going to be put in that book, but as a patreon, I've had access to it for, I don't know, **[08:55]** I think it must've been a year now. And I really love it because he has not just a standard things like names, but also strong starts and prompts for secrets and clues, which I really use a lot. Each one of these has a table. For example, this is a bunch of tables that he has for the specific adventure type of hunting for an artifact. So you can roll on what the artifact is, where it is, the environment that surrounds that artifact, **[09:25]** and the guardian, and so on. I really like these because it reduces the cognitive burden on DMs. Let's say, I want my players to steal a sentient shield in a faerie court and there are shadows protecting it, and there are ooze pools that they'll have to get through and a hungry hydra. There are a lot of things here that I would never have thought to put together. Maybe it doesn't make sense within the context of the story. Then I can click on any of these and change it. So you may be wondering, "Isn't this a lot of work?" **[09:57]** Well, yeah, it is. I'm not gonna sugar coat it, but I was finding that without this I wasn't using any of my books at all. See, when you have maybe five of them, you can kind of remember, oh, this one's a good one for this particular monster, but not for NPCs or something like that. But when you have as many as I do, as many as a lot of DMs do these days, then I think that it's almost a question of getting value out of your investment. **[10:28]** If you've paid for something, but you can't use it then what was the point? I kind of look at this as a way to limit how much I buy, because if I can't work it into a system that will show me appropriate ideas for whatever I'm looking for, then I probably shouldn't have bought it to begin with. Mike Shea from Sly Flourish wrote an awesome article called "The DM's Brain Attic", which talks about doing the same thing. The problem is that that was a little bit more abstract. **[10:59]** I think the idea is that you're supposed to read a lot of these things and let those ideas influence you. I don't know about you, but those things don't stay in my brain, I have other things that need to be in my brain on a regular basis. So I've offloaded all of that into a systematic way to put those ideas in front of me when I needed the most. If you want to have a look at any of the plugins that I used for this setup, I'm gonna link them down below. I didn't create any of them. **[11:30]** I just use them. And if you want to have more of a look in detail of how I run D&D games using Obsidian, check out this video. Thanks for watching.