Reading, Wisely


Readwise is a utility that’s changed the way I read. I'm thoroughly enjoying it and I recommend it to anyone looking to improve their learning. You can sign up for a trial here:

Readwise - plain link (opens in a new tab)

Readwise - my referral link (opens in a new tab)


Readwise is an app (browser extension, web app, mobile app) that organizes information from the books you read. The app relies on learning techniques like spaced repetition (opens in a new tab) to train your memory on your reading highlights and annotations.



Readwise makes it easy to retain information you’ve read and deemed important in the past. I try to read constantly, but when I look at my Books list, there are plenty of subjects that are blurry or shockingly, missing altogether from my memory. I’ve been a Kindle device/app enthusiast and previously built my own scripts to export and organize my highlights. It was fun, but I ended up spending more time writing the so-called automation than actually reviewing the highlights. Readwise handles all of the syncing automatically from all your ebooks and articles, and even supports input from physical books. Its Daily Readwise review feature is a daily, randomized feed of highlights that surfaces old and new content to train on.

Making New Connections

There is a thrilling feeling when your mind makes connections between two seemingly disparate topics. This is foundational in my belief in [liberal arts education][4] and it's applications. The simple act of viewing highlights from multiple, unrelated books in the Daily Readwise allows your brain to play with these concepts on the same plane. Readwise’s tagging feature allows you to group highlights about the same topic or theme, so you can build your knowledge base with more examples and perspectives. Both of these features aid in constructing, expanding, and applying mental models to the world, or what Charlie Munger called a “latticework” (opens in a new tab) of models from different disciplines.

How I Use It

Set Up

I mostly use the core Readwise syncing sources:

  1. Kindle - automated
  2. Pocket - automated
  3. Non-kindle ebooks - semi-automated, requires one manual step when I finish a book
  4. Physical books - manual, but with highly reliable OCR.

There are also other a growing number of non-traditional sources like Twitter threads and podcast annotations. I haven’t tried them out yet, but they look promising.

The default settings are thoughtfully done to maximize your learning right out of the box (e.g. 5 daily items, mix of old and new highlights). You can get really granular configuring these settings, down to the book/article level. So far, I’ve only used this to filter out certain things, like definitions from a Javascript textbook I read in 2012.

Developing a Review Habit

The best product experiences create new habits and rituals around them, for a positive result. Readwise has created a few distinct habits for me. I look forward to my Daily Readwise and it’s one of the few things I let myself do on my phone when waking up. This takes less than a minute and is easy to implement. I never have to schedule in time for this and I never miss it.

Readwise sits on my home screen and I’ve started to open it whenever I need a “feed fix”. It takes my boredom trigger and offers something more valuable than a dopamine hit. Sometimes I’ll do a few cycles of 5 items before calling it quits and going back to whatever I was supposed to be doing.

Developing Better Reading Habits

Readwise has also changed the way I read. I now look for insights that I want to extract and return to later far more deliberately. I’ve found that even for books I abandon, if I was able to pull a single interesting idea out of it, I got some value out of it. This has reduced the guilt of putting down a book that can’t hold my attention. Or in the case of many business books, lets me extract the primary bits in the beginning without slogging through the filler.

The same applies to how I approach articles. I now view all types of text as holding information I can extract for my own purposes. I'm excited to uncover items to clip and have been delighted by the easy inputs into Readwise, including: highlighting directly in my browser, copy/pasting text from a mobile app, or taking an image of a physical book or magazine. This lets me jot things down, like book recommendations, without having to leave the text and pick them up later.

Organizing Information

I’ve always liked the idea of linking ideas together and this was lacking in my homegrown version of this tool. In addition to notes, you can also add freeform tags to your highlights. This makes it easy to view all your highlights that relate to theme like writing or decision-making. I use this feature to learn about a specific topic. I’m very interested in learning about the routines and processes of interesting creators, and I’ve started to aggregate tags for routine and process for instance.

I use the Daily Review to tag anything that fits into my ongoing areas of interest.

Last Word

I was happy to drop my hacky version for a simple, easy, and well-designed product. It's helping me to create better habits and reinvigorating my reading pracitce.

I'm training myself to spend on well-designed software products so that such things can exist. Unfortunately paid apps are still a boundary for many - and hopefully the COVID trend of increased subscription spending will change that. For me, the $8.99 / month is well worth the increased utility from books I’ve already purchased (usually for the low Amazon set price of $9.99). I’m sure this was intentional: get more out of your books for less than the already low price of a book a month. Better yet, it makes me excited to buy and read more books.

Of course, if you want to apply these lessons to a self-hosted system you can. You can scrape (pun intended) together your own version by parsing the Kindle Cloud Reader (and other reading apps) to a database (including no-code databases in Notion, Airtable, and even Google Sheets) and building out the necessary views. Or you can keep it lo-fi. I’ve heard of several non-fiction authors using a index card based version of Readwise, where they group passages from different sources by them. I wouldn’t be surprised if this tradition influenced Readwise's card ui and tag features.

And then you could always take it further. While many in the organized thinking movement (or roamcult (opens in a new tab)) are using Readwise’s Notion and Roam exports to develop fully mapped information on everything, I find the Readwise experience to be fully satisfactory on its own.