To me, this is not only one of greatest books ever written but perhaps the only book of its kind. Just imagine: the private thoughts of the most powerful man in the world, admonishing himself on how to be better, more just, more immune to temptation, wiser. It is the definitive text on self-discipline, personal ethics, humility, self-actualization and strength. If you read it and aren’t profoundly changed by it, it’s probably because as Aurelius says “what doesn’t transmit light creates its own darkness.” You HAVE to read the Hays’s translation. If you end up loving Marcus, go get The Inner Citadel and Philosophy as a Way of Life by Pierre Hadot that studies the man (and men) behind the work. And if you want more on the topic, Marcus inspired my book The Obstacle is the Way.
2. Letters from a Stoic by Seneca
After Marcus Aurelius, this is one of my favourite books. While Marcus wrote mainly for himself, Seneca had no trouble advising and aiding others. In fact, that was his job—he was Nero’s tutor, tasked with reducing the terrible impulses of a terrible man. His advice on grief, on wealth, on power, on religion, and on life are always there when you need them. Seneca’s letters are the best place to start, but the essays in On the Shortness of Life are excellent as well. You can draw a pretty straight line from Seneca to the essays of Montaigne (also read: How To Live, a biography of Montaigne) to the modern day writings of Nassim Nicholas Taleb (read: The Black Swan, Fooled By Randomness and The Bed of Procrustes).
3. Man’s Search for Meaning by Viktor Frankl
Frankl is one of the most profound modern thinkers on meaning and purpose. His contribution was to change the question from the vague philosophy of “What is the meaning of life?” to man being asked and forced to answer with his actions. He looks at how we find purpose by dedicating ourselves to a cause, learning to love and finding a meaning to our suffering. His other two books on the topic, Will To Meaning and Man’s Search for Ultimate Meaning have gems in them as well.
4. 48 Laws of Power and Mastery by Robert Greene
There is no living writer (or person) who has been more influential to me than Robert Greene. I met him when I was 19 years old and he’s shaped me as a person, as a writer, as a thinker. You MUST read his books. His work on power and strategy are critical for anyone trying to accomplish anything. In life, power is force we are constantly bumping up against. People have power of over us, we seek power ourselves that we might be free enough and influential enough to accomplish our goals—so we must understand where power comes from, how it works and how to get it. But pure power is meaningless. It must be joined to mastery and purpose. So read his book Mastery so that you can figure your life’s task and how to dedicate yourself to it.
5. & 6. Letters from a Self-Made Merchant to His Son by George Horace Lorimer and Letters to His Son by Lord Chesterfield
These two books of letters are great—I wish my father had written me stuff this good. The first book is the (supposedly) preserved correspondence between Old Gorgon Graham, a self-made millionaire in Chicago, and his son who is coming of age and entering the family business. The letters date back to the 1890s but feel like they could have been written in any era. Honest. Genuine. Packed with good advice. Chesterfield wrote his letters to his illegitimate son, tutoring him on how to learn, how to think, how to act, how to deal with important people. I don’t agree with all his advice but most of it is great.
7. Average Is Over: Powering America Beyond the Age of the Great Stagnation by Tyler Cowen
In terms of business/economics, this is one of the more important books I’ve read in a long time. I even keep a framed passage from it on my wall (it also inspired the apiece of writing I am proud of). Cowen’s books have always been thought provoking, but this one changes how you see the future and help explain real pain points in our new economy–both good and bad. Although much of what Cowen proposes will be uncomfortable, he has a tone that borders on cheerful. I think that’s what makes this so convincing and so eye opening. A hollowing out is coming and you’ve got to prepare yourself (and our institutions) as best you can.
8. & 9. Tiny Beautiful Things: Advice on Life and Love from Dear Sugar by Cheryl Strayed and Bird By Bird: Some Instructions on Writing and Life by Anne Lamott
It was wonderful to read these two provocative books of essays by two incredibly wise and compassionate women. Cheryl Strayed, also the author of Wild, was the anonymous columnist behind the online column, Dear Sugar and boy, are we better off for it. This is not a random smattering of advice. This book contains some of the most cogent insights on life, pain, loss, love, success, youth that I have ever seen. I won’t belabour the point: read this book. Thank me later. Anne Lamott’s book is ostensibly about the art of writing, but really it too is about life and how to tackle the problems, temptations and opportunities life throws at us. Both will make you think and both made me a better person.
10. The Score Takes Care of Itself by Bill Walsh
A few years ago, I read The Education of a Coach, a book about Bill Belichick which influenced me immensely (coincidentally, the Patriots have also read my book and were influenced by it). Anyway, I have been chasing that high ever since. Bill Walsh’s book certainly met that high standard. Even if you’ve never watched a down of football, you’ll get something out of this book. Walsh took the 49ers from the worst team in football to the Super Bowl in less than 3 years. How? Not with a grand vision or pure ambition, but with what he called the Standard of Performance. That is: How to practice. How to dress. How to hold the ball. Where to be on a play down the very inch. Which skills mattered for each position. How much effort to give. By upholding these standards—whatever they happen to be for your chosen craft—success will take care of itself.
I don’t read fiction for fun—I try to read novels that express some fundamental part of the human condition or some hard won truth. I hope you’ll enjoy these (though for a fuller list, read my article on the 24 Fiction Books That Can Change Your Life).
11. Fight Club by Chuck Palahniuk
I’m amazed how many young people haven’t read this book. Truly life-changing. This is the classic of my generation; it is the book that defines our age and ultimately, how to find meaning in it. It’s a cautionary tale too—about being too caught up in revolutionary ideas.
12. The Moviegoer by Walker Percy
The Moviegoer is exactly the novel that every young kid stuck in their own head needs to read. The main character—who lives in New Orleans just a few blocks from where I lived—is so in love with the artificiality of movies that he has trouble living his actual life. The Moviegoer—it is like a good Catcher in the Rye but for adults. Just a perfect book. An equal cautionary tale: The Sorrows of Young Werther by Goethe.
13. & 14. What Makes Sammy Run? and The Harder They Fall by Budd Schulberg
Budd Schulberg’s (who wrote the screenplay for On the Waterfront) whole trilogy is amazing and each captures a different historical era. His first, What Makes Sammy Run? is Ari Gold before Ari Gold existed–purportedly based on Samuel Goldwyn (of MGM) and Darryl Zanuck. His next book, The Harder They Fall is about boxing and loosely based on the Primo Carnera scandal. All you need to know about Schulberg’s writing is captured in this quote from his obituary: “It’s the writer’s responsibility to stand up against that power. The writers are really almost the only ones, except for very honest politicians, who can make any dent on that system. I tried to do that. And that’s affected me my whole life.” Fiction can do that, and sometimes it does it even better than non-fiction.
15. The Apprenticeship of Duddy Kravitz by Mordecai Richler
What a book. It’s not as good as What Makes Sammy Runbut it’s so damn good. “A boy can be two, three, four potential people,” Duddy’s uncle tells him, “but a man is only one. He murders the others.” Which potential person will you be? Which part of you will you allow to rule? The part that betrays your friends, family, principles to achieve success? Or are there other priorities?
Some other novels I like: Civil War Stories by Ambrose Bierce, Company K by William March and Invisible Man by Ralph Ellison.
One of my favourite categories of books: moral biographies. That is, the stories of great men and women in history, written with an eye towards practical application and advice.
16. Plutarch’s Lives by Plutarch
Clearly the master of this genre, Plutarch wrote biographies of famous Greeks and Romans around the year 100 AD. As always, I tend to default to the Penguin collections. I strongly recommend Plutarch’s Lives Vol. I & II, Essays, and The Makers of Rome: Nine Lives. His book On Sparta is also a collection of biographies (and aphorisms) from the famous Spartans. There is a reason that Shakespeare based many of his plays on Plutarch—not only are they well-written and exciting but they exhibit everything that is good and bad about the human condition. Greed, love, pain, hate, success, selflessness, leadership, stupidity—it’s all there.
17. The Lives of the Most Excellent Painters, Sculptors, and Architects by Giorgio Vasari
A friend and peer of Michelangelo, Da Vinci, Raphael Titian and all the other great minds of the Renaissance sat down in 1550 and wrote biographical sketches of the people he knew or had influenced him. What I like about this book is that the profiles are not about statesmen or generals but artists. There are so many great lessons about craft and psychology within this book. The best part? It was written by someone who actually knew what he was talking about, not some art snob or critic, but an actual artist and architect of equal stature to the people he was documenting.
18. Totto-Chan: The Little Girl at the Window by Tetsuko Kuroyanagi
The book has sold something like 5 million copies in Japan alone (an insane number). Totto-Chan is a special figure in modern Japanese culture—she is a celebrity on par with Oprah or Ellen, with a magazine, news show and exalted position to boot. The book describes a childhood in pre-WWII Japan as a poorly misunderstood girl who obviously suffered from attention disorders and excess energy. It wasn’t until she met a special school principal—unlike any I have ever heard of—who finally GOT her. And I mean understood and cared about and unconditionally supported her in a way that both inspires me and makes me deeply jealous. If only all of us could be so lucky…
19. Titan by Ron Chernow
I found Rockefeller to be strangely stoic, incredibly resilient, and, despite his reputation as a robber baron, humble and compassionate. Most people get worse as they get successful, many more get worse as they age. In fact, Rockefeller began tithing his money with his first job and gave more of it away as he became successful. He grew more open-minded the older he became, more generous, more pious, more dedicated to making a difference.
20. The Power Broker by Robert Caro
It took me 15 days to read all 1,165 pages of this monstrosity that chronicles the rise of Robert Moses. I was 20 years old. It was one of the most magnificent books I’ve ever read. Moses built just about every other major modern construction project in New York City. The public couldn’t stop him, the mayor couldn’t stop him, the governor couldn’t stop him, and only once could the President of the United States stop him. But ultimately, you know where the cliché must take us. Robert Moses was an asshole. He may have had more brain, more drive, more strategy than other men, but he did not have more compassion. And ultimately power turned him into something monstrous.
21. Sherman: Soldier, Realist, American by B.H Liddell Hart
This was someone I knew little about before I read the book, and by the end of it found myself referencing and thinking of him constantly. It is equal parts due to the greatness of the man himself and to Hart’s vivid and engrossing portrait. I almost feel like I have lost something not having known this of him my whole life. There is a stunningly profound quote from Hart in the book that I’ll paraphrase here that defines his genius: Sherman’s success was rooted in his grasp that the way to success is strategically along the line of least expectation and tactically along the line of least resistance. It is that kind of thinking that immediately displaces any preceding notions about Sherman’s reputation as a general or a legend. All these myths belies his strategic acumen, his mastery of terrain and his deep understanding of statesmanship and politics. There is much to learn from the man and this biographer—who himself was a great strategist and mind.
– My Bondage and My Freedom by Frederick Douglass and The Autobiography of Malcolm X, two of the most inspiring men of the last 150 years. (also in this vein, My Life and Battles by Jack Johnson and Up from Slavery by Booker T. Washington)
– The Rise of Theodore Roosevelt by Edmund Morris. Dr. Drew recommended this book to me, it is spectacular. He’s my favourite president.
The Fish That Ate the Whale: The Life and Times of America’s Banana King by Rich Cohen The book sucked me in completely. Everyone I’ve recommended it to loves it.
–Asylum: An Alcoholic Takes the Cure and No Hiding Place by William Seabrook (I actually ended up helping get Asylum back in print if you want to hear that story)
For more biography recommendations from me, see this list.
I don’t believe that philosophy is something for the classroom–it’s something that helps you with life. As Epicurus put it: “Vain is the word of the philosopher which does not heal the suffering of man.” I’ve already recommended a couple of practical philosophy books in different sections but a couple more worth reading:
22. The Moral Sayings of Publius Syrus
A Syrian slave in the first century BC, Publius Syrus is a fountain of quick, helpful wisdom that you cannot help but recall and apply to your life. “Rivers are easiest to cross at their source.” “Want a great empire? Rule over yourself.” “Divide the fire and you will sooner put it out.”
23. Essays and Aphorisms by Arthur Schopenhauer
Schopenhauer is a brilliant composer of quick thoughts that will help us with our problems. His work was often concerned with the “will”–our inner drives and power. “For that which is otherwise quite indigestible, all affliction, vexation, loss, grief, time alone digests.” But he also talks about surprisingly current issues: “Newspapers are the second hand of history”–and that the hand is often broken or malfunctioning. And of course, the timeless as well: “Hope is the confusion of the desire for a thing for its probability.”
24. Fragments by Heraclitus
While most of the other practical philosophy recommendations I’m making are bent towards hard, practical advice, Heraclitus might seem a bit poetic. But those beautiful lines are really the same direct advice and timeless, perspective-changing observations as the others. “Try in vain with empty talk / to separate the essences of things / and say how each thing truly is.” “Applicants for wisdom / do what I have done: / inquire within.” “Character is fate.” “What eyes witness / ears believe on hearsay.” “The crops are sold / for money spent on food.”
25. Rules for Radicals and Reveille for Radicals by Saul D. Alinsky
This is the 48 Laws of Power written in more of an idealist, activist tone. Alinsky was the liaison for many civil rights, union and student causes in the late 50’s and 60’s. He teaches how to implement your radical agenda without using radical tactics, how to disarm with words and media as opposed to arms and Utopian rhetoric.
26. Boyd: The Fighter Pilot who Changed the Art of War by Robert Coram
Boyd was probably the greatest post-WWII military strategist; he developed the F-15 and F-16, revolutionized ground tactics in war and covertly designed the US battle plans for the Gulf War. He shunned wealth, fame, and power all to accomplish what he felt needed to be accomplished. Coram captures his essence in a way that no other author has touched.
Of course you also need to read 33 Strategies of War by Robert Greene, The Book of Five Rings by Musashi, The Strategy Paradox by Raynor, Machiavelli’s The Prince, and Von Clausewitz’ On War.In terms of classics, The History of the Peloponnesian War is an obligation for every student of history.
For a whole list of books on the US Civil War, start here. For a more complete list of recommendations see my list of 43 Books About War and 24 Books To Hone Your Strategic Mind.
As important as philosophy and moral fiction are, they’re just ideas if they’re not counterbalanced with an understanding of our biology and psychology.
27. The Moral Animal by Robert Wright
This is probably the definitive beginner text on evolutionary psychology and one of the easiest to get into. It’s a little depressing at first, realizing how ruthless many of our so called “good” feelings are. But then you realize that truth is better than ignorance, and you emerge seeing the world as it truly is for the first time. Also, a similar read is Why Beautiful People Have More Daughters, which is more of a Q&A approach to the subject and has contemporary edge.
28. Sex on the Brain by Deborah Blum
One of the better books on evolutionary biology that focuses almost entirely on the biological and psychological differences between men and women. It’s written by a journalist (who cites scientists) so it’s easy to read if you’re not studied in the field. If you want to get into evolutionary psychology–which you totally should–this is a good starting point because it covers all the basics. Essentially, it discusses how men and women have benefited evolutionarily through different behaviours and strengths so it would only make sense that they would have developed into two very different entities.
I would also recommend: The Game by Neil Strauss (as well as The Truth), The God Delusion by Richard Dawkins, The Evolution of Desire by David Buss, and The Origins of Virtue by Matt Ridley which asserts that we had morality before religion, trade before capitalism and cooperation before government.
Instead of giving descriptions for these, I’m just going to list titles. You need to read ALL of them. Especially the ones marked with an*, as they are the ones the illustrate the darker side of the web.
29. Here Comes Everybody: The Power of Organizing Without Organizations by Clay Shirky
30. The Pirate’s Dilemma by Matt Mason
31. You Are Not a Gadget: A Manifesto * by Jaron Lanier
32. The New New Thing by Michael Lewis
33. Founders at Work by Jessica Livingston
(interviews with technology founders from one of the best investors of all time)
34. The Net Delusion: The Dark Side of Internet Freedom * by Evgeny Morozov
35. Hackers and Painters: Big Ideas from the Computer Age by Paul Graham
36. Wikinomics: How Mass Collaboration Changes Everything by Don Tapscott
37. The Cathedral and the Bazaar: Musings on Linux and Open Source by Eric S Raymond
38. Brave New War: The Next Stage of Terrorism and the End of Globalization * by John Robb
Some of the most pleasurable books I’ve read in my life belong in the genre of narrative non-fiction—epic true stories and sagas that are almost too good to believe.
39. The Tiger: A True Story of Vengeance and Survival by John Vaillant
Holy shit, this book is good. Just holy shit. Even if it was just the main narrative—the chase to kill a man-eating Tiger in Siberia in post-communist Russia—it would be worth reading, but it is so much more than that. The author explains the Russian psyche, the psyche of man vs. predator, the psyches of primitive peoples and animals, in such a masterful way that you’re shocked to find 1) that he knows this, and 2) that he fit it all into this readable and relatively short book. The story is nuts: a tiger starts killing people in Russia and a team is sent to kill it (Russia is so fucked up, they already have a team for this). At one point, the tiger is cornered and leaps to attack the team leader…and in mid-air the soldier’s rifle goes into the tigers open jaws and down his throat all the way to the stock, killing the tiger at the last possible second. Wow. (His other book The Golden Spruce is also great)
40. The River of Doubt: Theodore Roosevelt’s Darkest Journey by Candice Millard
I thought I knew about Theodore Roosevelt. This book opens with him stranded in the Amazon jungle begging his son to let him kill himself so he wouldn’t be a burden on their exploring party any longer. And then it gets better from there. I mean, did you know he is credited with being the first to chart and navigate a totally unknown river as long as the Nile? And that he did that after he was President, just for fun? I’m not sure I need to explain much else, but if you needed more convincing, I will say that Candice Millard who wrote Destiny of the Republic (which I highly recommend) wrote this too and it’s better than her last book. Not only is there a bunch of great history and drama here, it shows a human side of Roosevelt I had not understood before.
41. Endurance: Shackleton’s Incredible Voyage by Alfred Lansing
50 plus years old, this is a story that more than stands the test of time. Sir Ernest Shackleton makes his daring attempt to cross Antarctic continent but his crew and boat are trapped in the ice flows. What follows are 600 days of harrowing survival, first from the elements, then from hunger, then from the sea as he makes a daring attempt in a small lifeboat to reach land 650 miles away, then again as he struggles over land and mountains to bring relief to his men. And when he finally arrives with it, Shackleton simply boards them on the boat and returns home as if nothing had happened. He was an immensely brave man in the midst of terrible adversity and we see this so clearly in a book based on the remarkable diaries of his men. He never quit, never seemed to despair. This book (and his life) were living proof of his family motto: “Fortitudine vincimus” (By endurance we conquer).
42. Shadow Divers by Robert Kurson
This book is a work of art. It is like The Tiger-good. A diver (whose life principles we can all learn from) and a ship captain find the wreck of an unknown German U-Boat in 1991…on the coast of New Jersey. That’s a thing? Apparently. And they spend the next five years diving the wreck 230+ feet underwater until they identify it. This book is narrative nonfiction writing at its finest. Please read.
As you have probably gathered, I’m a bit of a nerd. I didn’t graduate from college but I still love to read the classics and I’m slowly making my way through them. I thought I’d put together a quick list that everyone should check out:
43. The Aeneid by Virgil (translated by Robert Fagles)
I made an effort to read some classical poets and playwrights few years ago. The Aeneid was far and away the most quotable, readable and memorable of all of them. There’s no other way to put: the story is AMAZING. Better than the Odyssey, better than Juvenal’s Satires. Inspiring, beautiful, exciting, and eminently readable, I loved this. I took more notes on it that I have on anything I’ve read in a long time. The story, for those of you who don’t know, is about the founding of Rome. Aeneas, a prince of Troy, escapes the city after the Trojan War and spends nearly a decade wandering, fighting, and trying to fulfil his destiny by making it to Italy. I definitely recommend that anyone trying to read this follow my tricks for reading books above your level (that is, spoil the ending, read the intro, study Wikipedia and Amazon reviews, etc.).
44. Candide by Voltaire
I read this book as I waited for my wedding to start. It might seem like a strange choice, given that it’s a 200 year old book mostly about unimaginable hardship, torture, death and misfortune. Somehow, despite this, the book is a light hearted satire that pokes fun at optimism, philosophy, politics, and power. In the end, Voltaire concludes, all we can do is tend to our own garden. Il faut cultiver nos jardins.
45. The Epic of Gilgamesh by Unknown
I read this on my honeymoon (probably the only person on the beach reading it, if I had to guess). Especially when I learned after that a new introduction paragraph had been discovered only recently. His tomb may have been found recently too. Imagine if Homer’s works had only been discovered in the mid 1800’s after being lost to history for thousands of years. How crazy would that be? Reading the classic epics can feel like work but there is value in it. These works are timeless and universal. Such a great line
He will face a battle he knows not,
he will ride a road he knows not.
46. Epigrams by Martial These are hilarious. I have one hanging on the gate in front of my house. Martial also served as a partial inspiration for my writing on the Canvas Strategy.
47. Hamlet by Shakespeare ]
Philosophy runs through this play–all sorts of great lines. There are gems like “..for there is nothing either good or bad, but thinking makes it so” which I used in my last book and “Beware of entrance to a quarrel; but, being in, bear it, that the opposed may beware of thee.” was a favourite of Sherman.
48. Satires by Juvenal
These are bitter, sarcastic attacks on Rome. They partially inspired my book Trust Me, I’m Lying.
I also love Seneca’s plays, Joseph Addison’s Cato, Shakespeare’s Julius Caesar, Demosthenes and Cicero’s speeches.