Note-taking that scales

Intro

The digital era, with all of its positive influence on humanity, such as the abundance of knowledge, is also characterized by an enormous amount of information that we want and need to process. Books, articles, posts, feeds, videos, online meetings, chats, etc. Sparking ideas, memorable quotes, funny memes, important tasks, plans and dreams, decisions and action steps, and the list goes on and on.

Moreover, in your casual life you are usually controlling this information flow (well, mostly), but at work — not so much. Because other people depend on you, because they throw information at you and force you to process it, or maybe because of your higher ambitions.

As a CTO, I deal with an enormous flood of information every week. My direct team surpasses 30 people, with a dozen backlogs and lots of stuff happening at the same time. According to my “Vimcal Rewind", I had more than 1000 meetings this year — and every meeting is a waste of time if it does not have any notes, decisions, answers, or action points attached to it.

Obviously, the human brain was not created to handle that amount of information, at least not by itself. Luckily, God made people to be intelligent tool builders. We build tools that give us superpowers and make us able to do what we weren’t able to do naturally. We’re building bicycles for our minds, as in the famous quote of Steve Jobs.

The evolution of the (second) brain

Notes

The most obvious solution for a human brain when it cannot hold a certain amount of information is externalizing — organizing that information on an external storage, your “second brain”, e.g. a note-taking app.

I remember starting my note-taking journey in Google Keep years ago. There is a default app called Stickies on macOS with even more simplistic capabilities. Raycast Notes introduced in 2024 as a "new old feature" of the somewhat overhyped Raycast app is another example of this approach.
Some people simplify this even more for themselves by storing their notes as plain text files on their desktop.

It's probably the simplest form of note-taking… It does not scale well, though. When you have a couple of dozens of such notes, you might still be OK. But what happens at scale?

Folders (or notebooks)

How would you feel if you found a pile of 100+ notes scattered all over your work desk? It would probably feel overwhelming and counterproductive to find the right note in that pile.

What do you do when you sense that there's too much on your plate? You organize. The most basic form of organization, borrowed from the paper age, are folders.

This is the most typical organizational feature that is available in Apple Notes, Microsoft OneNote, Standard Notes and many other apps for years and years.

You will consistently see one important thesis throughout this blog: apps and features matter less than methodology. It does not matter what features some app or system provides — if you don’t have a methodological approach, your system will become unusable eventually.

So, for your folder-based notes app to survive in the long term, you’ll need to choose and consistently follow one of the folder-based organization methods. I’m going to dive deeper into some of them in a separate article.

Tags (or labels)

Any folder-based system has one critical flaw: the information that we need to process every day is mostly not hierarchical. It’s often challenging to categorize. To tackle this friction, it is typical to use tags (depending on the app, they could also be called labels, hashtags, or mentions).

The basic idea of tags is to allow you to mark various pieces of information across your system, and be able to retrieve everything marked with a specific tag easily, regardless of where it is located.

The obvious benefit of tags over folders is that one piece of information can have multiple tags. So you no longer spend time deciding which folder should this note belong to — you trust your intuition and mark your note with all the tags you think might be relevant. And you can be sure that you’ll find that piece of information when you look into any of those tags.

The vast majority of modern note-taking apps support tags in one form or another.
macOS has tags even on the operating system level, allowing you to mark files across different folders of your file system.

I will elaborate more on the systems and approaches to tagging in another article.

Folders and tags — simplified

To paraphrase Spider-Man, "with great power comes great pain in you-know-where". Now that you introduced tags, you need to maintain two systems at once: figure out what folder to put your note in, and figure out the tags that you should put in that note, for you to be able to find it later.

Hello Apple Notes, hi Obsidian, and several other note-taking apps.
Some of them, like NotePlan and Agenda, complicate things even more by distinguishing hashtags from mentions, essentially giving you three systems to maintain instead of two.

To make it somewhat easier for you, some apps (like Bear or Drafts, for example) eliminate folders altogether and focus solely on tags. These apps understand that there’s going to be far too many tags in your system, so they allow you to make those tags nested (kind of imitating folder structure, but with the flexibility of being able to find your note in multiple places at once).

Other apps (like Capacities) simplify folders for you instead: they promote using only one level of hierarchy, and define that single level in such a way that it’s obvious to which folder your note should belong. The most intuitive is organization by object type: what object does this note describe? Is it a person, a place, a meeting, a project, an idea? This way, they provide you with enough simplicity and flexibility to organize your content by a combination of "object type + tag".

Observation: if we're talking about Capacities specifically, this approach of "object type + tag" did not scale well either. So, over time, they introduced collections of objects and tags (relatively alike to a second level of hierarchy).

Backlinks revolution

Even with folders and tags, there are cases when it’s still quite difficult to track the connections between your notes.

• Every so often you notice that in some longer notes it’s not enough to just know that these two are somehow connected. You need to understand the exact context of that connection.
• Other times you would rather not mention a whole tag at some place of a note (because not everything under that tag relates), rather you would like to mention a specific note.

This is when you suddenly realize: “My digital notes are like Wikipedia. My notes are like webpages on the Internet. Why don’t I just add a link to that note into this note?” And you start interlinking individual notes.

Even the basic note-taking apps like Apple Notes have already introduced the capability to mention one note in another note, thereby creating a clickable link between the two. Nowadays, if a note-taking app does not support note interlinkage, it can be considered obsolete.

But then you realize that if you went from note A to note B, there is a great chance you’re going to need to go from note B to note A at some point. You may start bi-directionally linking your notes, of course, but this quickly becomes cumbersome and challenging to maintain consistently.

Here, another bicycle for your mind comes into play: the backlinks. Modern note-taking apps usually provide a dedicated area to show you every note that has a link to your current note, so you no longer need to insert those bidirectional links to know where this note was ever mentioned. Whew, did a mountain just fell off out of your shoulders, too?

Thank you, NotePlan, Reflect, Capacities, Craft and others, you saved our lives!
Some apps go even further and provide the ability to visualize those connections between your notes. Thank you Obsidian for the inspiration. Thank you Capacities for almost perfect implementation.

Backlinks implementation is quite diverse when you compare the apps I’ve briefly mentioned above, and so are the workflows that these apps propose. I will dive deeper into this topic in another article.

Paradigm shift that changes everything

Now, what if I told you that the way you started to take your notes was not the best way in the first place?

What if scaling from a single pile of notes to multiple folders, then to nested folders, then adding tags on top, then adding links and backlinks — all that was meant for you to have an enlightenment, and bring you to simplicity instead of complexity? Let's turn those stages of evolution upside down!

As I have already mentioned, I am constantly dealing with a huge amount of information because of my job as a CTO. Over the years, I’ve tried various approaches and tools for note-taking, and all of them crumbled as soon as the number of notes reaches a certain amount (which happens inevitably at some point).

The main organizational principle that helped my system not to become cluttered and crash or overwhelm me over time was to rely on the backlinks more than on the notes themselves. Allow me to explain what I mean.

1. Instead of choosing a folder where to put your note or choosing the tags for your note, or even creating a file for your note, you just start writing. The most obvious place to start writing is your daily note — one note marked with today's date (that is usually created automatically for you by apps like Reflect, Capacities, NotePlan or Craft or others).
2. You write your notes in a bullet journal style. Don't get overwhelmed, this just means that you write like you normally do, but start every paragraph with a bullet or dash, so it becomes a list. And instead of using headings for structuring, you just make your list nested.
3. When you encounter anything worth mentioning in your note, you wrap it in [[ and ]] which means creating a wiki-link in the majority of note-taking apps. Essentially, this way you backlink your information: now when you open that back-linked piece of information, you can see all the daily notes where it was mentioned in your backlink area.

So, as a result, your library of notes now consists of two pieces:

1. Daily notes, where all the actual content is written.
2. Regular notes, back-linked from the daily notes. A lot of these notes could even be empty, and serve just as a starting point to find everything relevant to that particular subject / object / topic from your daily notes.

Disclaimer: I originally learned that concept from the Reflect app that actively promotes exactly this approach to note-taking. But of course, they were not the first who invented it. They just managed to create a good tool that provides everything you need for this approach to work comfortably.

This approach, as simple as it might look like, provides enormous benefits to your note-taking experience, especially at scale, when you accumulate plenty of notes:

• When you're taking your notes, you spend zero time and mental effort on organization. You don't choose folder or tags, you just write. And you quite naturally mention other people, meeting series, projects, places etc. It’s such a natural flow you’d be amazed how quickly you get used to it.
• When you need to find anything related to a specific person, project, topic or etc. you just look at its backlinks area.
• As your note-taking happens in daily notes, your content naturally grows old over time, so the back-linked content will start with the most relevant notes and as you scroll the backlinks area you see older content.
• No matter how many notes you take, you are not overwhelmed by them because they stay out of your sight until you actually need them, hidden in the daily notes. You will have a magnitude less regular notes using this approach than you would have otherwise, so navigation becomes easier.

Two additional organizational features that good apps (like Capacities or Reflect) usually provide to make this workflow complete:

1. Setting type for your regular notes. As already mentioned above, in Capacities you set your object type explicitly. In Reflect they keep it simple: you just add a single hashtag that marks object type. This helps you to filter your regular notes in case you have too many of them over time (or in case it just makes sense to you to categorize them).
2. Pinning your regular notes. Typically, you have a handful of notes that you do want to keep at your sight, your primary focus or starting point. Things like your most important projects for this week, or goals for this year, or a note for the quotes from the book that you’re reading, or other content that you come back to frequently. These apps allow you to pin that content to your left sidebar for easy access.

And this is it! A simple and natural approach that relies more on backlinks than on tags or folders, and provides you a clear starting point to start writing and an easy way to resurface the content you need without overwhelming you with complexity.

This paradigm shift reduced friction when taking notes, proved to be efficient to find any piece of information I require at any point, decreased stress and overwhelm, and brought more joy into my “personal knowledge management world”.

I hope it will help you in a similar (or some other unique) way, dear reader. That's everything I wanted to share with you today.

Thank you for reading, and until the next time!