A Decent Digital Commonplace Book System

For as long as I can remember, I’ve been looking for a sustainable commonplace book system. My ideal system would be:

1. Broad. Because I read online articles and ebooks in equal measure, an ideal system would address both.
2. Effortless. If I highlight a passage anywhere, I want it to be stashed automatically. Any system that requires manual transcription or entry is a system that won’t last long.
3. Discrete. For maximum recombinability, I want each highlight to be stored individually, with a reference back to the larger work.
4. Associative. I want highlights to resurface in my life opportunistically.
5. Durable. Platforms come and go, but I want my highlights to last forever.

So far, my quest has been futile. Sure — once every few months, I’ll go down an evening-long rabbit hole and emerge on the other side with some new tools and workflows that seem promising. Sometimes, a tool will stick on its own merits. (Evernote is one tool that made it through the gauntlet.) But when it comes to complete systems, I’ve had little luck.

Until now! Tonight’s rabbit hole took me to a good place. Not a perfect place, but a place that’s exciting enough to outline in public.

My Commonplace Book System, For Now

1. Kindle highlights get exported to Evernote as individual notes via Clippings.io. Since Clippings.io doesn’t — yet? — run in the background, I’ve set a reminder to email me once every two weeks with a nudge to initiate collection and export.
2. Instapaper highlights get exported to Evernote as individual notes via IFTTT.

That’s it!

Background

Three preconditions in my life make this system possible:

1. 90% of the books I read, I read on Kindle.
2. I’ve been on a continuous Evernote kick for the past 1.5 years. Because of its proven utility (for me) and persuasive (to me) corporate philosophy, I’m comfortable relying on it. I’m also already a premium subscriber, so I never worry about running out of space. Plus, Evernote’s contextual notes feature helps related highlights to edge into my peripheral vision at opportune moments, addressing my goal of associativity.
3. I want this badly enough that I’m willing to pay for it.

Three recent rediscoveries unblocked me:

1. Instapaper is amazing. I’ve known this for a long time — I even wrote a love letter to Instapaper three years ago — but when Betaworks bought the app, it fell off my radar for a while. Recently, though, a colleague was singing the praises of Pocket, the other main “read-it-later” service. And I thought — hey, maybe I should get serious about reading things later again. While going down the mini-rabbit hole of setting up Pocket, I came across this article by Marius Masaler comparing Pocket and Instapaper, wherein he concludes “I may have been using the wrong service all along” — the wrong service, for his needs, being Pocket. One of the key Instapaper features Marius mentions is…highlighting! Specifically, “a Kindle-like way to delineate and keep the best passages from an article.” I dimly remember hearing about this feature a while back, but Marius’s article jogged my memory at just the right time for me to take action.
2. IFTTT is the bomb. No surprise there. IFTTT is an elegant, powerful way to daisy-chain APIs. By hitching the Instapaper API to the Evernote API, I was able to assemble this recipe to export Instapaper highlights to Evernote. Each highlight is stashed in more-or-less-real-time, complete with a link to the source.
3. Clippings.io got good. Amazon doesn’t offer an API of your Kindle highlights, much to my sadness, so a recurring theme of my rabbit hole quests has been “how in the world will I get my highlights out?” Clippings, which advertises itself as a way to “organize the notes you make on your Kindle,” is now my best answer. This isn’t the first time I’ve come across Clippings; the last time I went down the commonplace book rabbit hole, I ran into it while searching something like “export Kindle highlights to Evernote.” Clippings was okay back then, but the bookmarklet that collected Kindle highlights felt brittle, and I never fully integrated it into my workflow. I rediscovered Clippings today while running a similar search, and was very impressed by how far it’s come. The Clippings Chrome extension now works like a dream, and I’m heartened that they’re collecting a monthly subscription fee (just $1.99); this gives me hope that they’ll be able to afford continued development even for this admittedly-niche need. The Evernote export functionality is also excellent, fulfilling my wish for discrete notes that each link back to the larger work.

Fine Print

As I mentioned, the system’s far from perfect. I have three modest wishes for the future:

1. Dear Amazon: please make a Kindle highlights API!
2. Until then: dear Clippings, I hope you’ll consider adding a “collect and export highlights in the background” option to your Chrome extension. Even just a periodic notification on the extension icon would help.
3. As long as I’m dreaming: Clippings, I’d very much like the option to name each note with the book’s title in addition to the quotation’s location. Also, a blank line between the end of the quotation and the citation.

Total cost of the system: ~$10 / month

1. Clippings.io Chrome extension subscription: $1.99 / month.
2. Instapaper Premium, which lifts the “5 highlights per month” cap: $2.99 / month. (Bonus: the website accepts payment via Stripe.)
3. Evernote Premium, which I use for lots of other things, too: $5 / month.

How Does the System Stack Up?

1. Broad. ★★★★☆ Between Instapaper and Kindle, I estimate that I’ll be able to catalog 80% of all my reading.
2. Effortless. ★★★☆☆ Better than ever, but the need to manually trigger Clippings.io is not ideal.
3. Discrete. ★★★★★ Individual notes in Evernote with links back to the original source — yes! As close to a shoebox of index cards as digitally possible.
4. Associative. ★★★☆☆ Evernote’s Context feature gets me most of the way there, but I’d still like to find a way to extend the associativity beyond the boundaries of Evernote.
5. Durable. ★★★★☆ I trust Evernote as much as I trust any service, due to their strong export functionality, viable business model, and corporate philosophy. The missing star represents general healthy skepticism of any business’s ability to stick around and stay good forever.
6. Overall: ★★★★☆ (76%). Not bad!

Why Go Down All These Rabbit Holes At All?

Reading is the most reliable way I’ve found to reenergize myself. I read a lot already, but I want to read even more, and knowing that every reading session emanates useful information helps the act to feel more intentional.

Many of the thinkers I most admire seem to keep formidable clip files, and collecting highlights is how I lay the groundwork for writing I’m proud of. I want to stash other people’s ideas in a single place where they can tangle and braid.

The most basic truth, though, is that I find it endlessly satisfying to stitch services together to meet my needs. Doing so helps me to understand myself and my tools more deeply. Getting this close to realizing the dream is intoxicating, but I’m guessing the next rabbit hole is hiding not too far ahead.