Re-thinking Digital Note-taking

Note-taking is central to my work. Every day I sketch ideas, capture meeting minutes, annotate bookmarks, draft new posts, etc. I’ve done this for a long time using both digital and analog notebooks. However, over the last couple of years, I’ve started feeling constrained by some of my tools. In particular, I’ve realized that I can create the most value when I can quickly spot patterns to generate insights, but the way I’ve been taking notes doesn’t lend itself to sparking new connections.

My primary note-taking tool over the last eight years has been OneNote. I started using OneNote because I wanted to hand-write my notes digitally, and Windows tablets were the only viable way to do so before the Apple Pencil came along. When the iPad Pro + Apple Pencil appeared, I left Windows tablets behind (one less OS to maintain!) but kept using OneNote. While the iPad app doesn’t have as many features as the Windows version, it’s close enough for my purposes.

However, there are a few things that bother me about OneNote. For one, it seems designed to keep you in OneNote. While it’s easy to share notes with other OneNote users, it’s not easy to export to other formats. On the Mac version, you can save individual pages as PDFs. However, you can’t export whole notebooks or notebook sections. Converting your notebook to PDFs page-by-page is tedious, especially when you’ve accumulated almost a decade’s worth of information.

But more importantly (for my purposes, at least), OneNote enforces a strict hierarchy: you write in pages, which are in sections, which are in notebooks. Over time I’ve developed a consistent structure for dealing with all three levels of the hierarchy, making it relatively easy for me to find things. However, it’s not easy to surface non-hierarchical relationships between the more granular elements in the system (i.e., pages.) Yes, there are links and tags. However, they’re not as flexible or granular as I’d like.

As a result, my OneNote information repository structure is much more hierarchical and chronological than I’d like. For example, while I can easily see the sequence of notes I’ve captured for a particular project, I can’t easily see patterns in notes between projects. I wish I could easily surface themes emerging in my work, or re-visit related ideas I’ve come across in the past. OneNote asks that I keep those connections in my head. It’s a missed opportunity.

When I interviewed Beck Tench for The Informed Life podcast last year, I learned about Zettelkasten, a way of taking notes that comes closer to what I’d like. Some tools seem well-suited to this way of capturing knowledge, such as DEVONthink and Roam Research. Recently I’ve also discovered the concept of “digital gardening,” which is a useful frame to think about the problem. (This post by Tom Critchlow is a good entry point.)

Traditional note-taking applications, such as OneNote and Evernote, take their structural cues from paper-based notebooks. Digital doesn’t have the same constraints as paper. It’s possible to build a digital note-taking system that allows connections to emerge over time, rather than be imposed from the top-down at the start. While such a system needs some tending (hence the garden metaphor), it does things that paper can’t do. I’m very excited about the possibilities.