Since I announced that I was hoping to avoid going back to work as a teacher, I've been doing a lot of thinking about my role in the Obsidian community and more importantly, what I want that role to be in the future. As is often the case, chatting with Nick Milo gave me a lot of clarity about myself, my methods, what I excel at and what would be a poor use of my time.
I feel a little weird putting it all out here like this, it feels a little self-aggrandizing, but I think Nick is probably right (as he often is): the work I'm doing "behind the scenes" is important to the community, not as obvious as I thought it was, and the more y'all know about it the more you can help me do more of it.
First, some context that might be surprising to those who have started using Obsidian in the last year: I didn't originally join the Obsidian discord because I was looking to take better notes. I never really intended to take notes on things I read at all — I was looking for a way to organize research materials relevant to my stories. To be perfectly frank, most of these "notes" were emails, articles, and youtube videos.
I wanted to keep my notes connected to the stories they inspired.
So, I already knew what I wanted; I wanted an app that let me write stories in a clean, distraction-free way, while also letting me connect my research (in all its myriad, messy forms) to the places I used it. When I wrote a story about butchering a wyvern, I wanted my notes about best practices for butchering crocodiles to be nearby without cluttering things.
I tried Mediawiki first. It was a timesuck, mostly because functionality I considered basic — things that every Wikipedia page seemed to feature — were actually very difficult to implement, even after I tried paying professionals for help. I get the impression that it's become a pretty tangled project, and some critical chunks have wound up abandoned or poorly maintained. LegendKeeper was nice, but it required a monthly subscription and I didn't always write every month — when I did I could never predict when. I like "owning" my data because I have a very cyclical work pattern, and spend a lot of time on questionable wifi.
I had never heard of "personal knowledge management" apps like Bear or Roam. OneNote drove me nuts (I use it for work) and Evernote never really solved any of my problems the handful of times I tried them. I mostly used software geared for writers, things like Campfire and WorldAnvil and Dabble and Novlr... and, of course, Scrivener.
The Scrivener paradigm wanted me to put all of my notes into a tiny box in the right-hand corner, which quickly filled up and became hard to sort between ideas and match individual notes with particular paragraphs or concepts. Wikimedia had a pretty horrible writing experience. LegendKeeper wanted money (not unreasonably, but I didn't use it enough to justify the cost) and wanted to keep my files in the cloud.
I used Scrivener for years, but it never felt quite right. I thought things would improve when they rolled out the Windows beta intended to bring it up to feature parity with the new and improved Mac app, but it dragged on. Each month I had to go through a laborious update process on a monthly basis — which was sometimes every time I opened the app. I also had trouble with exporting my metadata and files. Overall, it was just a very frustrating experience.
Even before I tried the beta, though, Scrivener had never been a particularly good place to store my research — my custom metadata always felt awkward to get at, the interface was slow, and actually exporting things to use always felt cumbersome.
None of the options I found before Obsidian felt good.
I won't lie and say that I latched onto Obsidian as soon as I found it; it had been presented to me as a tool people were using to version control their stories, and git branching isn't as useful to the way I write as it is for the person who originally shared it with me. But I kept coming back when I hit a pain point with another app, trying to get a sense of it. Eventually, I found the Discord server and things started to make sense.
Obsidian seemed like it could solve my problems, but it wasn't designed for my use-case, so I spent a lot of time in the early days explaining what I was looking to do while people made suggestions about workarounds and plugins I could use.
Eventually, I learned about notetaking methods like PARA and LYT and Zettelkasten... but to be honest it was with the same part of my brain that was also learning about the API and CLI and regular expressions. I was learning by osmosis because it is my habit to "keep up" with communities I become involved with so that I can understand the unspoken rules, avoid embarrassing myself by asking inappropriate questions, and make myself useful.
I try to give more than I take from communities I join.
Anyone who hangs out with me in Discord or on Twitter for more than a few weeks will swiftly come to realize that I am basically a walking edge case. I run into weird problems. I break things. I have unusual needs when it comes to technology, and that inevitably means that I will eventually need help.
For me, the best way to get help is to be helpful. Plus, it must be said, I like being helpful — it makes me happy. So when I saw a question that I knew the answer to, I tried to take the time to answer it, both because it was an uplifting positive interaction but also because it made me feel less guilty when I inevitably asked my own questions.
Over time, I developed and refined my own system of notetaking, yes, and answered many questions about organizing notes, and even wrote some articles in response to frequently asked questions — but I also designed and built my own plugin. Patched together the pieces of my own theme. Advocated for features I felt were important for making Obsidian useful for people like me; storytellers, worldbuilders, amateur researchers.
Most people — even those who interact with me daily — see my role through the lens of my workflow showcase videos, or with the Roundup. Obviously, both of them are important to me, but I realized, talking to Nick, that many people don't realize just how deeply reluctant I am to formally teach a "system" of notetaking... and not because of anything like imposter syndrome or feeling like my system is insufficiently mature or whatever.
It's not just that I don't want to compete with Curtis or Nick or Bryan or Tiago in terms of courseware or even YouTube presence — although I very much don't; I am a writer, not a video editor, and I want to play to those strengths. If I wanted to teach in that way, I could just as easily do a newsletter drip campaign like David Perell, with daily tips and guided lessons to help people. Maybe one day, I will.
My passion is serving this community as a liaison, though.
There are many people who hang out in the Obsidian community because they are searching for something other than educational materials about notetaking or even how to use particular plugins and what they're for, actually. The Youtube content and tutorials the community has produced are incredibly valuable and I'm glad they exist, but they aren't everything that's needed.
Many folks are here because helping people is more fun than doomscrolling Facebook, or because there's actually a neat little community forming around the idea of hypertext storytelling, or for help finding good academic software... and I want to help those people, too.
If you want to know which plugin developers are interested in being hired? That's not the kind of thing that belongs in a video guide. Who's in college, who's a consultant, who's working for a FAANG company and just does this as a hobby? Which devs actually use their plugins, vs. which plugins were built as a thought experiment or a favor? That kind of information isn't generally written down in a guide — it changes too fast, and it would be a really weird invasion of privacy and violate the social norms of this community in a pretty ugly way.
But it helps to know which community member is a lawyer or a teacher or a machine learning researcher when somebody has a question about how to use Obsidian for a similar use case. When somebody needs a plugin built, it helps to be able to identify a similar but not-obvious use case that could help that plugin be useful to many more people — and increase its likelihood of being built.
And, later, of being used.
I help different parts of our community communicate.
One of the things that (I hope) sets the Roundup apart from other "link list" or "curation" style newsletters is that I make an effort to explain what each link is for. I don't just organize the information (although I also do that), I take the time to figure out what pain point each plugin is solving — something that is not always obvious from the descriptions at first glance. Developers don't always 'speak user' and users don't always know how to explain what they need or why they need it in a way that showcases the value of the requested feature. I try to help solve that problem.
I don't prioritize teaching my system because my goal has always been to help people find a system that suits their needs. I do this by showing them what other people like them have done, or helping them see plugins intended for a particular use in a whole new light — whether it's using "Fantasy Calendar" as a publication scheduler... or requesting an expansion to a plugin designed to make PDFs more readable but that, with the addition of a few more lines of code, allows for importing from other sources, as well.
I connect developers with use-cases, but I also do my best to help developers consolidate effort — reminding people of good opportunities to submit pull requests instead of making new plugins from scratch, for example when
@javalent added "readable line width" functionality to Hotkeys++
I try to help people save time.
I mentioned this in my article about fostering healthy communities, but one of the most important things about the Obsidian community is that people aren't punished for asking questions. Personally, I prefer it when someone asks me a question that takes me 5 seconds to answer than spend hours futilely sifting through resources that may or may not directly address their specific question.
Yes, obviously, I encourage people to read the documentation and check the hub and run a quick forum search, but I also recognize that not only is personal knowledge management personal, but that Obsidian is endlessly flexible and that sometimes, the most efficient way to solve a problem is to throw money at it.
One thing I didn't realize until I started the Roundup (and even more when I opened up my calendar for consulting work) is how many businesses and business leaders are interested in leveraging Obsidian — and not just for things like internal documentation. Obsidian is a powerful knowledge base that has powerful options for interoperability, which other tools can connect with.
I really believe that I've helped companies like Readwise better serve our community, by offering them a better understanding of what Obsidian users want — which is not always the same thing as what I, personally, want. As someone who has read every single message in the Obsidian Discord for the last year, most everything posted to Reddit, and a fair amount of the Twitter discourse surrounding this tool, I think I have developed a pretty good understanding of what this community's core values, interests, and needs are.
I think this is why so many people developing tools in adjacent spaces have reached out to me and asked for my insights about how their tools can be useful to Obsidian users. It's the kind of thing that happens "behind the scenes," but it's important the same way that project managers for tech companies are — no, I don't write the code, but I keep up with the updates and I monitor what's going on, and I communicate key details to relevant people.
I love helping developers help this community.
But if you don't have direct access to my personal calendar and don't hang out in the plugins channels of Discord or trawl my GitHub issues history, you might not have known.
The Roundup itself is in many ways a byproduct of the work I do to keep up with what's going on, so I can help nudge the development of the Obsidian ecosystem in ways I hope are beneficial for us all, by connecting people who might not have known about others working on similar projects, with similar interests — and complementary skills.
It's never been my goal to teach people my system.
I do, of course, try to answer questions about systems helpfully, and sometimes I have insights from my own methods that help people. When I think I have important insights that are contrary to a dominant strand of discourse, I try to bring attention to the "counterculture" voice. I try very hard to avoid repackaging and regurgitating things other people are already explaining well.
Also, I recognize that my system is designed for a relatively unique use case — it was built from the ground up to facilitate a project that very few other people are actually trying to do, namely support a complex fantasy world that can be leveraged to teach people about ethics, history, philosophy, science.
I leverage stories as an entry point to education. I work hard to break out of traditional, Eurocentric paradigms of storytelling, which also means that I mostly write fiction so short that only a handful of markets are willing to publish it, much less pay for it.
Teaching you all how to use my system in its entirety would be utterly pointless; most of you aren't doing what I'm trying to do, you optimize for different things. It would, in some ways, be a complete betrayal of everything I ever wanted to do with Obsidian, and furthermore, it would fail — because Nick Milo already has the first mover advantage and is already doing everything I want done from a "teaching people" perspective.
I would not be good at creating video-based content.
The best teaching models behavior to be emulated.
I think one of the reasons people suggest that I do a course is because I'm a decent teacher and I've demonstrated that I have the skills to teach useful things. I'm proud of my community talk about leveraging Obsidian for managing written projects, and I'm proud of the work Nick and I did to demonstrate effective ways to highlight and annotate and use those highlights and annotations in actually synthesizing thoughts.
It's easy to look at those successful moments and want to replicate them, expand them, do more with them, but the truth is, there are limits to teaching critical thinking and creative problem-solving that way, because it's one of those things that is best learned when it's modeled and when people have a chance to implement the principles on their own projects.
To be blunt, I have a toddler; I can't put in the kind of time that Nick does to teach the way it should be done; with engaging, project-based, collaborative sessions that leverage self-paced work and flexibility. Further, I don't have the skills to make the video content enjoyable to consume.
I may one day put together sample vaults for different use-cases (although my vault in its entirety is available for purchase). There are many other ways I hope to help. For example, I've seen some communities put together orientations for new users. If I find more time, I'd like to do the same — if only to get better perspective on what new folks struggle with.
Access to a wonderful multitude of perspectives is what I value most.
It's important to me to understand the different sub-communities that use Obsidian, so I can help serve their interests.
With the Roundup, it's usually by sharing tools useful to academics, or signal boosting privacy-friendly backup solutions, or collecting resources for our medical users. In Discord and with one-on-one meetings, I often refer people who are overwhelmed to the resources and tools that are most useful for their specific need. Sometimes, I connect business owners to developers & projects that could benefit them. I help them phrase feature requests in a way that demonstrates how the thing they want could be valuable for everyone — and help them see what kinds of features this userbase values most.
I think that work is important, even if it's not always as visible as writing the Roundup.
Note: There are a couple of affiliate links & codes scattered around, but these always come from links I was already recommending and usually I share them because they benefit you too (i.e. getting you extra time on trials).
Check out one of these related posts
An evaluation of the viability of using Obsidian for long form content as opposed to tools like MS Word, Google Docs, & Scrivener.
On the importance of knowing when to sit down and dive deep into your notes... so you don't get overwhelmed always keeping them neat.
Old, simple tools are often still useful, especially when paired with a practice of frequent check-ins with your goals and mental state.