The Classics: Books That I Re-Read

What is a classic? Here is Thomas Cleary’s definition from his translation of The Art of War:

“On a small scale, a classic yields significantly different meanings when read in different circumstances and moods; on a large scale, a classic conveys wholly different worlds when read in different times of life, at different stages of experience, feeling and understanding of life. Classics may be interesting and even entertaining, but people always find they are not like books used for diversion, which give up all of their content at once; the classics seem to grow wiser as we grow wiser, more useful the more we use them.”

​When I first came across this idea I began to think about what books I considered to be my own classics. I came up with, over several days, a list of twenty five and I shared them. You can see them here. But that list is wrong.

See, I created that list by sitting and thinking about the books that had impacted me. But who am I to say which books have impacted me, and how, and why? How can I know which texts are my classics? Aside from spurious and biased recall—which is corrupted by, 1) my immediate surroundings, and 2) recent media consumption, writing and conversation—how can I determine, accurately and reliably, what books have and do matter to me? The answer is simple, and I suspect that’s why I overlooked it for so long: count.

I’ve seen it bandied around recently that the only books worth reading are those you would re-read. The idea is that the books that you re-read hold some sort of personal significance that cannot be extracted in one sitting. As Cleary said, “the classics seem to grow wiser as we grow wiser, more useful the more we use them.” So it follows that our own personal classics can be discovered merely by determining which books we have re-read, and how often we’ve revisited them.

That’s what I’ve done here. Rather than creating a bullshit reading list designed to show off the breadth and depth of my study, and add even more “must-reads” to your reading pipeline, I have, to the best of my ability, gone back through my reading history and made note of every single book I’ve ever re-read since I was a teenager For now, I have just listed the titles and authors. But eventually, I hope to write an essay on each entry on the list which explores why I’ve felt compelled to re-read it and how it’s content has (or hasn’t) altered my life.

But before we get to the actual list, here are some notes on the list itself:

The most re-read books are at the top. Recency of re-reads is not accounted for; only frequency matters here. So a book re-read ten times five years ago appears higher on the list than a book I re-read twice last year. Total re-reads, contained in brackets next to the title, are mostly estimates as I didn’t began noting finishing dates until about two years ago. Whole numbers indicate a linear, start-to-finish read-through. A .5 indicates heavy reference/use in my own writing and projects, or a significant amount of casual browsing, flicking and contemplation. Finally, the list has not been doctored in any way for any particular audience. There are no omissions, inflations or subtractions. All titles and totals are accurate to the best of my knowledge.

These books are, according to a quantifiable standard, my classics.

Meditations by Marcus Aurelius (10.5)

The Complete Harry Potter Series by J.K. Rowling (5.5)

The Art of War by Sun Tzu (4.5)
Antifragile by Nassim Taleb (4.5)
The Lord of the Rings Trilogy by J.R.R. Tolkien (4)

Nicomachean Ethics by Aristotle (3.5)
Letters from a Stoic by Seneca (3.5)
The Hobbit by J.R.R. Tolkien (3)
Never Let Go by Dan John (3)
The Black Swan by Nassim Taleb (3)

The Complete Essays by Michel de Montaigne (2.5)
Thinking, Fast and Slow by Daniel Kahnemann and Amos Tversky (2.5)
Reveille for Radicals by Saul Alinsky (2.5)
Rules for Radicals by Saul Alinsky (2.5)
The Four-Hour Work Week by Tim Ferriss (2.5)
Mastery by Robert Greene (2.5)
The 48 Laws of Power by Robert Greene (2.5)
The 33 Strategies of War by Robert Greene (2.5)
The Autobiography of Malcolm X by Malcolm X and Alex Haley (2)
The War of Art by Steven Pressfield (2)
Turning Pro by Steven Pressfield (2)
The Complete Jack Reacher Novels by Lee Child (2)
Influence by Robert Cialdini (2)
Zorba the Greek by Nikos Kazantzakis (2)
The Sword in the Stone by T.H. White (2)
Fight Club by Chuck Palahniuk (2)
Starting Strength by Mark Rippetoe (2)
Fooled by Randomness by Nassim Taleb (2)
The Persian Expedition by Xenophon (2)
​The History of the Peloponnesian War by Thucydides (2)

The Power Broker by Robert Caro (1.5)
The Years of Lyndon Johnson by Robert Caro (1.5)
The Story Grid by Shawn Coyne (1.5)
Thoughts of a Philosophical Fighter Pilot by James Stockdale (1.5)
Philosophy as a Way of Life by Pierre Hadot (1.5)
The Collected Works of Kahlil Gibran (1.5)
Value Proposition Design by Alex Osterwalder and Yves Pigneur (1.5)
Business Model Generation by Alex Osterwalder and Yves Pigneur (1.5)
Small is the New Big by Seth Godin (1.5)
The Dip by Seth Godin (1.5)
​The Way to Love by Antony de Mello (1.5)
The Four-Hour Chef by Tim Ferriss (1.5)
The Pocket Oracle and the Art of Wisdom by Baltasar Gracian (1.5)

(Last updated: 16/03/17)

“What books have most influenced you?”

​That seems like a good question to ask someone you look up to or find interesting. But I think there’s a better question. One that will yield more unexpected, and possibly, more fruitful answers. “What books have you re-read?”

It’s the question I now like to ask people when broaching the topic of books, and it’s the same question I’m going to ask you, right now. I’ve shared my re-reads, my classics.

What are yours?