Setting up a new note-taking system

This weekend I invested a bunch of time in researching note-taking systems and applications — I want to get in the habit of both writing more and maintaining a repository of things I’ve thought about and learned and the quarantine seems like a good idea to really sink some time into these sorts of organizational tasks (I’m also experimenting with a new email client Airmail and have been working hard to get better code linting set up in my main text editor).

I took a few notes on some note-taking philosophies and the applications that are purpose-built for note-taking (focusing on macOS) which I’ll share here.


I’ve been greatly influenced by the idea of the memex developed by Vannevar Bush and of the better-phrased “bicycle of the mind” (RIP Steve Jobs) and have wanted for a long time to implement such a system for myself — while I’m a compulsive highlighter in my Kindle, Pocket, and Zotero apps, I practically never actually go back to review those highlights. Occasionally they come in handy when I know that I want to review some article and I can quickly check the highlights to see what’s most important, but I don’t have a good organic way of reviewing things I’ve found interesting over time or, for example, reviewing highlights by subject.

Stephen Johnson writes about the tools he uses for writing in the article Tool for Thought from 2005 in the NYTimes:

The raw material the software relies on is an archive of my writings and notes, plus a few thousand choice quotes from books I have read over the past decade: an archive, in other words, of all my old ideas, and the ideas that have influenced me.

I would write a paragraph that addressed the human brain’s remarkable facility for interpreting facial expressions. I’d then plug that paragraph into the software, and ask it to find other, similar passages in my archive. Instantly, a list of quotes would be returned: some on the neural architecture that triggers facial expressions, others on the evolutionary history of the smile, still others that dealt with the expressiveness of our near relatives, the chimpanzees. Invariably, one or two of these would trigger a new association in my head — I’d forgotten about the chimpanzee connection — and I’d select that quote, and ask the software to find a new batch of documents similar to it. Before long a larger idea had taken shape in my head, built out of the trail of associations the machine had assembled for me.

Similar in objective if not in implementation is the Zettelkasten method for collecting and cross-linking notes on things you’ve read or ideas you’re working on. In general the ideas can be boiled down to:

  • Be deliberate about capturing your thoughts and ideas, and don’t be too precious about what’s considered a complete thought
  • Store them in a cross-referenced and searchable system that allows for both browsing and discovery

So I want to start moving toward a system more similar to this — where I can compile and store my notes from different projects and (hopefully) promote better recollection of these thoughts and ideas as well as additional spontaneous connections.


The tools I considered are:

I was looking for an application to check a few important boxes:

  • macOS and iOS native support
  • Markdown support
  • Beautiful interface I enjoy using
  • A tagging / cross-linking system (as opposed to foldering)
  • Support for multiple media types (images, pdfs, etc)

Here are my notes on each (I ended up going with Bear)

Evernote (free / $8 per month)

Evernote is the oldest of these apps and probably the most popular — Ezra Klein is a big proponent and the key feature seems to be the clip-from-browser extension and the oceans of integration for sending data to Evernote. This didn’t feel write for me because I want an app that promotes writing rather than being a passive receptacle for things I read on the internet — that being said I’m still considering setting up Evernote to be the one-true-receptacle and funneling all of my highlights from Kindle, Pocket, and Zotero there. But that’s a project for a future weekend.

Notion ($4 per month)

Notion was a strong contender — they’ve made a really cool product and the flexibility of the tool is very impressive. However, the PMs at notion definitely seem to be headed in a collaboration and project-management direction which doesn’t really fit my use-case at all. I would definitely consider Notion for my startup if I was doing a lot of collaboration and complex project-oriented tasks.

Bear ($1.50 per month)

I landed on Bear for three big reasons: great markdown support, a beautiful editor, and a sophisticated tagging system that allows for the idea of linking posts together in a more fluid way. So far I’m happy with the decision and have set up a global keyboard shortcut to open a new Bear note to (hopefully) encourage me to more fluidly drop into writing-mode more frequently rather than just passively reading. I’ve also pro-actively created notes for the books I’m currently reading so that (again, extremely hopefully) I’ll have reduced the friction enough to find it easy to jot down notes as I’m reading.

Ulysses ($5.00 per month)

Ulysses seems like the most beautiful of the options, and the one dedicated most to supporting writers. If I wrote professionally for a living I think Ulysses might have been a stronger contender, but for my needs (focused more on note-taking than long-form writing) Ulysses doesn’t have much on Bear and is more than 3x the price.

Roam (??? $15 – $30 per month)

Roam research is definitely the most interesting of these options. Conor White-Sullivan, the founder of Roam very explicitly lists the note-taking applications and methods I mentioned above as inspiration for Roam. The UI is focused explicitly on building a web of connections between different ideas in ways that utilize bi-directional linking and some keyboard shortcuts that encourage the user to quickly and easily create new notes and concepts.

Honestly, I would have loved to give Roam a try but at that price point it’s just not worth it for me (looking at you too, Superhuman email). My hope right now is that if Roam is successful some of the other writing apps will steal the best ideas around the UI and linking and I’ll be able to take advantage of them in a more cost-effective editor.

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By michael