Practically Paperless with Obsidian, Episode 18: How I Organize My Notes

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During the years that I was Evernote’s paperless ambassador, one thing I learned was that organization was a very personal thing. This came as no surprise. Each person is unique, has unique requirements, and the result is a unique was of organizing their notes. What was a bit surprising at the time was how vocal people were about what method of organization was best. I’m not doing that here.

Recently I wrote about what I think of as “how-to versus how-I.” My migration from Evernote to Obsidian is an experiment. My use of plain text files for the bulk of my output is an experiment. Some things work, and I keep those things around. Other things don’t work and I toss them or try to find ways to improve them. So when I talk about how I organize my notes in Obsidian, I am talking about an experiment that I am working on that meets my own unique requirements. What works works for me, and may not work for anyone else. But I think it is good to have examples of what people are doing because there is always the possibility to learn something.


Lessons from Evernote

Consider some lessons I took from how I organized my notes in Evernote:

  1. The organization grew organically without much initial thought.
  2. I considered notebooks topical and that all notes related to the topic should go into the notebook.
  3. I thought of tags as themes: a mechanism that allowed me to span or collect topics together.

This resulted in an overly complicated set of notebooks, where it was sometimes difficult to find something because topically, I put it into one notebook when, thematically, I looked for it elsewhere.

Lessons from Obsidian

I have been using Obsidian for over a year now, and in that time, I’ve experimented quiet a bit. One thing that I have found, is that my notes fall into several general categories:

  1. Attachments: PDFs, images files and other files stored in my vault that are generally not plain text. Example: a PDF of a W-2
  2. Documents: Documents are attachments with context. They are wrappers for the attchments. That is, a note in which I transclude an attachment file, in order to provide additional meta-data and context to that file either through YAML frontmatter, note text, or links. Example: a note that transcludes a PDF of W-2 and also contains meta-data (tags, etc.) about the document, as well as any other remarks or links that I add. For more on how I think about document notes, see Episode 1.
  3. Permanent notes: I am borrowing this term from Luhan’s Zettelkasten methodology. Permanent notes are notes about one thought that can stand on its own, written in my own words, with context added in the form of links and tags. Example: a note about how power differs in the Senate and executive branch, based on reading I have done.
  4. Maps of Content: Notes that pull together links to other notes in a unified context that allows for easy access to relavant information. Example: a note about a specific vehicle, that links to other notes and documents related to the vehicle, and provides additional context in the form of a timeline or backlinks.
  5. Writing: Notes that contain writing: stories, letters, blog posts drafts, essays, etc. Example: The note containing the draft of this blog post.

Looking through the notes in my vault, I can generally put each one into one of these buckets. There are some exceptions, of course, like templates or my daily notes file. But the vast majority fit into this framework.

As I was thinking about my requirements for organizaing my notes, I tried to keep all of these lessons in mind.

My Requirements

Since the basis of organization stems from one’s requirements, let me talk about the requirements I had in mind when I was organizing my notes in Obsidian. As I thought about how I might better organize my notes in Obsidian, two requirements began to emerge:

  1. Optimize for finding things later as opposed to organizing them now. This is something I have emphasized in previous episodes. It takes time to maintain a taxonomy for notes. The important thing for me is not so much how the notes are organized, but how quickly I can find them when I need them.
  2. Remember that I may not be the only one that needs to access these notes and plan accordingly. Kelly may need access to the notes and she needs to be able to find what she is looking for. We jokingly call this “succession planning” but in reality, if something happened to me, access to my notes, which contain all kinds of information that she would need, would be vital. Finding that information quickly would take some burden off her mind.

(Re)organizing My Vault

These two requirements led to some decisions that I made about how I’d structure my vault.

  1. Attachements, documents and permanents notes can have a completely flat structure. I typically access these note in one of two ways: via an MOC note, or via a link on another note. It is rare for me to search for these notes directly. The allows for a flat structure.
  2. Maps of content (MOCs) need to be very easy to find. Because they are topical and provide sturcture and context, they lend themselves to a more hierarchical structure. MOCs are also the most useful mechanism for Kelly to find what she is looking for.
  3. Writing notes could go into their own folder and be organized in a relatively simple hierarchy, the way I might organize them on a file system.

I went about making these changes. It was not hard to do because Obsidian handles all of the linking and indexing behind the scenes as notes move around. I was tempted to have just four or five top level folders, so that my vault would look something like:

  • attachments
  • documents
  • slipbox
  • writing
  • MOCs

But I decided for ease-of-use to keep to a flatter hierarchy and implement the taxonomy through a different mechanism. At the top level, therefore, my vault looks like this:

The vast majority of my note can be found in the attachments, document, and slipbox folders. I’d guess they contain 90%+ of all of my notes. The structure for MOCs is flat, too, but contains some structure to make it easy to find the MOC I’m looking for. Still, the MOCs make up a small fraction of all the notes, even though they link to many of them.

Some examples I used to test this structure

Example 1: Tax season – MOCs to the rescue

As I write this, I am preparing to send all of our tax information to our accountant for preparation and filing. An MOC for all tax-related documents makes this a simple exercise. As tax documents come in, I add the PDFs to my vault as attachments, create document notes for them to capture context and meta-data, and then add a reference to the document on the MOC note for taxes.

Here is what the “Tax Documents” MOC looks like (with some annotations in red):

In the Tax Documents section, there is a corresponding year for each year in the Tax Returns section and under each section is a list of all of the tax documents for that year, each of which in turn transcludes the PDF attachment as well as meta-data for the yearly summary table.

I’ve tried to make this a one-stop-shopping document for anything tax related. It is useful for more than just tax season. We recently refinanced our house (squeezing it in before the rates started to go up again) and needed to provide some tax documents as part of that process. This made it easy. If Kelly needs some tax information, she know to go to this note, and it will point her to everywhere else she needs to go.

When I go to sent the documents to our accountant, I’ve already got everything in one place. It’s just a matter of uploading the documents to their secure portal.

This MOC meets both by requirements: (1) optimizing for finding things later, and (2) making sure Kelly can find them too.

Example 2: Managing services – herding kittens

I miss the old days when you had your phone bill, you gas bill, and electric bill, and maybe a newspaper subscription to keep track of. Today, everything is a service: from streaming media to software to digital subscriptions, there are tons of services that need to be managed and coralled.

Within my MOC structure, I have folder called “Services” and within that folder is an MOC note for each and every service we subscribe to. Combining the usual utilities with subscriptions and software services, it is a long list. Each service is billed in its own way, on its own cycle. Each costs something different. It can be hard to stay on top of. I do it through MOCs using a simple set of guidelines:

  1. Each service gets its own note.
  2. Each note has a specific set of YAML frontmatter at the top to keep track of the basics. I’ll come back to this in a moment. Currently, it looks like this:
  1. The note itself has two main sections: (1) Service info, which includes things like where the service is billed to, links to managing the account, how to cancel the service, etc. (2) Service notes: if I have to contact support, the notes related to the contact go in this section. The dates are links back to the daily note on the date of the contact. Here’s an example:
  1. With a note for each service populated with the meta-data, I have a Service Summary MOC note. This note uses the Dataview to summarize all of our “active” services with links to the service note, and listing the monthly and annual costs, and the due date of each. This allows us to view, at-a-glance, all of the services we have, how much they are costing us, and when they are do. If we cancel a service, I mark it’s meta-data status as “canceled” and it drops off our active list. Here is a snippet from that summary note:

This model has worked very well for keeping up with all of our services. The summary note makes it easy to find anything we are looking for. The MOC note for each service contains everything we need to know about that service and its history. There only one place we need to go to look for the information so it is easy to find.

Example 3: Continuity planning – a step-by-step guide

Back when I was Evernote’s paperless ambassador, one of the more popular pieces I wrote was one I called 6 Steps for Life Continuity Planning in Evernote. In our house, we jokingly call this “succession planning” to take away some of the discomfort of thinking about this kind of thing. As part of my migration from Evernote, I’ve been working on using the features of Obsidian to improve upon how we document this continuity planning. An MOC I call “Succession Plan” plays a central role in this.

The Succession Plan MOC centralizes everything that Kelly or I would need if something happened to one of us. It is also written so that if something happened to both of us, the folks who would be responsible for our affairs would have a detailed roadmap.

The document is broken into two parts:

  1. A step-by-step guide for everything that needs to happen, in a logical order, with links to all of the relevant documents, contacts, phone numbers, email addresses, etc. It is all right there in one place. Go to that note and you have everything you need at your fingertips.
  2. A kind of annotated index to my Obsidian vault, with links, so that if there is something that is needed that is not in the step-by-step section, there is a framework for locating it in the index section.

I try to keep this up-to-date, and it is still a work-in-progress, but there is enough there that it would be useful in the unlikely event of a water landing. Here is a high-level glance at the structure:

Once again, I’m focusing on finding things later when they are needed as opposed to a deep hierarchical structure to how the notes are organized.


Like any organizational structure, this is a work-in-progress. It evolves as I test things out, figure out what works and what doesn’t, and make adjustments. But this is the closest I’ve come to accomplishing an organization that doesn’t require me to constantly think about where I need to put something, and instead focus on linking to it in ways that will be easy to locate later on. It is an easy system to work with and so far, it is working well for me.

In next week’s post, I’ll talk about archiving notes.

Prev: Episode 17: Six Ways I Use Note Links
Next: Episode 19: Archiving Notes

Written on February 2-13 , 2022.

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  1. Love the series! This episode raised a couple of questions:

    You mentioned here sharing notes with Kelly. What’s your sharing setup, and how two-sided is the collaboration? Is Kelly onboard with reading and writing plain text Markdown files using her own copy of Obsidian? Constructing search incantations? That seems like a hard sell for non-techy/nerdy partners (maybe Kelly is techy/nerdy 🙂 )
    The succession planning note is fascinating to me! Would you consider dedicating a post to this one? 🙂 Maybe an update of the Evernote variant.. How does a third person (after Kelly and yourself) gain access to the note (and the entire vault) if shit hits the fan? How would they know to start with that specific note? How granular and specific are the instructions left there? How would they access additional accounts – do you keep passwords in Obsidian? Or a separate emergency contact setup in a password manager? What about 2FA-protected accounts?

    Sorry, I cheated, I baked in a bunch questions into “a couple” 😉

    1. Itamar, thanks for the kind words on the series! Access for Kelly is simpler than you might think, thanks to MOCs: The short version is based on 3 notes:

      1. A note that she keeps in her own Apple Notes with instructions for how to access Obsidian on my computer (she already has access to my computer if she needs it).
      2. An index note in Obsidian that provides some context and links to just about anything she might need. For instance, there is section for “Important documents” with links to the documents. There’s a section for “Instruction manuals”, “Services”, etc. All she has to be able to do is open Obsidian on my computer and then go to that note. From there, she can click on links to get what she needs, no need for searching.
      3. The “Succession Planning” note that I referred to, from which she can get access to any relevant note or document she needs.

      I have tentatively scheduled a post on sharing notes in Obsidian that will cover these topics in Episode 23 (approximately March 22).

      For your question about third person access if something really bad happens: a printed copy of that first note that Kelly has in Apple Notes is on file with our lawyer, along with other important papers like wills, etc. They know who should be given access to that information. That seemed the most reasonable way to keep things simple and secure.

  2. This post was very useful. As I am trying to figure out how to use Obsidian, I agree with so many points that you included in your discussion. I plan to transfer my notes from Evernote to Obsidian. Thus, thinking how I want to organize my thoughts, notes, attachments, etc… remains the main reason why I haven’t completed the transfer.

  3. Hello! Thanks so much for this series. I think I’ve read the posts through four times now and I keep learning.

    I’m curious about your flat folders (specifically “attachments”) a year or so into this process is it still working for you? Does Obsidian bog down as the number of files that aren’t notes grows within the vault? Is your setup starting to feel ‘heavy’ at all?

    I’m re-working my file system (about the only benefit of an operating system crash!) and was planning on keeping my writing in Obsidian and ‘everything else’ outside of it. But this idea of wrapping attachments with an Obsidian note, and then building MOC’s for navigation is compelling. I’m power of attorney for my father and I’m getting a ton of documents emailed to me from his care home, etc. Being able to add context to each document and collecting them into an MOC seems like a lot of work, but also worth the effort.

    One more Q: do you stage your attachments somewhere until you build a note for them?

    1. Mark, my folder structure has come a long way in the last year. Probably so much so that it is worth writing an entirely new post about at some point. A few things I will note:

      1. Most actual attachments (PDFs, images, etc.) still go into a single “attachments” folder. It doesn’t feel that heavy, but then again, as I write this there are only about 600 files in that folder.

      2. I’ve moved more and more toward using Obsidian as the “index to my life”, but not so much for regular “notes” like reading notes. I had a kind of epiphany a few months ago that the best note organization strategy for me turns out to be the one I used in college. Handwritten notes on loose-leaf notebook paper that I can put into 3-ring binders and shift around as needed. Obsidian is an index to everything, but the stuff I keep in it is now similar to what I used to keep in Evernote: archives of old papers, documents, tax forms, etc. all nicely index via daily notes and other MOCs.

      3. To answer your question about staging attachments: like I said, they all go into the Attachments folder, and I usually build a note for them at the same time. If I don’t, I’ll forgot and won’t get around to it. I have limited what I make wrapper notes for, however, to only those things where it proves absolutely useful. Otherwise, I’ll just link directly to the attachment (PDF, etc.). Examples of what prove useful are document that relate to someone in the family; and letters I write or receive. These all get wrapper notes and linked to the “Person” note for the person to whom they are related. I keep the Backlinks view in my notes turned on so that if I am looking at, say, my son’s note, I can easily see all of the documents I’ve linked to him.


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