“I’m not saying you have to be a reader to save your soul in the modern world. I say it helps.” walter mosley
You are reading: Ryan holiday recommended books
I’ve always devoured books. why, exactly, I’m not sure. Obviously, a big reason to read is because it’s fun. As Petrarch, a famous book lover, observed some 700 years ago, “books give pleasure to the marrow of the bones.” but if I were honest, I’d say that the real reason I’ve spent so much time with my nose in this or that book is because I’ve been looking for something: a way to life. There is a Latin expression: liber medicine animi (a book is the medicine of the soul). that’s what I’ve been looking for.
All my life and career, I have been searching, reading and taking notes in books that can teach me things. how to live. how to learn. how to find happiness how to understand the past how to prepare for the future. how to be successful. how to manage relationships how to be a good person.
I used to go around and ask every smart person I knew, even emailing important people I didn’t know, “what books do you recommend for a kid like me?” That’s how I was introduced to the Stoics. this is how I found many of the books on the list below. books about earthquakes, as tyler cowen said, that shake you to the core. Having been introduced to them by such kind and patient people, I thought I’d repay them by making a list of the books that have rocked my life and helped me become the person I am. it’s a list that has changed over time, and will continue to change, but it’s a good place to start.
choose one of them and let me take you to another. and then when you hit a dead end, go back to the list. And don’t forget to subscribe to my reading list email that recommends a new set of life-changing books every month.
books to base your life on
the meditations of marcus aurelius (amazon) for me, this is not only one of the best books ever written, but perhaps the only book of its kind. 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, more wise. is the definitive text on self-discipline, personal ethics, humility, self-actualization, and strength. If you read it and it doesn’t change you profoundly, it’s probably because, as Aurelio says, “what doesn’t transmit light creates its own darkness”. you have to read the hays translation. if you end up loving marcus, seek out the inner citadel (amazon) and philosophy as a way of life (amazon) by pierre hadot who studies the man (and men) behind the work. and if you want more on the subject, marcus inspired my book the obstacle is the way (amazon).
letters from a stoic by seneca (amazon) after marcus aurelio, this is one of my favorite books. While Marcus wrote primarily for himself, Seneca had no problem advising and helping others. in fact, that was his job: he was Nero’s tutor, tasked with curbing a terrible man’s terrible impulses. His advice on pain, wealth, power, religion and life is always there when you need it. Seneca’s letters are the best place to start, but essays on the brevity of life (amazon) are also excellent. A fairly straight line can be drawn from Seneca to Montaigne’s essays (read also: How to Live (Amazon), A Montaigne Biography) to the modern writings of Nassim Nicholas Taleb (read: The Black Swan (Amazon), Fooled by Chance (amazon) and the bed of procrustes (amazon)).
man’s search for meaning by viktor frankl (amazon) frankl is one of the deepest modern thinkers on meaning and the purpose. his contribution was to change the question of the vague philosophy of “what is the meaning of life?” to the man being questioned and forced to respond with his actions. he looks at how we find purpose by devoting ourselves to a cause, learning to love, and finding meaning in our suffering. His other two books on the subject, The Will to Meaning (Amazon) and Man’s Search for Ultimate Meaning (Amazon) also contain gems.
48 laws of power and mastery by robert greene (amazon) there is no living writer (or person ) who has been more influential to me than robert greene. I met him when he was 19 years old and he has shaped me as a person, as a writer, as a thinker. You should read his books. his work on power and strategy is essential for anyone trying to achieve anything. In life, power is the force against which we constantly collide. people have power over us, we ourselves seek power so that we can be free and influential enough to achieve our goals, so we must understand where power comes from, how it works and how to obtain it. but pure power is meaningless. it must be tied to mastery and purpose. so read his book mastery (amazon) to discover what is the task of your life and how to dedicate yourself to it.
letters from a self-made merchant to his son by george horace lorimer (amazon) and letters to his son by lord chesterfield (amazon) these two card books are fantastic. I wish my father had written me such good things. The first book is the (supposedly) preserved correspondence between old Gorgon Graham, a self-made millionaire in Chicago, and his son coming of age and entering the family business. the letters date back to the 1890s, but look like they could have been written in any era. honest. authentic. packed with good advice. Chesterfield wrote letters from him to his illegitimate son, instructing him how to learn, how to think, how to act, how to deal with important people. I don’t agree with all of his advice, but most of it is great.
average is over: pushing america beyond the era of great stagnation by tyler cowen (amazon) in terms of business/economics, this is one of The most important books I’ve read in a long time. I even keep a framed passage on my wall (it also inspired writing I’m proud of). Cowen’s books have always been thought-provoking, but this one changes the way he views the future and helps explain the 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 the cheerful. I think that’s what makes this so compelling and so revealing. an emptying is coming and you have to prepare yourself (and our institutions) as best you can.
beautiful little things: advice on life and love from dear sugar from cheryl strayed (amazon) and bird by bird: some writing instructions and life by anne lamott (amazon) it was wonderful to read these two provocative books of essays written by two incredibly wise and compassionate women. Cheryl Strayed, also the author of Wild (Amazon), was the anonymous columnist behind the online column, Dear Sugar, and boy, are we better off for it. this is not a bunch of random tips. This book contains some of the most compelling ideas about life, grief, loss, love, success, and youth that I have ever seen. I won’t press the point: read this book. thank me later. Anne Lamott’s book is ostensibly about the art of writing, but it’s really also about life and how to deal with the problems, temptations, and opportunities that life throws at us. both will make you think and both made me a better person.
the sheet music takes care of itself by bill walsh (amazon) a few years ago, i read a coach’s education (amazon), a book about bill belichick what made me it influenced immensely (coincidentally, the patriots also read my book and were influenced by it). Anyway, I’ve been chasing that high ever since. Bill Walsh’s book certainly met that high standard. Even if you’ve never seen a football game, you’ll get something from this book. Walsh led the 49ers from the worst football team to the Super Bowl in less than 3 years. What? not with grand vision or sheer 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 in a game down to the last inch. what skills mattered for each position. how much effort to give By upholding these standards, whatever they may be for your chosen craft, success will take care of itself.
fiction
I don’t read fiction for fun; I try to read novels that express a fundamental part of the human condition or some hard-won truth. I hope you enjoy them (though for a more complete list, check out my article on 24 Fiction Books That Can Change Your Life).
fight club by chuck palahniuk (amazon) I am amazed how many young people have not read this book. Truly a life changer. this is the classic of my generation; it is the book that defines our era and, ultimately, how to make sense of it. it’s also a warning: getting too caught up in revolutionary ideas.
the movie buff by walker percy (amazon) the movie buff is exactly the novel every child trapped in their own head needs to read. the main character, who lives in new orleans, a few blocks from where i used to live, is so enamored with the artificiality of the movies that he has trouble living his real life. the movie buff—it’s like a good hunter in the rye (amazon) but for adults. just a perfect book. a tale with the same moral: the sorrows of the young werther (amazons) by goethe.
what makes sammy run? and the harder they fall by budd schulberg (amazon) budd schulberg’s (who wrote the screenplay for on the waterfront (amazon)) complete trilogy is amazing, each capturing a different historical era. the first, what makes sammy run? (Amazon) is Ari Gold before there was Ari Gold, supposedly based on Samuel Goldwyn (of MGM) and Darryl Zanuck. His next book, The More They Fall, is about boxing and is loosely based on the cousin ram scandal. Everything you need to know about Schulberg’s writing is captured in this quote from Schulberg’s obituary: “It is the responsibility of the writer to confront that power. writers are really about the only ones, except for very honest politicians, who can make a dent in that system. i tried to do that. And that has affected me my whole life.” fiction can do that, and sometimes does it even better than nonfiction.
the apprenticeship of duddy kravitz by mordecai richler (amazon) what a book. not as good as what makes sammy run (amazon), but very 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. what potential person will you be? What part of you will you allow to rule? the part that betrays your friends, family, principles to achieve success? or are there other priorities?
A few other novels I like: Civil War Stories by Ambrose Bierce (Amazon), Company K by William March (Amazon), and Invisible Man by Ralph Ellison (Amazon).
biographies
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one of my favorite book categories: moral biographies. that is, the stories of great men and women in history, written with a view to practical application and advice.
lives of plutarch by plutarch (amazon) clearly the master of this genre, plutarch wrote biographies of famous greeks and romans around the year 100 ad. As always, he tends to default to penguin collections. I highly recommend Life of Plutarch Vol. I & II (Amazon), Essays (Amazon), and The Makers of Rome: Nine Lives (Amazon). His book on Sparta (Amazon) is also a collection of biographies (and aphorisms) of the famous Spartans. there’s a reason shakespeare based many of his plays on plutarch: not only are they well written and exciting, but they show all that’s good and bad about the human condition. greed, love, pain, hate, success, selflessness, leadership, stupidity – it’s all there.
the lives of the most excellent painters, sculptors and architects by giorgio vasari (amazon) michelangelo’s friend and companion, da vinci, Raphael Titian and all the other great minds of the Renaissance sat down in 1550 and wrote biographical sketches of people who knew or had influenced him. what I like about this book is that the profiles are not of statesmen or generals but of artists. there are so many great lessons on craft and psychology within this book. the best part? it was written by someone who really knew what he was talking about, not a snob or art critic, but a real artist and architect of equal stature to the people he was documenting.
totto-chan: the girl in the window by tetsuko kuroyanagi (amazon) the book has sold something like 5 million copies in japan only (a crazy number). Totto-chan is a special figure in modern Japanese culture: she is a celebrity on a par with Oprah or Ellen, with a magazine, a news show, and a privileged position to begin with. The book describes a childhood in pre-World War II Japan as a poorly misunderstood girl who obviously suffered from attention disorders and excess energy. It wasn’t until she met the principal of a special school, unlike any other she had ever heard of, that she finally caught on. And I mean I understood her, cared and supported her unconditionally in a way that inspires me and makes me deeply jealous. If only we could all be so lucky…
titan by ron chernow (amazon) i found rockefeller to be oddly stoic, incredibly resilient, and despite his reputation as a robber baron , humble and compassionate. most people get worse as they succeed, many more get worse as they get older. In fact, Rockefeller began tithing his money with his first job and gave away more as he became successful. he became more open-minded as he got older, more generous, more pious, more dedicated to making a difference.
the intermediary of power by robert caro (amazon) it took me 15 days to read the 1165 pages of this monstrosity that chronicles the rise of Robert Moses. I was 20 years old was one of the most magnificent books I have ever read. Moses built almost 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 brains, more drive, more strategy than other men, but he had no more compassion. and finally the power turned him into something monstrous.
sherman: soldier, royalist, american by b.h liddell hart (amazon) was someone I knew little about before reading the book, and in the end I found myself referring to it and thinking about it constantly. It is due in equal parts to the greatness of the man himself and to Hart’s vivid and fascinating portrayal. I almost feel like I’ve lost something by not knowing this about him all my life. there is an amazingly insightful quote from hart in the book that i will paraphrase here that defines his genius: sherman’s success was based on his understanding that the path to success is strategically along the line of least expectation and tactically along the of the line of least resistance. It’s that kind of thinking that immediately displaces any previous notions of Sherman’s reputation as a general or a legend. All of these myths belie his strategic acumen, his command of the terrain, and his deep understanding of politics and statecraft. there is much to learn from the man and from this biographer, who was a great strategist and mind.
some others:
– my slavery and my freedom by frederick douglass (amazon) and the autobiography of malcolm x (amazon), two of the most inspiring men of the last 150 years. (also in this sense, my life and battles by jack johnson (amazon) and up from slavery by booker t. washington (amazon). – the rise of theodore roosevelt by edmund morris (amazon) dr. draw recommended this book to me, it’s spectacular. he’s my favorite president. the fish that ate the whale: the life and times of america’s banana king by rich cohen (amazon) the book completely captivated me. everyone i have recommended it to loves it. –asylum: an alcoholic takes the cure and no stash by william seabrook (amazon) (I actually ended up helping get asylum back up and running if you want hear that story) for more recommendations from my bio, check out this list.
practical philosophy
I don’t think philosophy is something for the classroom, it’s something that helps you in life. As Epicurus says: “vain is the word of the philosopher that does not cure the suffering of man”. I’ve already recommended a couple of practical philosophy books in different sections, but a couple more are worth reading:
the moral sayings of publius syrus (amazons) a Syrian slave in the first century BC. c., publius syrus is a quick and useful source of wisdom that he can’t help but recall and apply to his life. “Rivers are easier to cross at their source.” “Do you want a great empire? dominate yourself.” “Divide the fire and before you can put it out”.
essays and aphorisms by arthur schopenhauer (amazon) schopenhauer is a brilliant composer of quick thoughts that will help us with our problems. his work often dealt with the “will”: our inner drives and powers. “because what is otherwise quite indigestible, all affliction, vexation, loss, pain, only time digests.” but he also talks about surprisingly topical issues: “newspapers are the seconds hand of history” – and that the hand often breaks or malfunctions. and of course, the timeless as well: “hope is the confusion of the desire of a thing for its probability.”
fragments of heraclitus (amazon) while most of the other practical philosophy recommendations I’m making lean towards practical advice and harsh, Heraclitus may seem a bit poetic. but those beautiful lines are really the same blunt advice and timeless, perspective-shifting observations as the others. “trying in vain with empty words / to separate the essences of things / and to say how each thing truly is”. “seekers of wisdom / do as I have done: / search within.” “Character is destiny.” “what the eyes testify / the ears believe by hearsay”. “crops are sold / for money spent on food.”
war/strategy books
rules for radicals and target for radicals by saul d. alinsky (amazon) these are the 48 laws of power (amazon) written in a more idealistic and activist tone. Alinsky was the liaison for many student, labor, and civil rights causes in the late 1950s and 1960s. He teaches how to implement his radical agenda without using radical tactics, how to disarm with words and means instead of weapons and utopian rhetoric.
boyd: the fighter pilot who changed the art of war by robert coram (amazon) boyd was probably the greatest later military man to the second world war strategist; He developed the F-15 and F-16, revolutionized ground warfare tactics, and covertly designed US battle plans for the Gulf War. he eschewed wealth, fame, and power to achieve what he felt needed to be achieved. coram captures the essence of him in a way that no other author has touched.
Of course, you should also read Robert Greene’s 33 Strategies of War (Amazon), Musashi’s Book of Five Rings (Amazon), Raynor’s Paradox of Strategy (Amazon), Machiavelli’s Prince (Amazon) and von clausewitz’ on war (amazon). When it comes to classics, the history of the Peloponnesian War (Amazon) is a must for any history student.
For a complete list of books on the American Civil War, start here. For a more complete list of recommendations, check out my list of 43 Books on Warfare and 24 Books to Sharpen Your Strategic Mind.
evolutionary psychology
As important as philosophy and moral fiction are, they are just ideas if not balanced with an understanding of our biology and psychology.
the moral animal by robert wright (amazon) this is probably the definitive beginner’s text on evolutionary psychology and one of the easiest to get inside. it’s a bit depressing at first, realizing how ruthless a lot 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 really is for the first time. also, a similar read is why beautiful people have more daughters (amazon), which is more of a question and answer approach to the topic and has a contemporary twist.
sex on the brain by deborah blum (amazon) one of the best 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 quotes scientists) so it’s easy to read if you don’t have a background in the field. If you want to get into evolutionary psychology, which you should, this is a good starting point because it covers all the basics. essentially, it looks at how men and women have benefited evolutionarily through different behaviors and strengths, so it would make sense that they would have evolved into two very different entities.
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I would also recommend: the game by neil strauss (amazon), (as well as the truth (amazon)), the delusion of god by richard dawkins (amazon), the evolution of desire by david buss (amazon), and the origins of virtue by matt ridley (amazon) who claims we had morality before religion, trade before capitalism, and cooperation before government.
internet
Instead of giving descriptions for these, I’m just going to list titles. you need to read them all. especially those marked with a *, since they are the ones that illustrate the darker side of the web.
here comes everybody: the power to organize without organizations by clay shirky (amazon) a brave new war: the next stage of terrorism and the end of globalization * by john robb (amazon) the pirate’s dilemma by matt mason (amazon) you you are not a gimmick: a manifesto* by jaron lanier (amazon) what’s new by michael lewis (amazon) founders at work by jessica livingston (amazon) (interviews with tech founders from one of the greatest investors of all time) the network illusion: the dark side of internet freedom* by evgeny morozov (amazon) hackers and painters: great ideas of the computer age by paul graham (amazon) (or you can read his essays here) wikinomics: how mass collaboration changes everything by don tapscott (amazon) the cathedral and the bazaar: reflections about linux and open source by eric s raymond (amazon)
narrative non-fiction
Some of the most enjoyable books I’ve ever read are in the narrative nonfiction genre: epic stories and true sagas that are almost too good to believe.
the tiger: a true story of revenge and survival by john vaillant (amazon) shit, this book is good. just holy shit. Even if it were just the main narrative, the hunt to kill a man-eating tiger in Siberia in post-communist Russia, it would be worth a read, but it’s so much more than that. the author explains the Russian psyche, the psyche of man versus predator, the psyche of primitive peoples and animals, in such a masterful way that you’re surprised to discover 1) that he knows this, and 2) that it all fits into this book readable and relatively short. the story is crazy: a tiger starts killing people in russia and a team is sent to kill it (russia is so screwed, they already have a team for this). at one point, the tiger is cornered and leaps to attack the team leader… and in the air, the soldier’s rifle enters the tiger’s gaping jaws and down its throat to the cattle, killing the tiger in the last second possible. wow. (his his another book his the golden spruce (amazon) is great too)
the river of doubt: theodore roosevelt’s darkest journey by candice millard (amazon) i thought i knew about theodore roosevelt. This book begins with him stranded in the Amazon jungle begging his son to let him kill himself so that he is no longer a burden to his scouting party. and then he gets better from there. I mean, did you know that he is credited with being the first to chart and navigate a totally unknown river as long as the Nile? And that he did it after he was president, just for fun? not sure i need to explain much more but if you need further convincing i will say candice millard who wrote the fate of the republic (amazon) (which i highly recommend) also wrote this and it is better than her last book . . Not only is there a lot of great story and drama here, but it shows a human side to Roosevelt that he hadn’t understood before.
Endurance: Shackleton’s Incredible Journey by Alfred Lansing (Amazon)Fifty years later, this is a story that more than stands the test of time. sir ernest shackleton makes his daring attempt to cross the antarctic continent, but his crew and his ship get caught in the ice flows. What follows is 600 days of harrowing survival, first from the elements, then from famine, then from the sea as he makes a daring attempt in a small lifeboat to reach land 650 miles away, then again as he battles over land and mountains. to bring relief to his men. And when she finally gets to him, Shackleton just gets them into the boat and goes home as if nothing had happened. he was an immensely brave man in the midst of terrible adversity and we see that clearly in a book based on the remarkable diaries of his men. he never gave up, never seemed to despair. this book (and his life) were living proof of his family motto: “fortitudine vincimus” (with perseverance we win).
Shadow Divers by Robert Kurson (Amazon) This book is a work of art. It’s like the good tiger. A diver (whose life principles we can all learn) and a sea captain find the remains of an unknown German submarine in 1991…off the coast of New Jersey. is that a thing? apparently. and they spend the next five years submerging the wreck more than 230 feet underwater until they identify it. This book is narrative nonfiction writing at its finest. please read.
classics:
As you’ve probably noticed, I’m a bit of a nerd. I didn’t graduate from college, but I still love reading the classics and am slowly working my way through them. I thought I’d put together a quick list everyone should check out:
virgil’s aeneid (translated by robert fagles) (amazon) A few years ago I made an effort to read some classical poets and playwrights. the Aeneid was by far the most quotable, readable, and memorable of all. there is no other way to say it: 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 than I have on everything 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 from the city after the Trojan War and spends almost a decade wandering, fighting and trying to fulfill his destiny when he arrives in Italy. I definitely recommend that anyone trying to read this follow my tips for reading books above their level (i.e. screw up the ending, read the intro, study the wikipedia and amazon reviews, etc.).
candide by voltaire (amazon) I read this book while waiting for my wedding to start. It may seem like an odd choice, given that it is a 200-year-old book that is mostly about hardship, torture, death, and unimaginable 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 our own garden. il faut cultivar nos jardins.
the epic of gilgamesh by unknown (amazon) I read this on my honeymoon (probably the only person on the beach reading it, if I had to guess). especially when I found out later that a new introductory paragraph had recently been discovered. his grave may also have been found recently. Imagine if Homer’s works were discovered in the mid-1800s after being lost to history for thousands of years. how crazy would that be? Reading the classic epics may seem like work, but it has value. these works are timeless and universal. such a cool line
“he will face a battle he does not know,
He will walk a path he does not know.”
epigrams from martial (amazon) these are hilarious. I have one hanging on my front door. martial also served as a partial inspiration for my writing on canvas strategy.
shakespeare’s hamlet (amazon) philosophy runs through this work, all sorts of great lines. there are gems like “..because there is nothing good or bad, but thinking makes it so” that I used in my last book and “be careful not to get into a fight; but, being inside, take it, so that the opposite takes care of you.” he was a favorite of sherman.
satires by juvenal (amazon) are bitter and sarcastic attacks on roma. partially inspired my book believe me, i’m lying (amazon).
i also love the works of seneca (amazon), cato by joseph addison (amazon), julius caesar by shakespeare, demosthenes (amazon) and the speeches of cicero (amazon).
******
Anyway, you don’t need any more recommendations from me at this point. Start with any of these and you’ll soon be down the rabbit hole. oh, and don’t forget to follow me as i read my life with monthly book recommendations like these, join the other 85,000 subscribers and sign up.
for other lists of my books:
my favorite reads of 2015 my favorite reads of 2014 my favorite reads of 2013 my favorite reads of 2012 my favorite reads of 2011 24 books you’ve never heard of but will change your life a practical philosophy reading list 43 Books About War Every Man Should Read 24 Books To Sharpen Your Strategic Mind 24 Fiction Books That Can Change Your Life 25 Life-Changing Biography Recommendations For The Voracious Reader In You 13 Moral Biographies That Make You A Better Person And Teach You About Life Loving Angels: 36 Books To Help You Finally “Get” The 36 Books Every Wildly Ambitious Young Person Should Read
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