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This is Part 1 of a 3-part series. You can find Part 2 here, and Part 3 here.

For the longest time, I’d read non-fiction voraciously, only to forget nearly all of the information that I had thought I acquired. I felt like I learned something by completing an article or book, but when I went to apply what I thought I learned, nothing was there.

Why read anything if I won’t retain any of it?

My goal when reading is to generate knowledge and insights that can be connected with knowledge and insights derived from other sources. That is a mouthful to say that I want to integrate information from something I read and connect it to my existing knowledge.

I strongly believe in approaching everything I do as a craftsman does their trade. I’m a knowledge worker, so building a system to help me build and connect knowledge is imperative to my success and personal goals, but I suspect that such a system will be useful to anyone that wants to expand their knowledge.

Three main actions happen to each article, book, etc. that I read:

  1. Reading
  2. Collecting
  3. Synthesizing

When you’re reading you’re actively consuming information. You converse with the book’s author, you highlight important information, and write about your ideas, arguments, and inspirations.

Then you start collecting all of that into a system that allows for connecting that information to other information you’ve previously stored.

These steps help you with the most important step: synthesizing. This is where you connect information, discover new insights, and generate ideas.

As you integrate this workflow, you’ll find that you’ve opened up the flow of ideas. This increased flow reduces the friction to create, which is the “final expression of an idea”. Whether you create an article, an application, or begin a new habit, creativity is the ultimate display and realization of your mastery of an idea.

But to generate ideas, you first need to come into contact with an outside idea or bit of knowledge. Reading is one of the best ways to do that.


“Some books should be tasted, some devoured, but only a few should be chewed and digested thoroughly.”

  • Sir Francis Bacon

The seminal text for how to read a book is the aptly titled How to Read a Book. In it, the authors explain the four levels of reading:

  1. Elementary: the largely mechanical reading you first learn, where individual words are understood.
  2. Inspectional: this level of reading communicates superficial knowledge, and is the most common type of reading done. There are two related methods of inspectional reading that you can use to help you determine if you want to read the book further and at which level you want to read:
    • Systematic skimming where you look at the title, preface, table of contents, index, and publisher’s blurb. If you still aren’t sure if you want to read it, you can skim a few paragraphs of important-seeming chapters.
    • Superficial reading is a technique for difficult books where you read all the way through without stopping, then if you wish you can revisit the difficult portions for a more complete understanding.
  3. Analytic: this level of reading is done for understanding. Within this level there are three stages, each of which comes with a set of rules to follow:
    • Find out what the book is about by:
      1. Classifying the book.
      2. Stating what the whole book is about as briefly as possible.
      3. Outlining the individual parts of the book, then outline the book as a whole.
      4. Identifying any problems the author tries to solve.
    • Find out what the book says by:
      1. Identifying and defining the author’s key terms.
      2. Identifying and understanding the most important sentences to identify the author’s propositions.
      3. Identifying the author’s arguments.
      4. Identifying which of the identified problems the author solves and which they did not. For those that they did not, decide which ones the author knew they were unable to solve.
    • Criticize the book as a communication of knowledge by:
      1. Interpreting and outlining the book before criticizing it.
      2. Disagreeing calmly.
      3. Presenting good arguments for any critical judgment you make - this shows your criticism is based on knowledge rather than opinion.
      4. Showing where the author is uninformed, misinformed, illogical, or incomplete for any criticism.
  4. Syntopical: this is the most demanding type of reading, and involves reading multiple sources to synthesize your own knowledge.

These levels of reading and the rules that comprise them are expanded on very thoroughly in the book, and I highly recommend it.

The vast majority of reading you will do will be inspectional, but if you decide you want to go deeper, following the rules of analytic reading will help you gain a deeper understanding of the book’s subject matter.

No matter the level you decide to read, reading should be treated as a conversation between you and the writer. The way you converse with the writer - whether of a book, article, essay, or some other piece - is by highlighting important passages and writing relevant notes.


Highlighting is intensely personal: only you will know what’s important to you. But conversations are two-way, so you should look out for what is important to the writer.

Bolded or italicized text, strongly declarative sentences, and summaries are all good signposts of highlightable passages. Highlights should inform your conclusions, be used as references in later summaries, and communicate important knowledge from the author.


A lot happens with notes. In dead-tree books, don’t be afraid to write in the margin. In electronic books and articles, most reader software includes note-taking functionality. But what should you take notes on? Here are a few things that I commonly find myself writing:

  • Questions: What is unclear to me? What would I ask the author? What philosophical questions do I have?
  • Context: Sometimes you need additional context for a highlight, or you thought of something else you read that you want to link to a particular passage, or you have some background knowledge that rounds out what you’re reading. Contextual notes are some of the most important notes to take.
  • Ideas and inspirations: If contextual notes are the most important, ideas and inspirations might be the most fun. Sometimes you will come across a passage that unlocks something in your mind, it inspires you to action, it gives you a blueprint of how to do something more effectively. Write this down immediately! Flashes of inspiration are precious things, don’t let them go to waste.

Another exercise for effective reading I came across recently is the blank sheet method, detailed by Farnam Street. With this method, you will mind map everything you know about a topic on a blank sheet of paper before beginning the book. Because you have to have some understanding of what the book is about first, it’s best to do this for analytical reading after systematic skimming and finding out what the book is about.

At the close of each reading session, add to your mind map anything you learned using a different color. Review this before starting a new session and periodically when done with the work.


Reading is not just a skill but a craft, and a craft always deserves some good tools. Here are the ones I use and recommend:

  • Instapaper - I use Instapaper for all online articles and papers I read. While its reader isn’t always perfect, the ability to highlight, take notes, and automatically sync with Readwise (more on that later) makes it a standout in the space. Pocket is also great, but it lacks the ability to add notes while reading.
    • Update: I’ve moved a lot of my article clipping to Matter which has a gorgeous interface and a number of useful reading and subscription tools. For RSS feeds, I am a big fan of InoReader.
  • Calibre - This is the ultimate electronic library management app. It can fetch and manage metadata, organize your collection, send to specific devices, even host your library on a server. I primarily use this to manage my non-Kindle ebooks and send them to my iPad for reading, but it also has a built-in reader.
    • Update: I am now using the Mac-only DevonThink for this and all my document management workloads. If you have a Mac, you’ll find it extremely useful, if overwhelming.
  • Kindle - I use Kindle for iOS for most of my e-Book reading. It handles PDFs and other files competently (although Calibre autoconverts files before sending them to Kindle) along with native Kindle books. The highlighting and note-taking functions are top-notch.

Reading is just the first step in this journey. You’ve taken notes, you’ve highlighted, you’ve had a conversation with a long-dead author, and you’ve learned a few things. Now, you need to make those things stick. Join me next time for Part 2 of My Information Operating System: Collecting.