In a similar post a couple months ago, I talked about taking an app I’ve had for a long time (OmniFocus, in that case) and “doubling down” on it—making it a more regular part of my daily life.

It occurred to me today that Instapaper is another such app. I’ve used—and paid for—Instapaper since it was Marco Arment’s indie app debut. But for the last few years, I have steadily added articles to my Instapaper queue but rarely gone into the app and actually read what was in there.

In this way, it’s been similar to OmniFocus: an aspirational graveyard of things I want to do but never get around to doing.

That’s a shame, and it could be an argument for abandoning the thing wholesale, but I’d rather turn back to it and try to re-engage. I’ve said it before, and I’ll say it again: this year I’m trying to be less all-or-nothing. Less, “I didn’t do this thing I wanted so I’d better quit trying.” If something doesn’t work, you could toss it in the bin. But an alternative is… to keep trying until it works.

As for Instapaper: I want to build a process around reading things, making notes and annotations on them, and then archiving those (or publishing them!) somewhere, and doing that regularly. Two antipatterns I’m fighting against:

  1. I find things I want to read, but never read them. This is exemplified by having pages open in Safari tabs on my Mac or iPhone for months—months—and never, ever reading them, only to lose them when I reset something.
  2. I read things… and then quickly forget about them, adding them to the background noise of my brain. Sure, some of that stuff gets synthesized, or sloshes around disembodied until one day it generates something interesting… but I’d rather have a system for capturing my thoughts on something as soon as I read it. Like journaling, but for the shorter-form stuff I come across every day.

And there are three types of content that fit nicely into Instapaper:

  1. Articles that people send me links to, or that I otherwise stumble across, on the web
  2. Posts on sites that I subscribe to via RSS, but don’t feel like reading in my RSS reader (that’s usually long-form stuff, like Ben Thompson’s Stratechery)
  3. (This was just pointed out to me today) Email newsletters that I don’t actually want to read in my email client. I’ve been considering setting up a whole separate address just to receive newsletters, to filter them out from all the other stuff that accumulates in my inbox, but shunting those things into Instapaper could be a great alternative

So this suggests a potential process I would like to start doing:

  1. Route all of the three content types above into Instapaper1
  2. Here’s the missing piece: on a regular basis, read the content in my Instapaper queue!
  3. Annotate what I read in Instapaper with highlights and notes
  4. When I’m done reading an article, export my annotations into Ulysses
  5. Archive the article in Instapaper
  6. Either file the Ulysses note in a searchable index of annotations, and/or publish it somewhere (like, on this site, right here)

The iOS Instapaper app is particularly good at handling steps 3-5. The missing pieces for me have tradtionally been:

  • I don’t read my queue on a regular basis (I usually ignore the Instapaper app entirely unless I’m on a plane…)
  • I don’t do anything with the notes I export (they accumulate in my Ulysses inbox, making it one more endless closet full of junk that’s intimidating to process…)

So how can I patch these holes? When there’s a thing that requires a little effort on a regular basis, the solution is generally build a habit.

A couple ways to build these habits:

  1. Schedule a regular time, both to read Instapaper (I could do it over coffee in the morning, for example, or in late afternoon when my brain is mostly dead anyway), and to format and publish my notes2
  2. Chain the new activity to an existing activity, see the mention of coffee above (I already tend to read email or whatever I came across on the intertron while I drink coffee in the morning), or every time I sit down on public transit I look at Instapaper instead of whatever else I do on my phone…

Having said all of this (and this post has pretty much been me thinking out loud, I hope it’s useful… or even, in retrospect, coherent 😏), I have a couple actions I can take3:

  1. Set up an email filter that shunts some of the newsletters I’m subscribed to to the Instapaper email address that exists for that purpose
  2. Schedule a time to read Instapaper for X minutes
  3. Create a template for posting my annotations from an Instapaper article
  4. Schedule a time to post annotations from 1 article
  5. Create entries in Streaks or somewhere similar to reinforce the habits above

Well, then! This all sounds good, doesn’t it? Let’s see if I actually do it. Watch this space. 🤔

  1. An issue I’ve found when routing things to Instapaper from my Mac is the routine failure of the Javascript bookmarklet in Safari to work the way it’s supposed to. I haven’t figured out if this is due to a plugin conflict, or what… but it does exert some negative pressure against saving everything I want to Read Later to Instapaper. Update: Instapaper now has a Safari extension, installed via the Mac App Store, which I suspect will be more reliable than using the bookmarklet. So I’m back in business for this bit! 👍🏼 ↩

  2. Formatting and publishing the notes would be much easier given a simple template and process for doing so. Right now they just go into Ulysses with the vague thought that “I’ll do something with that, someday.” ↩

  3. Which actions should go into OmniFocus… if you think I’ll actually use it! ↩