What I Learned From a Year of Directed Reading

Last year, I wrote a piece called “Thirty Books I Want to Read Before I Turn Thirty.” The somewhat eclectic list actually consisted of twenty-four books, with empty slots left to add six more as the year went on. Roughly two-thirds of the books were well-known classics, while the remainder were contemporary fiction or non-fiction.

Although I’ve always read articles and the like voraciously, I neglected books until recently, and my knowledge of the “great books” was nearly nonexistent. The goal of this project was to remedy that. As I wrote last year, “Online articles can be a decent substitute for books on non-fiction topics of immediate interest, but only rarely do they touch on the human condition in a deep way… As I look at gaps in my own knowledge and thinking, I appreciate the value of deliberate undertakings.”

The project succeeded, although I still have much more reading to do. Here are some of the lessons I learned.

  1. Literature changes and improves as you get older. The Odyssey has far more layers than I noticed in eighth grade. I always imagined literature as a vehicle that allows the naïve to understand foreign experiences (“There is no frigate like a book…”) But at 16, I hardly understood my own life and struggled to appreciate how it resembled or differed from the books I read. Literature benefits multiplicatively from the richness of my own experiences. My teenage self could never have appreciated Anna Karenina as much as I do now, five years into my marriage. This is a compelling reason to reread books. I barely remembered The Odyssey, but even if I remembered every line, rereading it with a new perspective would be worthwhile.

  2. Much of contemporary social science formalizes knowledge that we’ve had for a long time. If I wanted to earn a PhD in behavioral economics, I would open a Jane Austen book to a random page, pick a random sentence, and then design a study that uses the behavior of a dozen Harvard undergrads to “prove” the wisdom contained in that sentence. Literature gets many things wrong, but the filter of centuries is far more exacting than peer review. The inhabitants of past centuries weren’t idiots, even if they couldn’t express their ideas in contemporary scientific language.

  3. Reading literature takes practice. Anna Karenina is my favorite book I read last year, and it was unbelievably difficult to get though. The book took me 20 hours of reading time cover to cover, sprinkled across 9 months. (I took a few months off in the middle and then restarted from the beginning.) I couldn’t read it for more than about 45 minutes at a time without falling asleep or becoming restless. For years, I failed to cultivate my ability to concentrate on a single piece of writing, and so it atrophied. By the end of the year, though, I was simply better at reading. With reading as with running, I find that consistent practice allows me to move faster and keep at it for longer. And as with running, I hope to never be so “out of shape” again.

  4. Revealed preferences are real. There was one particular Sunday morning last June that I earmarked for reading Anna Karenina. I was on vacation and had nothing else to do. But instead of Russian literature, I found myself opening a copy of Elements of Statistical Learning. (It’s an iconic, ludicrously dense textbook that develops the mathematical foundations of machine learning.) I deeply believe that I’ve underinvested in reading literature and I’m proud of my effort to read more, but there’s a reason my degrees are in math and computer science rather than literature.
  5. Structure is valuable. Put this down as another lesson that I learned from reading and from running. I can absolutely guarantee that I wouldn’t have made it through Anna Karenina or Crime and Punishment without having committed to both books beforehand.
  6. Facebook is actually pretty great. When I wrote my initial article about reading thirty books, I only shared it via Facebook. All sorts of people – friends, family members, and acquaintances – commented on my list and added their own suggestions. Strikingly, this didn’t just happen on Facebook. I had multiple conversations over the course of the year – with my uncle, or with a friend, or with a friend’s father – where they brought up the list I’d shared and added their own recommendations. It’s fashionable to hate on Facebook, and I only visit the site for a few minutes a few times a week, but it facilitated some of the most meaningful conversations I’ve had in the last year.

The lessons I listed above are more important than the actual checklist of results, but I do feel obligated to shared that progress report.

First off, I actually did find books for the last six slots:

Jorge Luis Borges: Labyrinths

Each of these short stories is deeply thought provoking. I enjoyed this one immensely.

Tom Wolfe: The Electric Kool-Aid Acid Test

Tom Wolfe is one of my favorite authors, and while The Right Stuff and The Bonfire of the Vanities are both superior to this book, it’s still worthwhile. There’s an unabashedly countercultural thread in Silicon Valley’s history that is no longer extant, and I wonder how the tech industry will be diminished as that legacy fades further into the past. That said, by the end of the book I was thoroughly tired of Ken Kesey and all of the Pranksters.

G.K. Chesterton: The Innocence of Father Brown

Another enjoyable compilation of thought-provoking short stories.

James C. Scott: Seeing Like a State

This book left an impression that feels disproportionate to its quality. I thought the book was OK, and that it was at its best when it crystallized seemingly obvious ideas. However, since I finished the book, I’ve found myself constantly thinking about its themes. Here’s a piece I wrote applying some of those arguments to understand Google's impact on the internet.

Tyler Cowen: Big Business: A Love Letter to an American Anti-Hero

I read much of what Cowen writes and consider him an excellent thinker, which is why I feel comfortable saying this was well below his usual standards.

Pearl S Buck: The Good Earth

I read this book in high school and picked it up again on a whim. I got more out of it than the first time around, but I can’t recall thinking of it since I put it down.

In addition to these six books, I make a couple substitutions: Terry Pratchett’s The Truth in exchange for The Colour of Magic, and the entire George Smiley series in exchange for Call For the Dead. John le Carre’s books became my default low-effort reading last year, and they filled that role admirably.

I’ll also admit that I didn’t finish my whole list. The books I failed to read were largely ancient classics (I only finished The Odyssey) or pieces of philosophy or criticism. I’m still working on The Theory of Moral Sentiments, but it’s a challenging read. The Closing of the American Mind was a surprisingly disappointing book, largely because the disputes it addresses – so relevant to the culture wars of the 80’s – all seem long resolved. In truth, I abandoned it after a tedious passage discussing the evils of the “orgasmic” rhythms of rock music. By contrast, the first chapter of The Western Canon still feels extremely relevant. However, I skipped the bulk of the book since I got very little out of Bloom’s commentary on books I haven’t read. I’ll revisit this book in the future after reading more Shakespeare and Milton.

I couldn’t stand the title character of Emma and abandoned it half-way through. I may still force myself to finish it, though, if only to improve my knowledge of behavioral economics. Finally, I couldn’t find versions of the two Shakespeare plays that work well with my preferred formats (Audible or Kindle) and never got around to picking up physical versions.

I’m incredibly pleased that I put together and explicit reading list for last year, and I plan to compile a similar list for 2020, even if the year is well underway. Please let me know if you have any suggestions!