Outlining Books for Learning

Outlining Books for Learning

My learning process is one of mining words for insights that I can structure into a form that my brain can understand. I revisit my outlining process to try to find a way to make it more efficient.


Every once in a while I come across a book that excites me so much that I want to absorb it in a structured manner so I can properly test the ideas in the field. The first book I outlined in such a fashion was an advance copy of Tim Ferriss’ [The Four Hour Work Week][4hww]; the concepts in it were so novel and plentiful that I needed some way of keeping them straight in my head. Unfortunately, I have a poor memory and a somewhat ad-hod note taking process. So today, I’m taking a break from my Groundhog Day Resolutions definition to figure out what I can do to improve it.

Past Learning Challenges

When I was a student, I was a terrible note-taker because I didn’t have a clear idea of what the key goals were. I had the vague idea that I was supposed to memorize and reproduce facts on demand, a task that I found so tedious that I became rather resistant to everything that smacked of rote learning. The first problem was that I always skeptical of facts presented without a context I could intuitively and/or viscerally grasp; this was a great barrier to memorization, because my mind wasn’t receptive. Nevertheless, I took notes in a somewhat-futile attempt to learn in the classroom. My recollections of classroom instruction and homework all the way through my first four years of college are ones of hazy concepts and unclear goals. It was only in coursework for which I had innate curiosity that engaged, and then I would hit the second challenge: figuring out exactly what the lecturer/reading material was trying to say. I suppose partly this was my fault, as I was often not being up-to-speed on the supporting lessons of the distant past.

The problem for me has always been ambiguity of purpose in the material; the context for understanding key concepts and mapping the relationship between concepts and procedure were often lacking in a form that I could use. Of course I didn’t know back then that this was the problem in my learning process, but I think the kind of work I do now is a reaction to those years of confusing immersion in poorly-designed and presented instructional experiences. I hate that feeling of not understanding something that someone is trying to teach me by repeating the same recipes over and over again.

When I realized that it was just my way of understanding the world and not stupidity, my learning process became one largely of translating existing material into a form that I could be manipulated more easily by my type of brain. The book outlining is one of those translation processes.

The Purpose of Outlines

What I like about outlines is that they present an overarching view of the subject material. For example, when I’m at the bookstore looking for new programming books, I evaluate each book by reading the Table of Contents. The Table of Contents (TOC) of a book is a 10,000 foot view of the author’s understanding of the subject, and you can infer a lot from the title of the chapters and the order of their presentation. A great TOC will actually teach you something about the subject, because the chapter titles will give away information and supply contextual information about what is important to the author. A crappy TOC will read like the ingredient list of a food product you’ve never tasted; you can see that there’s stuff in there you recognize, but you have no idea what it might be like. You just know there’s a bunch of stuff in it. That’s a sign that the author has approved the book as an exercise in taking inventory of his/her knowledge of the subject. This seems to be a typical approach. When the Table of Contents reads like a poem, that’s an indicator that a curious and engaged mind is eager to tell me how it all flows together; that book is more likely to be useful in teaching me new concepts.

When it comes to advanced topics, I assess the TOC for its ability to break the subject down into useful conceptual areas, the subsystems that together comprise a greater interconnected system of understanding. In TOCs that also provide subchapter listings, I look for identification of key objects and conceptual landmarks; every field seems to have from 3-7 key pieces that, once identified, help me carve the material into meaty fillets of understanding. Every field has a subfield, and so complexity grows with increasing detail. If one can maintain clarity of identity, relationship, and scope of applicability for each item of understanding presented, you end up with a great working roadmap of the field; when I see this in a Table of Contents, I get very excited.

My Purposes

In outlining a book, I’m essentially trying to create a detailed mental table of contents that will act as the framework for accurate understanding. The purpose behind this, however, is to augment my own evolving framework of self-knowledge, which goes beyond the contents of a single book and encompasses the sum total of my life experiences. That would be a pretty interesting diagram to create, now that I think about it, but for the purposes of this discussion I’ll limit the outlining process to what applies to my current obsession with Mihali Csikszentmihalyi’s 1990 book Flow:

  • Accurate capture of the overarching key concepts as I understand them, with page numbers and quotes, so I can reference them accurately in future writing.
  • Create a thematic roadmap of each chapter, because each chapter appears to be a hub to an entire different world of exploration.
  • Collect the interesting stories and citations.
  • Develop a personal understanding of how the book is relevant to what I’m doing now.
  • Be able to convey key bits of the book to associates who would find them interesting, with supporting citation.

Behind these goals are two basic desires:

  • To create a useful, well-designed reference. Not because I’m so good, but because there’s so much bad stuff out there. It’s one of my moral imperatives.
  • To make that reference available to people. Because I don’t like the feeling of being frustrated in finding good reference, I don’t want other people to go through the same feeling.

I’m pretty intrigued by Flow right now because it is answering a bunch of questions that I’ve tried to answer for years. I had found the book difficult to get into before because it takes its time introducing the subject and direction of inquiry, and stylistically the personable-yet-distant tone of the writing lulls me to sleep. Ironically, one of Csikzentmihalyi’s main observations is that many people have lost the ability to “order consciousness” and “psychic energy” to achieve greater levels of fulfillment; so my snooziness makes me a prime example of this trend. Damn!

Anyway, there is quite a lot of material here to sort through, and I perceive that all of it is important. It’s already very well structured, but if I want to internalize it I need to create my own structure that is compatible with my needs. Creating a good outline is my first pass.

My Outlining Experiences

I’ve outlined only a few books to date, having been content with half-remembering good ideas in the past. The only one I distilled into my own mental framework was [my review on The 4 Hour Work Week][4hww]. It’s a pretty long, tedious process, and I’m wondering what I can do to make it more efficient. Or if I’m being really honest with myself, just how to make it faster and easier without compromising my purposes or standards. I think this means adopting a multi-pass approach to reading, using the purposes I outlined (accurate capture, thematic roadmap, etc.) to set different reading goals. It’s like being a human multi-pass compiler, creating useful object code from each pass to compile a more optimal executable of understanding.

When I outlined T4HWW, I actually sat in my bed typing the important passages into a word processor over a couple of nights. Then, I used that transcription as the outline for the

[4hww], going back and forth between the book to fill in gaps of my understanding as I tried to explain it. The result was that I learned the material on-the-fly, and became aware that certain attitudes and approaches were possible, but I didn’t commit any of the material to memory. That was probably enough at the time, as I mainly found the book exciting because it opened my eyes to new possibilities in “independent lifestyle design”–a lot of my current plans have been seeded with the ideas from this book. One nice side effect of the blog as outline approach was the ensuing high level of discussion in the blog comments. That’s always nice to have.

The second book I outlined was The Freedom Manifesto, which was recommended by my sister after it had cheered her up on a particularly grim day of commuting from Boston’s South Station. The book is essentially a manifesto against accepting that current society’s highly-commercialized and materialistic nature has our best interests at heart, choosing instead to live free of soul-destroying automation . It’s a fabulous book, filled with stories and calls to action, and is rather thicker book than The Four Hour Work Week, so the outlining process I had used was taking quite a bit longer. One day at Starbucks I was complaining to my BFF Erin about the tedium of the entire note-taking process, and she glibly asked why the hell I didn’t just use a highlighter. I stared blankly at her for several long seconds as the sheer practicality of this sunk in, wondering why I had never thought of it. There is part of me that thinks of books as sacred, and it used to really annoy me when I checked out a library book that had been “personalized” by the previous reader. And I used to hate writing in blank notebooks, which I realized undermined the purpose of having them. However, in that moment I realized I could think of books as working copies for mining understanding, a kind of pre-printed note paper. Thus freed of my preconceptions, I got as far as distilling each chapter into a brief set of master chapter descriptions. They’re handwritten in one of my notebooks, but now the process of transcription awaits me. I haven’t yet mustered the energy to do so.

The third book I outlined was Stumbling On Happiness, which I’d picked up after hearing an interview with the author on National Public Radio. However, I didn’t read it for a long time because I kept giving away my copy to people. I’d started it multiple times, but like Flow I found that it took its time to establish its premise, the narrative wended its leisurely way through numerous side stories, citations, and interesting tidbits. Like Flow, it’s actually quite an enjoyable book once I reset my expectations of pacing to one compatible with, say, Sense and Sensibility. Anyway, after finally getting going I again found that there were innumerable useful insights scattered throughout it, each of them applicable to multiple aspects of my working and personal life; it’s essentially a treatise of how the innate processes of our brain make our pursuit of happiness fraught with self-delusion and fallacious understanding. It’s quite remarkable. Armed with the highlighter tip, I dove in and started marking passages that I found particularly pivotal. And that’s as far as I got. One cool thing about using the highlighter is that I can pick up the book and skim it rapidly for interesting insights. What is missing, however, is the overarching structure that transforms those insights into a set of working principles that can be applied in practice. So the book sits, highlighted, but not yet reduced even to the chapter descriptions I’d done for The Freedom Manifesto.

The fourth book is Flow, and I have actually stopped outlining it because the very act of outlining was preventing me from getting into the book. And this is why I’m writing this process post now.

The Multi-Pass Approach Under Consideration

What I’m thinking of doing is reading in several stages. As a reader, I tend to skim very rapidly because I enjoy reading for ideas and events. It’s the rare book that will force me to slow down and enjoy the passages as they are literally transcribed. For The Freedom Manifesto and Stumbling On Happiness, I attempted to force myself to read more slowly to better absorb the material in a studious manner, but as I’ve intimated before this approach just doesn’t work for me. What I think what will actually work is committing to reading the book multiple times for different purposes. Is this a trick I didn’t learn as a young’un? Anyway, here’s what I’m thinking:

PASS 1: FRAMING – Skim very rapidly to figure out what the book is trying to say. Where is it starting? What are the underlying premises? What are the key claims? How is it supporting the claims? What does the book conclude? Use highlighter to put a dot in the margin, and use bookmarks to tag the critical pages. There usually aren’t that many of them; the insight-mapping pass will come later. The result of Pass 1 is a loose framework of the book’s major ideas and how they link together. You would think that the synopsis printed on the back of the book should accomplish this, but there’s an annoying tendency for the back-of-the-book claim it’s interesting without giving anything away. At the end of this pass, write a synopsis and try to figure out the author’s own perspective, background, and training based on the book, by chapter. This is invaluable when trying to understand the key arguments later, and to infer what the missing assumptions are (if any).

PASS 2: FRAMEWORK BUILDING – The second pass through the book is more leisurely, and now that I have some idea of what the book is trying to say and how it’s saying it I can spend more time considering the arguments in each chapter. Now I can use the highlighter to mark actual passages that I think are relevant to understanding the supporting mechanics behind each claim and conclusion. How is the author making each point? What is the reasoning and justification behind each point? Are the links clear to me? The result from this pass is, ideally, a transcribed list of citations that fills in the framing I did in PASS 1 as a Word document, which will later become critical source material for synthesizing my own thoughts on the material. It’s helpful to have it all in one place.

PASS 3: NARRATIVE CAPTURE – Every book has some good anecdotes in them, and I find that in day-to-day conversation I like to pass them on to people I’m talking to. This pass is another fast scanning of the material, by now familiar territory from the first two passes, to find the good stories. This is something I haven’t done before, but I would probably use a different color highlighter to mark them for later citation or transcription.

At this point, I have marked everything I need to convert what I’ve gotten from the book into new source material for my own work. However, I’ve only conceptually solved the problem: the bottleneck is getting the marked passages into digital form. Some solutions I’ve tried or am considering:

  • Use my voice transcription software to capture the passages I read aloud. I’ve used Dragon Dictate 7, and have been surprised at how effective it is in understanding me. Recognition speed is vastly better than I remember, and being able to say “Page 4: passage quote blah blah blah New Paragraph” is pretty neat, because using the dictation software with a headset leaves your hands free to hold the book and maintain eye contact with it. On the down side, tricky passages with odd vocabulary require a lot of manual correction, and doing it through voice command leaves something to be desired. Plus, to ensure accurate transcription I end up shifting my attention to the screen and back to the book to confirm accuracy, which ends up being the major loss of efficiency.

  • I could get one of those portable digital recorders and then use a foot pedal control / video logging product (shameless plug: like buddy company Inquirium‘s InqScribe software) to capture what I’ve read aloud. Advantages of this approach is that with a foot pedal, my hands are free to focus on typing and my eyes stay on the screen. My feet handle replaying the audio, and my ears can concentrate on listening.

  • I could also find a transcription service and email them the audio file, and hope that the transcription is accurate.

  • I could photocopy each page and cut the results up into snippets I paste up on a big piece of cardboard. But that is pretty old-school. Would be fun for smaller books or individual chapters, though.

  • I’ve seen ads for portable OCR scanners that look like giant pens, so you can theoretically grab lines of text as easily as “highlighting” them straight from the book. OCR products tend to give me the willies because they seem to not be very reliable, but it has been ten years since I have last played with it. Perhaps there has been some improvement in the reliability and ease of use. Not that I am very hopeful; I saw some business card scanning software recently and it looked like it was 10 years old. Clunky, clunky, clunky.

  • I could possibly buy or illicitly acquire an e-text version of the book, but then I would have to reread it to find all my highlight marks. The advantage of paper is that it’s much easier to index through physical means.


p>I don’t want to do this for every book I read, of course. The point of all this activity is to create a working set of ideas that I can re-purpose and restructure into a new set of design principles. I find that I work well if I can have everything in one manipulation space. For ideas that have no direct visual analog, that space (for me) is a Word or Adobe InDesign document. InDesign is a great idea space because it allows me to visually organize the text more easily than Word. Plus, I can use the typographic controls to make them look nice, which is one of my personal aesthetic requirements.

Then, after all of this is done, I can do this:

PASS 4: LEISURELY READ – After some time has passed, it’s nice to read the book again and see what different insights flicker across my mind.

So that’s what I’m thinking right now. How do y’all do it?