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How to pick a note-taking app, plus Madonnalisa Chan on notes for living & other things worth your attention.
INFORMA(C)TION — February 6, 2022
How to pick a note-taking app, plus Madonnalisa Chan on notes for living & other things worth your attention.

Howdy! Lately, I’ve been thinking a lot about the relationship between digital tools and my ability to focus.

I recently revisited Cal Newport’s Digital Minimalism and am currently re-reading Daniel Levitin’s The Organized Mind. Both have me reconsidering aspects of my personal information environment. But I tend to avoid abrupt changes lest I disturb work in progress. Also, I’m wary of burning cycles on meta-work.

With that in mind, I’d like to share with you how I select one of the key components of my environment: my note-taking app. It’s not something I do often, since it’s a major undertaking. But I’ve done it enough to have a sense of the tradeoffs involved. Given its centrality to effective personal knowledge management, picking a note-taking app is worth doing mindfully.


Digital note-taking next to a Kindle book
Screen capture from my 2013 post about smart sketchbooks.

How to pick a note-taking app

Over the last two and a half decades, I’ve built systems and habits that help me manage information effectively and get a lot done without going crazy. Good notes are central to those systems.

By “good,” I mean notes that allow me to extend my cognitive abilities — i.e., remember things, work through problems, sketch ideas, etc. — without relying solely on wetware. It can happen either on paper or software; what matters is effectively externalizing the thought process. Good notes can also be found when needed, even many years after they were written.

My note-taking system has been primarily digital for many years. I’ve used many apps: Apple Notes, DEVONthink, Drafts, Emacs (org mode), Entourage, Evernote, GoodNotes, Microsoft Word, Notability, Notion, Obsidian, OneNote, Roam Research, SimpleNote, Tinderbox, and Yojimbo. I’ve also kept notes in plain text files in my computer’s filesystem.

I’ve used some of these apps more extensively than others. Some worked better than others — for my needs. Your needs will likely be different. Some apps will be better suited for some use cases than others, but I believe there are general criteria that apply to all of them.

Before I share my criteria, a disclaimer: I’ve mainly used Apple devices over the last two decades. While I’m aware of options for other systems, I don’t have much experience with recent versions of Android, Windows, or Linux. (That said, many of the current choices work across different operating systems.)

With that out of the way, here are my criteria for selecting note-taking apps:

Ease of use

Thoughts are fleeting. Thus, ease of use is an important consideration when selecting a note-taking app. You want your app to get out of the way so it becomes part of your thinking apparatus.

There are two aspects to ease of use: ease of capture and ease of retrieval. Ease of capture has to do with how fast you can take down your thoughts. Ease of retrieval means you can find old notes easily. Ideally, an app will do both, but some will be better at one or the other.

The default Notes app on Apple devices is an example of an app that makes it easy to capture new notes. On iPad Pro devices, tapping the display with the Apple Pencil while the iPad is asleep turns it on and starts a blank note, allowing you to jot your thoughts very fast. That’s much easier and faster than unlocking the device, opening the Notes app, and starting a new note.

Integration

This feature illustrates the convenience of first-party apps. These days, most computing devices come with a built-in application for writing notes. These first-party apps tend to be better integrated with their operating systems than third-party apps.

The tradeoff is that third-party apps offer more (or more specialized) features. Among these is the ability to access your data from various devices, not just those made by a single manufacturer. This brings me to the next criterion…

Universality

Can you access your notes everywhere? Is the app available only on one platform? Can its features be used in devices from different manufacturers? Some apps are more universal than others. Apple Notes works well if you use Apple devices, but it’ll be a poorer experience if you use an Android phone.

Conversely, Microsoft’s OneNote works well on iOS, iPadOS, macOS, Android, and Windows. (It might work well in other platforms; these are just ones I’ve tried it on.) The ideal is being able to access your notes anywhere so that you won’t be locked into one ecosystem.

Portability

It’s one thing to access your notes on different devices, but how easy is it to switch to a different note-taking app? After years of taking notes, you’ll have an archive of valuable data. Can you take it with you if you decide to move?

OneNote and Apple Notes fall flat in this regard; neither makes it easy to migrate to other apps. Both allow you to export individual notes as PDF files, but that’s impractical if you have hundreds or thousands of notes. (The best app I’ve seen in this regard is DEVONthink, which allows you to drag out your data in their original formats.)

Flexibility

What types of notes can you create? Some applications, such as Emacs, only allow for plain-text entry. But others allow a range of formats besides text. Flexible applications will enable you to paste images and photos, scan documents using the phone's camera, write notes by hand, draw, enter math formulas, etc.

Flexibility usually comes at the expense of ease of use since switching modes can be clunky. (Although Emacs is notoriously difficult to learn.) The best app I’ve seen in this regard is OneNote, which allows text, photos, drawings, etc., to coexist seamlessly: you can import a photo, scribble over it, add typed text, etc.

Reliability

To be useful, a note-taking system must be reliable. It helps if you trust that your data will be there when you need it. Few note-taking systems are as reliable as paper and pen. Barring catastrophes such as floods or fires, paper-based notes last a long time. They don’t require recharging and aren’t subject to changing file formats.

With digital notes, there are several considerations when it comes to reliability. One is the location of your data’s “source of truth.” Are your notes hosted in the cloud or are they on your device? The first option provides easier universal access — as long as you’re connected to the internet — while the second is easier to back up.

Locally-hosted notes also insure you against the whims of the market. What happens if your notes are hosted by a small company that gets acquired or (worse!) goes out of business? For cloud-based solutions, I trust large companies like Microsoft and Apple, which are unlikely to go away overnight. But keeping your data on your computer has advantages as well.

Whether you’re hosting notes on your device or in a cloud-based provider, another critical consideration is sync reliability. Some systems work better than others. Your notes should sync between devices seamlessly and quickly; you shouldn’t have to think about this stuff.

Security and privacy

Notes can include sensitive and confidential information. For example, I’ve even seen people who keep their passwords in notes. (Please don’t do this; use a dedicated password manager instead.)

Some note-taking apps offer better security and privacy features than others. Ask yourself: does the app encrypt your notes, either in storage or during sync? Does the provider offer two-factor authentication? Can you lock individual notes or sections of the notebook?

Advanced features

The previous considerations are table stakes. But modern note-taking apps offer powerful capabilities that go well beyond the basics. Here are a few that matter to me:

  • OCR. Many note-taking apps allow you to write notes by hand or scan photos that contain text. Optical character recognition allows you to search these handwritten or scanned notes. This is especially convenient if you have a hybrid paper/digital system.

  • Extensibility. Some apps can be extended by third-party developers, greatly expanding their feature set. For example, Emacs and Obsidian both have very active communities of developers developing plugins, modes, and more; they are as much platforms as applications.

  • Hyperlinking. Some apps allow you to reference other notes by linking to them. How easy/seamless is the linking process? Many apps allow wikilinks, which enable you to create new notes and links to existing notes while you type, without taking your hands off the keyboard.

  • Backlinks. Whereas hyperlinks and wikilinks have been around for a while, backlinks are a newer feature. While “regular” links allow you to jump to other notes from the note you're currently in, backlinks show you all incoming links — i.e., notes linked to the one you're currently on. This is a convenient way of discovering relationships between notes.

  • Bottom-up structure. Backlinks, wikilinks, and tags allow you to capture notes without worrying about where they should be stored. Conversely, some apps impose a top-down structure. For example, OneNote encourages you to organize your notes into individual notebooks divided into sections. Compare this with Roam Research, which doesn't enforce a hierarchical structure. Instead, you type into “day notes” that spawn other notes as thoughts occur to you. This approach encourages a more bottom-up approach to note-taking.

  • Artificial intelligence. Although not yet common, advances in AI make it possible to organize and find data in your archive more easily. DEVONthink stands out in this regard: I use its AI engine to manage my notes and help me discover relationships between whatever I’m focused on and older notes in my archive.

Cost

I’ve left cost for last because it matters least to me. Note-taking is one of the reasons I use computers, so I’m willing to pay for quality applications that meet my needs. That said, cost is a crucial consideration for many people.

Built-in applications such as Apple Notes are free in the sense that they come bundled with your device. Some apps, such as Emacs, are open source and can be downloaded for free. But even paid apps tend to be relatively inexpensive.

Many have moved to a subscription model. While this may seem inconvenient, I like knowing that companies providing these essential services have a viable business. I’d rather avoid switching apps, and yearly or monthly revenue is a more sustainable model for providers — especially now that syncing (which has recurring costs) has become essential.

A final consideration regarding cost: don’t just think about price, but about the time it’s going to take you to learn, migrate to, and master the app. Some apps might be cheap or free, but can be hard to learn or difficult to integrate with your workflows. For example, Emacs’s org mode is free and powerful, but it takes time and effort. This, too, has a cost.

Which is right for you?

As you’ve seen, there are many factors to consider when selecting a note-taking app. There are also many options.

The best app for you depends on your needs. If you mainly capture throwaway notes (e.g., grocery lists), you don’t need to worry about your data’s longevity. But if you teach a university course (as I do), your archive will matter a lot. Professionals might be somewhere in-between. So, start with your needs — but consider that your needs might change over time.

My note-taking system is continually evolving, which is why I opt for applications that offer a mix of extensibility, openness, and capabilities. But this comes at the expense of money and reduced convenience. It’s a tradeoff I’m willing to make, but I’ve made it consciously. Hopefully, this list helps you do the same.

What about you? Why did you pick your note-taking app? Are you satisfied with it, or are you looking to change? Please let me know if there are essential criteria that I missed.



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Upcoming workshops

Building a Personal Knowledge Garden
April 18, 2022 — IA Conference (online)

Strategic Information Architecture
May 24, 2022 — UXLx (Lisbon)

From my blog

Things I was wrong about: 280 characters
First post in a new series wherein I reconsider my positions. So much to be wrong about!

Room to think
Highlighting an intriguing commercial (yet free) offering designed to help you reclaim your attention. It’s surprisingly effective.

Clearer Gmail navigation
An upcoming change to Gmail’s UI will clarify the system's conceptual structure.

Live-tweeting The Organized Mind 
As I mentioned above, I’m re-reading Daniel Levitin’s The Organized Mind. I’m tweeting my notes as I go through the book, and I’d love it if you could follow along and comment. Something like an open public book club?

Also worth your attention

Domain modeling
Andy Fitzgerald: “By uncovering the assumptions and tacit rules that plague your content ecosystem, domain modeling can help you facilitate the shared vision necessary to create resilient, scalable systems for communication across channels.” 👏👏👏

Trusted agitators
Laura Yarrow: “Over the years the most common designer complaint has always been ‘No one listens’ and ‘UX isn't a priority/understood’, so I want to throw something controversial out there: Some of this is our doing.” Good Twitter thread on the role of design.

Tesla design
Scott Jenson on why automotive design is hard: “It’s the context and the severe consequences that make it far more impactful than a poorly designed phone app.” (The issues he raises also apply to other fields.)

Cal Newport interview
Deep Work and Digital Minimalism helped me become more mindful in my work and my relationship with technology. This conversation on the Tim Ferriss podcast offers insights into Newport’s approach and practices.

Eno on scenius
YouTube video of Brian Eno describing his concept of scenius. The visuals aren’t very polished, but the concept is an important contribution to how we understand creativity and this short video is a good intro. (H/t The Long Now Foundation) 💡

Stewart Brand interview
“There's lots of stuff that obviously is the wrong information, but I think agency has gone up, and victimhood, which is the opposite, has gone down.” Among other things, Brand covers things he’d do differently if he were writing How Buildings Learn today — including changes to the classic pace layer diagram. 🏠🌎

The Informed Life with Madonnalisa Chan

Episode 80 of The Informed Life podcast features a conversation with Madonnalisa Chan. Lisa is director of product management, taxonomy, and content services at Salesforce. I’ve known her for a long time and admire her work as a taxonomist, but this conversation doesn’t focus on her work. Instead, we discuss how she uses physical notes to manage her personal life.


The Informed Life episode 80: Madonnalisa Chan

Parting thought

The idea that information can be stored in a changing world without an overwhelming depreciation in its value is false.

— Norbert Wiener (1950)

Thanks for reading! 🙏
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