Obsidian, the note-taker of my dreams

The backstory

(Hate navel-gazing backstories? Just want the practical details? Feel free to skip to how I’m using Obsidian!)

I’m one of those people who are always trying new systems, convinced that “all I need” to finally be on top of things is in the next system. Occasionally it’s even true, but usually takes a whole lot of trial, error, and customization.

I’ve sought and tried systems for everything, big and small: recipe organization, the best way to hang damp bath towels, space-saving in my tight kitchen cabinets, reading lists, storing my craft-store–worthy collection of embroidery thread… You name it, I’ve probably tried a system for it.

The two lingering “itches” that were still niggling me: task management and knowledge management.

Task management is an incredibly common challenge. There are mountains of books written about it (I’ve read a lot of them), planners that promise help based on the way you think, the timescale you prefer, or the latest research (or all three), strategies for making the process easier or better, and software for pretty much all of the above.

I’ve tried dozens of approaches and gotten something valuable from most of them, but still hadn’t found a system that was flexible and low-friction enough for my ADHD brain to love.

Knowledge management isn’t as well known. It usually comes up in a work context, to handle the challenge of making tribal knowledge explicit so it’s not siloed or dependent on key staff staying forever. I’d written up “Standard Operating Procedures” when I ran my own company years ago and still reference the content to this day.

The “itch” I felt was around books and ideas: I read many, many good books. I also have a so-so memory (unless you’re talking about lyrics of songs I haven’t heard for 10+ years—then it’s stellar!). It was frustrating that I’d spend so much time exposing myself to good ideas, only to remember just one vague concept—if I was lucky! I wanted a way to save the best ideas I encountered in a way that would also resurface them from time to time, ideally at just the right time.

I didn’t know the term for it at the time, but it turns out what I was looking for was “Personal Knowledge Management” (PKM for short). I took a meandering path to get there (book summaries, which led me to commonplace books, which led me to Zettelkasten, which led me to the concept of Building a Second Brain).

When I stumbled into the Second Brain Summit, I immediation realized this concept was what I’d been looking for. It still took some time and experimenting with different systems; I started out with August Bradley’s excellent Pillars, Pipelines, and Vaults in Notion, and that helped me discover what did and didn’t work well for me.

When I first came across Obsidian, I’d initially been turned off by its text-based everything. I thought the double brackets were ugly. But after using Notion for a while, I realized that what I really wanted was fewer decisions when adding content—about where to put it, how to organize it, and how to format it.

I finally gave Obsidian a fair shake, and as you’ll have intuited, it’s the solution I’ve been looking for.

What I like about Obsidian

Note that these are my preferences; I’m specifically calling them out because you may have different preferences that mean that Obsidian would be frustrating to you.

  • It’s customizable. By default, it’s pretty bare-bones, but there are hundreds of plugins that help with everything from formatting to complex database-type functions. For a developer like me, there’s also the possibility of writing my own plugins to further customize the behavior.
  • It’s designed for connecting content. Almost all similar tools will let you link content, but Obsidian is built around the idea as a core philosophy. Whenever you’re looking at a note, there’s a (hideable) sidebar that shows you what other notes this note links to, and what other notes link to this one. Add to that a visual “network graph” and there’s tremendous potential to “follow a thread” of ideas.
  • It’s limited but powerful in its formatting. My most-used formatting (headings, bold, italics, bullet points) are easy to and intuitive to add. Formatting is tied to function: headings and bullet points indicate hierarchy and have a little toggle to hide or show the content, which makes it very easy to skim even very long or complex content.
  • It’s future-proof. Because it’s based on a simple folders-and-text-files structure, there’s no foreseeable future in which my valuable-to-me content will become unavailable to me. It’s stored on my computer, backed up with my regular backups, and will be readable even if the Obsidian software ceases to exist.

How I’m using Obsidian

Obsidian works with a simple folders-and-files structure, and is tremendously customizable via plugins.

My Obsidian file structure is buit around my specific needs and preferences in a few ways:

  • Almost all of my notes are stored in the main folder. I played with creating sub-folders to group things, but found trying to decide where something “belonged” introduced unhelpful decision-making and friction. Because the search and tagging systems work so well, there’s no benefit (to me) in having each note in a sub-folder. (It took some getting used to, though.) There are a few exceptions for practical reasons, mentioned in the next bullet points.
  • Notes directly related to my job are stored in a sub-folder I named “Work & Clients”. This makes it easy to group tasks (discussed later) into “Work” and “Personal” categories, which is helpful in maintaining a healthy separation between work and not-work time. It is also easy to determine if a note should be in the sub-folder or not, so it doesn’t suffer from the decision-fatigue I experienced when I had lots of sub-folders.
  • There are groups of notes that serve a more utility purpose or have a clearly-defined function, and I put those in sub-folders. Specifically:
    • Templates are used to prefill a note with default content, but aren’t meaningful notes in their own right. They go in my “Templates” sub-folder.
    • My “Daily Notes” sub-folder holds notes that are auto-generated each day through a combination of a plugin and a template. These notes help me organize my tasks for the day and do daily habits, but don’t necessarily benefit from resurfacing.
    • I’m trying to get in the habit of doing regular reviews (weekly, quarterly, and annually), and those go in a “Reviews & Planning” sub-folder. They also rely on templates for their initial structure.
    • I keep all of my attached media (images, PDFs, etc.) in an “Attachments” sub-folder for simplicity.

Using Obsidian Tasks

For the task management part of my needs, the Obsidian Tasks plugin has been incredibly useful.

I was introduced to the plugin through Jenny Liang’s blog post on the topic, and have used her setup as inspiration.

I create tasks anywhere and everywhere they are relevant. I have a note for each of the clients at my work, and put tasks related to their projects in those notes. I have generic work notes like “Meetings” and “Admin” that provide a place for routine tasks not tied to a specific client. I have notes for people like my husband and son, and put relevant tasks (like a recurring Thursday task for “Take the kid to his viola lesson”) there. I have a “Productivity” note that houses my recurring tasks for daily check-ins and planned improvements. I have notes for all of my personal projects and add tasks there as needed.

The great thing about all of these topical notes is that they don’t only contain tasks. They mostly contain other information, like plans for projects, call notes, estimates, anything I might want to refer back to in the future. But the Obsidian Tasks plugin uses a specific (customizable) format and so it can recognize anything, anywhere, that uses that format.

It did take a little while to get my various topic notes set up, but now it’s rare that I want one that doesn’t exist already—and if I do, it takes mere seconds to set it up.

Where Jenny Liang has an “Action Zone” (this comes from the Pillars, Pipelines, and Vaults system mentioned earlier), I set up something similar in my Daily Notes and a standalone “Tasks” note.

My Daily Note template pulls in any tasks in any note that have a due date of the current date (or before 😬) and groups them by “Work” (if they came from notes in the “Work & Clients” sub-folder) and “Personal” (from any other notes).

My “Tasks” note has a broader overview, featuring all my tasks broken down into useful categories, like “Tasks that aren’t scheduled yet” and “Working ahead” (tasks that aren’t due yet but can be started) as well as standard ones like “Today” and “Overdue”.

One of my favorite things about Obsidian Tasks is that it is agnostic about the content of a task. Want to put a time at the beginning of the task text, so it can be sorted in order? Go for it. Want to remember the context of a task by linking to a Slack message, web page, and/or the company-mandated task? No problem.

The ease of adding tasks (particularly once I got used to the keyboard shortcuts) has made it such a habit that it’s unexpectedly reduced the number of browser tabs I keep open and the number of times I go down a rabbit hole each day. The fact that it’s so trivial to add a task combined with the confidence I have that I’ll be able to easily find it when I want it (better still, that it will automatically resurface at an appropriate time) means I don’t have to keep everything close at hand when I’m not sure what to do with it.

Update: I recorded an off-the-cuff video showing how to set up Obsidian Tasks.

Obsidian and a Zettelkasten approach to personal knowledge management

Without getting too keep into the weeds of Zettelkasten, the core piece I’m embracing is linking. (Nick Milo has built an entire brand around this called “Linking Your Thinking”.)

The main way this plays out is simply that I add notes with abandon, but try to link them to other relevant notes. I’m still in my early days with Obsidian, but I’m already finding myself making and rediscovering connections between ideas that enrich my thinking.

It also gives me a reason to actually note down my thoughts, particularly when an idea jumps out at me while reading or listening to a podcast. Instead of just thinking, “Hmmm, that’s interesting” and moving on, I’ve found that writing it down often spurs deeper thought and I’m more likely to notice complementary or opposing ideas afterward and let them have their say alongside the first note.

Being intentionally loose about any kind of official structure means the content is the first priority, linking is second, and that’s really it. Not having to worry about where to put it or how to organize notes means that even brief or simple thoughts get recorded and become part of my larger body of knowledge.

What about you?

If you’ve made it all the way to this point, you deserve a medal. I hope this has been helpful, and I’d love to add more (maybe some pictures!) to make it more helpful, either by better organizing this post or by adding new ones that address specific questions. So if you have questions or feedback, I’d love to hear them!

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