Books Recommended by Ryan Holiday

As a general rule, most new memoirs are mediocre and most business memoirs are even worse. Shoe Dog by Phil Knight is an exception to that rule in every way and as a result, was one of my favorite books of the year and favorite business books ever. I started reading it while on the runway of a flight and figured I’d read a few pages before opening my laptop and working. Instead, my laptop stayed in my bag during the flight and I read almost the entire book in one extended sitting. Ostensibly the memoir of the founder of Nike, it’s really the story of a lost kid trying to find meaning in his life and it ends with him creating a multi-billion dollar company that changes sports forever. I’m not sure if Knight used a ghostwriter (the acknowledgements are unclear) but his personal touches are all over the book—and the book itself is deeply personal and authentic. The afterward is an incredibly moving reflection of a man looking back on his life. I loved this book. It ends just as Nike is starting to turn into the behemoth it would become, so I hold out hope that there may be more books to follow.

I've been a fan of Cal for a long time. His book So Good They Can't Ignore You is one of my favorites, but it's his new book that's probably had the biggest and most immediate impact on me. For those of you who enjoyed Tyler Cowen's Average is Over, you already know how important the ability to focus, be creative, and think at a high level is going to be in the future. This is a book that explains how to cultivate and protect that skill--the ability to do deep work. One thing I've already started doing since reading this book is recording the number of hours of deep work I do each day in my morning journal. It's a way of keeping a running tally and monitoring if I begin to get distracted or slow my pace. Anyway, great book!

It’s unusual for modern biographies to be this good. It’s especially unusually for the subject of the biography to approach the biographer in the way that Steve Jobs did (thinking that he was the intellectual heir of Benjamin Franklin and Albert Einstein). But despite those two things, this bio is and will likely forever be a classic. It shows Jobs at his best–determined, creative, prophetic–and at his worst–petty, selfish, tyrannical and vicious. You can learn just as much about what kind of leader you probably don’t want to be from this book as you can from anything else. That’s what is so strange about Jobs and this biography. You read it and you’re blown away and impressed but I think very few of us think: yeah, I want to be that guy. I want to treat my kids that way, I want to be obsessed with trivial design things that way, I want to hate that way, and so on. You admire him but you also see him as a tragic figure. That’s how you know that Isaacson did an amazing job with this book. TC mark

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”.

I know this will offend many strategy purists, but for most audiences I recommend these two books only with a pretty strong disclaimer. While both are clearly full of strategic wisdom, they are hard to separate from their respective eras and brands of warfare. As budding strategists in business and in life, most of us are really looking for advice that can help us with our own problems. The reality is that Napoleonic warfare does not exactly have its equivalents in today’s society. On the other hand, Sun-Tzu is so aphoristic that it’s hard to say what is concrete advice and what is just common sense. But the books are so convincing that you might still end up leaving thinking that they can be easily applied. So, again, check these books out if you’re really interested, but I think some of the other books are much better places to start.

This book is out on Tuesday and it's also very good. An atomic habit is a tiny habit or change that can have an enormous impact on your life. Getting up a little earlier, deleting social media from your phone, automating your savings, developing a system, these are atomic habits. Me personally, I don't feel like I am particularly talented or even that disciplined, but I have a number of atomic habits that I started early on that have had a massive compounding benefit. My blurb of this one: "A special book that will change how you approach your day and live your life."

Part of ambition is modeling yourself after those you’d like to be like. Austin’s philosophy of ruthlessly stealing and remixing the greats might sound appalling at first but it is actually the essence of art. You learn by stealing, you become creative by stealing, you push yourself to be better by working with these materials. Austin is a fantastic artist, but most importantly he communicates the essence of writing and creating art better than anyone else I can think of. It is a manifesto for any young, creative person looking to make his mark. Pair up with Show Your Work which is also excellent.

Now this one is certainly a little less historical than the others, if only because most of the profiles are about companies founded in the last ten years. Written by Jessica Livingston, a founder of YCombinator, the book profiles some of the hottest and most successful startups in Silicon Valley history. It shows how the founders manage to create massive growth, usually with very few resources. Now I’m not saying that companies like Hot or Not compare with the accomplishments of Pericles or Da Vinci, but you can certainly see how this book captures a moment in time—and its leading men and women—and what that means. This is the most current book on the list (besides mine) but I think many of you will like it. Plus you can learn a lot about the tech scene in one swoop.

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.

Of course, this is a must read. Machiavelli is one of those figures and writers who is tragically overrated and underrated at the same time. Unfortunately that means that many people who read him miss the point and other people avoid him and miss out altogether. Take Machiavelli slow, and really read him. Also understand the man behind the book–not just as a masterful writer but a man who withstood heinous torture and exile with barely a whimper.

Machiavelli is a glimpse into a time when power was literal and out for public viewing–when he talks about making an example of someone, he doesn’t mean calling them out, he means putting their head on a pike. Don’t let that scare you because we’re not as far from that world as we’d like to think. Deny that at your own peril.

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.

Part of ambition is modeling yourself after those you’d like to be like. Austin’s philosophy of ruthlessly stealing and remixing the greats might sound appalling at first but it is actually the essence of art. You learn by stealing, you become creative by stealing, you push yourself to be better by working with these materials. Austin is a fantastic artist, but most importantly he communicates the essence of writing and creating art better than anyone else I can think of. It is a manifesto for any young, creative person looking to make his mark. Pair up with Show Your Work which is also excellent.

A biography has to be really good to make read you all 800 pages. To me, this was one of those books. Since reading it earlier this year, I’ve since found out it is the favorite book of a lot of people I respect. I think something about the quality of the writing and the empathic understanding of the writer that the main lessons you would take away from someone like Rockefeller would not be business, but life lessons. In fact, when I went back through and took notes on this book, I filled out more cards for Stoicism than I did for Strategy, Business or Money. 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. Rockefeller did neither of these things, he grew more open-minded the older he became, more generous, more pious, more dedicated to making a difference. Does that excuse the “awful” things that he did? Well, the things he did really weren’t that awful so yes. (By that I mean I’d certainly choose him over the robber barons of this age like Zuckerberg or Murdoch.)

The unassuming Georgetown computer science professor has become one of this generation’s leading voices on how we can all work more wisely and more deeply. With media consumption continuing to go way up (which, for most of us, means happiness and productivity continue to go way down) and the world becoming noisier every day, this book is an urgent call to action for anyone serious about being in command of their own life. The minimalism movement successfully led millions to opt out of the many possessions we’re told we’re supposed to crave and focus instead on the small number of things that bring the most meaning and value to our lives. The same ideology applies to our online lives. Digital clutter is stressful. We don’t need the constant connectivity, the pages and pages of apps, the incessant scrolling and clicking. New technologies can improve our lives if we know how to best leverage them. This book already helped me break my Facebook addiction—and the first month of the year has been a big improvement for me because of that.

This might feel like a weird book to include, but I think it presents another side of strategy that is too often forgotten. It’s not always about bold actors and strategic thrusts. Sometimes strategy is about subtle influence. Sometimes it is framing and small tweaks that change behavior. We can have big aims, but get there with little moves. This book has excellent examples of that kind of thinking and how it is changing politics, government and business. My favorite example is about the bumblebee that they started putting on urinals–which drastically reduced the amount of spray and spillage because it changed where men aimed when they peed. It’s not exactly the coolest strategy but it solved a problem. So we can learn from it.

It was wonderful to read these two provocative books of essays by two incredibly wise and compassionate women. [...] 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 this year.

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).

Widely held as a classic, this book is much more than a manifesto and manual on swordsmanship and martial arts. It’s about the mindset, the discipline, and the perception necessary to win in life or death situations. As a swordsman, Musashi fought mostly by himself, for himself. His wisdom, therefore, is mostly internal. He tells you how to out-think and out-move your enemies. He tells you how to fend for yourself and live by a code. And isn’t that precisely what so many of us need help with every day?

In 2014, 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. Out of all the books I read this year, I marked this one up the most. 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 made an effort to read some classical poets and playwrights this year. The Aneiad 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.

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.

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 belabor the point: read this book. Thank me later. [...] Both will make you think and both made me a better person this year.

These are two very short books but will help you understand the topics more than thousands of pages on the same topic by countless other writers. In my view, Hart is unquestionably the best writer on military strategy and history. Better than von Clausewitz, that’s for sure (who for all the talk is basically useless unless you are planning on fighting Napoleon). His theories on the indirect approach is life changing, whether you’re struggling with a business or just office politics. I can’t say much more than read these books. It’s a must.

I’m not sure what compelled me to pick Fahrenheit 451 back up but I’m so glad I did because I was able to see the book in a very different context. Bradbury’s message (made explicit in his 50th Anniversary Afterword) is much less a warning against government control and much more about a road to hell paved by people attempting to rid the world of offensive speech and conflicting ideas. In a world of microaggressions and outrage porn, this is an important idea to see in such a timeless work of fiction.

For me, this year was filled with what one might called “cautionary biographies”—bios of people you don’t want to end up like—and Hughes is at the top of the list. The authors clearly respect what was great about Howard—his daring, his talent for flying, his sense for people and love of negotiation—but they also see clearly his many, crippling flaws. They are able to tell his story in a way that gives one real insight into the life of a tragic and tortured figure. I very much related to the stories in the book given my more recent experiences at American Apparel and I imagine anyone else who has dealt with powerful personalities and eccentric figures will too.

A dark and moving first-person narrative, about the conflicting drives for self-preservation and self-immolation inside all of us. Hunger is about a writer who is starving himself. He cannot write because he is starving and cannot eat because writing is how he makes his living. It’s a vicious cycle and the book is a first-person descent into it. Strangely modern for being published in 1890 and ultimately inspired a lot of great stream-of-consciousness writing since (but influence goes unacknowledged because Knut was a Nazi sympathizer).

Wow, did you know that Moby Dick was based on a true story? There was a real whaling ship that was broken in half by an angry sperm whale. But it gets even more insane. The members of the crew escaped in three lifeboats, traveling thousands of miles at sea with little food and water until they slowly resorted to cannibalism(!) Besides being an utterly unbelievable story, this book also gives a great history into the whaling industry and the cowboys/entrepreneurs who led it. Definitely recommend and I promise my spoilers did not ruin anything.

After Marcus Aurelius, this is one of my favorite 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.

I know this will offend many strategy purists, but for most audiences I recommend these two books only with a pretty strong disclaimer. While both are clearly full of strategic wisdom, they are hard to separate from their respective eras and brands of warfare. As budding strategists in business and in life, most of us are really looking for advice that can help us with our own problems. The reality is that Napoleonic warfare does not exactly have its equivalents in today’s society. On the other hand, Sun-Tzu is so aphoristic that it’s hard to say what is concrete advice and what is just common sense. But the books are so convincing that you might still end up leaving thinking that they can be easily applied. So, again, check these books out if you’re really interested, but I think some of the other books are much better places to start.

This was someone I knew little about before the year began, and by the end of it found myself referencing and thinking of him constantly. It is equal parts due to the greatest 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—so if you are going to read one biography this year, read Sherman: Solider, Realist, American.

There’s no question this was the year’s best book about media and culture–maybe even the best of the decade. Not only is it provocative and insightful, but the idea—interviewing and focusing on people who have screwed up and found themselves in the midst of massive online controversies—is one I am genuinely jealous of. Ronson proceeds to write about it with such sensitivity, empathy, humor and insight that I was blown away. If you’ve at all appreciated any of my media criticism over the years, please read this book. It looks at all that’s wrong with the rage and glee with which we tear people down–often people who were never public figures to begin with. He is just a helluva writer. If you get a chance, watch Monica Lewinsky’s TED talk which is also surprisingly good and pairs well with the ideas in the book.

I forget who said it but I heard someone say that Catcher in the Rye was to young white boys what the Autobiography of Malcolm X was to young black boys. Personally, I prefer that latter over the former. I would much rather read about and emulate a man who is born into adversity and pain, struggles with criminality, does prison time, teaches himself to read through the dictionary, finds religion and then becomes an activist for Civil Rights before being gunned down by his former supporters when he tempers the hate and anger that had long defined parts of his message.

This was definitely the best business/leadership book I read this year. It proves that we have really missed what makes great teams and organizations work. It’s not star players, it’s not even how much they can spend–it’s whether they have great captains. Walker’s chapter on “carrying the water” had some great insights re: Ego is the Enemy and I think this incredibly well-written book should be studied by anyone trying to build a great organization (or trying to find a role for themselves inside one).

I thought I’d read this book before but clearly they gave me some sort of children’s version. Because the one I’d read as a kid wasn’t a 1,200 page epic of some of the most brilliant, beautiful and complicated storytelling ever put to paper. What a book! When I typed out my notes (and quotes) after finishing this book, it ran some 3,000 words. I was riveted from cover to cover. I enjoyed all the stuff I missed as a kid: the Counts struggle with his faith in light of what was done to him, the Hundred Days of Napoleon’s return, his rants against technology, the criticism of newspapers, the influence of ancient philosophy, ultimately, a warning against being consumed by revenge. Please—if you’re going on a long trip or looking to check out of modern events for a while—get this book. I recommend the Penguin Classics edition.

The book sucked me in completely. The subject, Samuel Zemurray, is fascinating and compelling. The writer has a voice that is utterly unique. Since reading this book, I have explored all of this further: I studied Zemurray (whose house was not far from mine in New Orleans and still stands) and am using his story in my next book. I interviewed the author, Rich Cohen. And I read his other books, am particularly found of Tough Jews: Fathers, Sons and Gangster Dreams. The book has all sorts of things going for it: it’s the American Dream, it’s history via microcosm, it’s drama/violence/intrique, and it’s a course in business strategy and leadership. Everyone I have recommended it to was blown away. I won’t say it’s as good as The Tiger, which was my favorite book of 2011, but in terms of an author I’d never heard of taking a subject I don’t care about and making it AWESOME? This book deserves to be talked about in the same breath.

This is an incredible book by an incredible author (his Rising Tide I read many years ago and loved). "It was only influenza, it's only influenza," Barry says over and over again. Because that's what people were saying in 1918 as millions of people died, as the US and the world wrestled with an overwhelming pandemic for which they were not prepared. Cities held parades despite the warnings, people insisted on going to church, they declined to wear masks, they told themselves it was a hoax. History repeats itself, and we make the same mistakes over and over again, don't we? The book drags a little at the beginning but once it gets going, it'll sober you up and humble you real fast. In 2005, George W. Bush read this book, spoke with the author and instituted some basic pandemic preparations (not an illiterate leader—in fact, Bush was an underrated reader). And then most of these plans were forgotten about or dismantled and we told ourselves once again, it's only the flu, it's only the flu.

Robert has been writing this book since Mastery came out in 2013 and it shows - it's a spectacular masterwork that builds atop all his other books. Robert's book have always been an unvarnished look at how the world really works, for better and for worse. What I like about this book is that it pushes us to question our own biases, our own assumptions, irrationalities and tendencies. It's almost as if we believe other people have a 'human nature' but we don't - we're logical, fair, motivated by higher purposes always. Of course this is silly. Lots of good stuff here for anyone in a position of leadership, who works with an audience or studies human behavior.

When I was younger I would ask any smart or successful person I met to recommend a book for me to read. Dr. Drew recommended that I read The Rise of Theodore Roosevelt. It immediately became a lifetime favorite that I have reread several times (Amazon tells me I bought it Oct 26, 2006). It ends the day he is telegraphed that McKinley has been assassinated–so the book focuses on everything before that from his unusual childhood and struggle with asthma to his love nature to his trip west after the simultaneous death of his wife and mother. I’m not sure why I took so long to read this sequel but it is just as good, if not better. Focusing on Roosevelt from the end of presidency to the end of his life, there is enough material just in that portion of his life to put everyone else to shame. It covers his retirement, his safari in Africa, his exploration of the River of Doubt, his run as a third party candidate and finally his heartbreaking struggles with WWI and his son’s death. Goddamn, TR was a good man.

I was heartily recommend this book by Dr. Drew and since the last book he recommended changed my life as a young man, I did not hesitate to get it. Now this is a tough book, a really tough book, but it is amazing. People think of Adam Smith as being this ruthless economist who studied self-interest but this forgotten book reveals that he was in fact, a great moral and practical philosopher. It is clear to me that Smith was profoundly influenced by the Stoics and by the great classic thinkers of history. Intimidated? Well, good news! It turns out Penguin published a new book this year called How Adam Smith Can Change Your Life by Russ Roberts and it happens to be an eminently accessible access point into Theory of Moral Sentiments. (In fact, I liked both so much, I am buying copies to send as a package to a handful of close friends) I hope you pick up either book and I hope its deep thoughts on the pursuit of fame, of money, and of course, his concept of the “indifferent spectator” to guide your actions, make you think as much as they did for me.

These two books are the two best books of political thinking and theater from both the left and the right. Regardless of ideologies, both are experts in influencing and leading public perception through image and words. It actually matters whether we’re talking about illegal immigrants or undocumented workers, or whether we describe the problem as climate change or global warming. Strategists need to understand the power of language and framing–it doesn’t matter how right you are, if you lose this battle it can be impossible to rally people to your cause. Read both these books.

It’s basically a collection of Tolstoy’s favorite passages from the ancient and classic texts, with excellent supplements from his own considerable wisdom. Each day draws on Chinese, Jewish, Stoic, Christian, Indian and Arabic sources (he quotes everyone from Emerson to Marcus Aurelius to Lao-Tzu) and manages to give good, actionable advice from all of these differing schools. It’s no wonder the Communists banned and suppressed this book, because it challenges everything they were trying to deny about human nature and the human experience. This book should be much, much, more popular and I promise your mornings will be improved if you start them with it.

It’s hard for me to recommend just one great biography this year, so I won’t even try. I’ll just start with this biography of John Hay, which was my favorite–though there were many close seconds. John Hay started as a teenage legal assistant in the law office of Abraham Lincoln. He ended his career as the Secretary of State for William McKinley and Theodore Roosevelt. How nuts is that? You can basically understand the entire period of American history from the Civil War through WWI through one man who saw it all. Great biography of politics, the press, and American society.

In 1934, William Seabrook was one of the most famous journalists in the world. He was also an alcoholic. But there was no treatment for his disease. So he checked himself into an insane asylum. There, from the perspective of a travel writer, he described his own journey through this strange and foreign place. Today, you can’t read a page in the book without seeing him bump, unknowingly, into the basic principles of 12-step groups and then thwarted by well meaning doctors (like the one who decides he’s cured and can start drinking again). On a regular basis, he says things so clear, so self-aware that you’re stunned an addict could have written it–shocked that this book isn’t a classic American text. Yet all his books are out of print and hard to find. Two of my copies are first editions from 1931 and 1942. It breaks your heart to know that just a few years or decades later, his options (and outcome) would have been so very different (he eventually died of an opium overdose).

This was the most important book I read this year. It’s the only one I framed a passage from to put on my wall. It was the only one I thought was so good I bought for multiple other people this year (it also inspired the one piece of writing I am most proud of this year). 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.

I don’t think there was anyone in the 1920s who would have believed that this book would be completely forgotten. By all accounts, it was destined to be a classic critical novel of the American Dream. You can’t read anything about the ’20s and ’30s that doesn’t comment on Babbitt (sold 130,000 copies its first year, HL Mencken loved it, it won Lewis a Nobel Prize). Calling someone a “Babbitt” was considered an insult and the phrase became a constant topic of conversation in the media and literature.

Yet, here we are 80-90 years later: you’ve probably never heard of the term or the book. Perhaps it’s because the biting satire of American suburban middle class life cuts deeper now than it did then. It doesn’t matter if the book is old, it’s still very funny and at its core, a critique of conformity and what Thoreau called the “life of quiet desperation.

I am putting this book on here as a cautionary tale for all the supposed business strategists out there. Because it turns out that most (if not all) genius business strategies are totally misguided and lead to catastrophic failure. Your planned merger, roll up, pivot–it’s probably got glaring strategic flaws in it. Why? Because you’re too caught up in your own vision to see what can go wrong, to see where you’ve been overly optimistic, to accept how little you control. Pairing this book with some of the books on war is a good idea. It will humble you and keep you conservative–which all good strategists are. “Boldness” should be used sparingly because it’s often actually just stupidity in disguise.

Written in 1949 by the famous journalist John Gunther about his death of his son–a genius–at 17 from a brain tumor, this book is deeply moving and profound. Every young person will be awed by this young boy who knows he will die too soon and struggles to do it with dignity and purpose. Midway through the book, Johnny writes what he calls the Unbeliever’s Prayer. It’s good enough to be from Epictetus or Montaigne–and he was fucking 16 when he wrote it. It’s reading the book for that alone.

These two books are the two best books of political thinking and theater from both the left and the right. Regardless of ideologies, both are experts in influencing and leading public perception through image and words. It actually matters whether we’re talking about illegal immigrants or undocumented workers, or whether we describe the problem as climate change or global warming. Strategists need to understand the power of language and framing–it doesn’t matter how right you are, if you lose this battle it can be impossible to rally people to your cause. Read both these books.

Older biographies are better in my experience. This one is 50+ years old and that’s right in the sweet spot. It didn’t have to be trendy, it didn’t have to psychoanalyze, it didn’t have to be political correct or controversial. It just had to be a sweeping, conclusive picture of the man. Modern enough to be historically accurate, old enough to still have respect for ambition. No question, this is a big book but I learned a lot. For instance, I had no idea that Edison had been mostly deaf (and that that deafness fueled and improved many of his sound inventions). I didn’t know about his friendship with Henry Ford or what a shrewd businessman Edison was. If you like big biographies, read this.

The prospects Eleanor Roosevelt faced when she entered the White House were not good. First Ladies hadn’t done anything in decades besides party planning and a few of her predecessors had had nervous breakdowns. She wanted to do something different. This is a book about her political and social acumen–her ability to turn a meaningless position into a powerful platform for change and influence. I read this book and came away so impressed. We can learn a lot.

The prospects Eleanor Roosevelt faced when she entered the White House were not good. First Ladies hadn’t done anything in decades besides party planning and a few of her predecessors had had nervous breakdowns. She wanted to do something different. This is a book about her political and social acumen–her ability to turn a meaningless position into a powerful platform for change and influence. I read this book and came away so impressed. We can learn a lot.

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.”

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.”

This a novel from the writer of True Detective (from before he was the guy from True Detective). Guess what? It's really really good. It's a dark noir story (surprise!) but it's got a great character and great lines...even a touching ending. Also, and I know this is pretty controversial, but I think the second season of True Detective was pretty damn good.

This book – of a long forgotten war – really functions as a biography and strategic analysis of some of the greatest minds in the history of war. We have Pericles, Brasidas, Alcibiades and many others. The anecdotes and the stories in this book are timeless. If you make your way all the way through it, I promise you will not forget it. Because the war was so long, involved so many different countries and was so varied (sea, land, siege, politics), it basically covers every type of situation you can think of. Think of this book as a textbook. Read it.

Written in 1901 these are uplifting business oriented biographies of men like Marshall Field, John D Rockefeller, Alexander Graham Bell and Thomas Edison and women like Helen Gould and Julia Ward Howe (creator of Battle Hymn of the Republic). I was referred this book by Maria Popova over at Brainpickings and loved it—I’ve referred to it many times since reading it.

Hurricane Carter’s biography is about a man who refused to be anything but himself—even in prison. There are great parallels to his personal struggles to maintain the sovereignty of self amidst awful circumstances and the lessons of Stoicism. My favorite: how he refused to sue the government after his wrongful conviction was overturned because it’d be saying that they’d taken something from him, that he was still dependent on them which even after decades in prison he refused to resign himself to accepting.

It’s going to feel weird reading a book about a German general in WWII but for Rommel we must make an exception. Yes, he fought for a terrible cause. But he did so brilliantly — as a soldier, strategist, and leader. His victories in North Africa were the stuff of legend, and had the US and British troops not ultimately had better resources, the whole thing might have turned out very differently. You cannot read about Rommel and not like and admire the man. I’m saying this so you’ll be prepared and ready to remind yourself that that doesn’t excuse his actions. But you can still learn from him.

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.

Ironically, Diogenes’ most famous biography in this collection is of the other Diogenes—Diogenes the Cynic. Other excellent and illustrative sketches include Zeno, Ariston, Cleanthes and Chrysippus the Stoic. Heraclitus is another great biography. All of these vary in length. Zeno is over a 150 pages, Herillus (not to be confused with Heraclitus) is 2 pages. But regardless of length, they are all quite good. My favorite little quirk of the book is Diogenes’ weird poem that he writes about each philosopher and of course the credulity with which he reports on their unusual deaths.

Written by an anonymous author (possibly multiple) in the 4th century, these biographies are a mix of myth, legend and fact about some of the most powerful men who ever lived: the Roman emperors. We have Hadrian, Marcus Aurelius, Trajan, Avidius Cassius, Severus and countless others. I’m sure you can guess my favorite subject. Also try The Twelve Caesars by Suetonius Translated by the peerless Robert Graves, these are more biographies of the Roman emperors—from Julius Ceasar to Domitian.

Now if you’re looking for some inspiration and excitement, Magellan is the book for you. What makes a man an explorer? What made Magellan so he could find a passage he had no reason to be certain he could find? And how thankless a job! [...] There are some books where you feel like everything the writer did led up to this masterpiece they were born to create: that might be what this book is. It’s just perfect in every sense. Cannot recommend highly enough.

A man is born a slave. Man teaches himself to read. Man decides he will no longer consent to being whipped, realizes that slavery is dependent on this consent and then leaves it. In fact, his self-education was so complete that he went on to become one of America’s foremost intellectuals. That is the life of Frederick Douglass. You need to read it.

This is the lost and translated book that came out of a series of pieces Johnson–perhaps the greatest boxer who ever lived–wrote for a French newspaper in 1911. It’s not very long but it is full of really interesting strategies and anecdotes. You get the sense that he was an incredibly intelligent and sensitive man–clearly had a thirst for drama and attention. Who knows what place he would occupy in our culture and history had he not been taken down so thoroughly by racism and genuinely evil people? But despite all that, he was always smiling. As Jack London put it after Johnson’s most famous fight: “No one understands him, this man who smiles. Well, the story of the fight is the story of a smile. If ever a man won by nothing more fatiguing than a smile, Johnson won today.”

John Dillinger was played by Johnny Depp. Most people know who he was–mostly because he died in a hail of bullets. But they forget that the other Public Enemy #1 at the time was Alvin Karpis and he didn’t die. In fact, he lived up until the 1980s. Just enough time to do a couple decades at Alcatraz with guys like Al Capone. During a temporary transfer to an alternate prison, Karpis met a young weirdo named Charlie Manson and taught him how to play guitar.

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.

Written by President Kennedy when he was bedridden after back surgery, Profiles in Courage recounts the inspiring acts of eight different American Senators, including John Quincy Adams, Daniel Webster, Sam Houston, and Robert A. Taft. Kennedy had recently been elected as the junior Senator from Massachusetts and was inspired to write a book after reading a passage from The Price of Union about an act of courage by John Quincy Adams while serving in the Senate. It was heartening to read about Senators willing to cross party lines and stand up for their principles given the current state of our Congress.

I'd never read any of Seneca's plays before, which was a big gaping hole in my knowledge. During his lifetime, Seneca was actually more famous for his tragedies than he was for his philosophy (there is a line from one of his plays entombed as graffiti at Pompeii). Anyway, I was enthralled by these dark, disturbing but ultimately stoic plays. My favorite line comes from Hercules: "I do not ask you to show the path; just to give permission, father, I shall find the way." And related to that, my friend Tim Ferriss has released an amazing audiobook edition of Seneca's Letters. You must check them out.

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 behaviors and strengths so it would only make sense that they would have developed into two very different entities.

I went so deep into Civil War in 2012 that I lost track of all the books. I started this last year when I read Sherman by B.H Liddell Hart (and recommended as a favorite). I came to admire Sherman so deeply that I read two more books about him. I came to admire Sherman so deeply that I read two more books about him: Sherman’s Memoirs and a big old book from 1933 Sherman: Fighting Prophet.

Ah yes, the drive that we all have to be better, bigger, have more, be more. Ambition is a good thing, but it’s also a source of great anxiety and frustration. In this book, philosopher Alain de Botton studies the downsides of the desire to “be somebody” in this world. How do you manage ambition? How do you manage envy? How do you avoid the traps that so many other people fall into? This book is a good introduction into the philosophy and psychology of just that.

These are two very short books but will help you understand the topics more than thousands of pages on the same topic by countless other writers. In my view, Hart is unquestionably the best writer on military strategy and history. Better than von Clausewitz, that’s for sure (who for all the talk is basically useless unless you are planning on fighting Napoleon). His theories on the indirect approach is life changing, whether you’re struggling with a business or just office politics. I can’t say much more than read these books. It’s a must.

I'll put here what I emailed Malcolm when I finished the book: "Just finished your new book in one sitting yesterday. So good. You are at the height of your powers and remain an inspiration to all of us trying to master an un-masterable profession." It's a little less practical or self-improvement oriented than his previous books, but far more thought provoking.

What a book. It’s not as good as What Makes Sammy Run but 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?

If you like Asylum, read The Crack Up, a book put together by Fitzgerald’s friend Edmund Wilson after his death. It is such an honest and self-aware compilation of someone hell-bent on their own destruction. At the same time, Fitzgerald’s notes and story ideas within the book make it undeniably clear what a genius he truly was. It’s a sad and moving but necessary read.

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

I read The Gift of Failure: How the Best Parents Learn to Let Go So Their Children Can Succeed by Jessica Lahey because I have a son, but it’s worth reading for anyone, parent or not. Written by a middle school teacher and education expert, the book is an exploration of how one raises self-sufficient children who are responsible for themselves.

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.

One of my favorite books I read last year (sneaked in under the wire). The author is so passionate, her history of this magnificent animal is so sweeping and captivating, her language is so beautiful. It's just great. Plus, I learned a lot. For instance, I had no idea that there is almost no violence depicted in cave paintings (I ended up chatting about it on Ask Historians, one of my favorite places on the internet) or that a lot of archaeologists think that horses originated in North America, migrated to Europe, went extinct here and then traveled back. In this way, horses were our gift to Europe...which they gifted back to us. I wish there'd been a bit more anthrozoology in the book--there's very little discussion of the role of the horse in history over the last 200-300 years (the most interesting part), but perhaps that's for a second book.

After the Caro series, I started William Manchester’s equally epic three volume set on Winston Churchill (Visions of Glory, Alone, Defender of the Realm) which Robert Greene gave me as a wedding present last year. Like all truly great long reads, you learn not just about the subject but every intersecting one: the history of British peerage, the Victorian era, the British Empire, Colonialism, modern warfare, international relations, evil, the nature of genius, the effects of absent parents. The book is masterfully written about a masterful man—Churchill was a soldier, a writer, a politician, a statesman, a strategist and a true great man of history. Each book in the series is equally distinct and interesting. The first is Churchill as a young, ambitious man. The second is his time in the political wilderness, when his ego has driven him from power and into writing and thinking. The third is his time back on the world’s stage, in what was perhaps the finest hour of any empire in any era. The last book is probably the best. It features the famous bulldog version of Churchill: rescuing the troops at Dunkirk, persevering through the Blitz, vowing to fight on the landing grounds and the beaches and in the streets, whatever the cost may be. The sheer determination of this man, to take an entire country on your back and defy a horde which had overrun the European continent in a matter of months…it’s almost breathtaking to think about.

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.

Patriotism is not a concept that gets a lot of love today. But this essay/book makes you think a little. Released in 1863 during the height of the Civil War, the plot’s simple: an innocent man caught up in Aaron Burr’s treasonous conspiracy stands trial for his actions. When asked to address the judge, he bitterly remarks that he wishes to be done with the United States forever. So the judge grants his wish as a punishment–he’s sentenced to live the rest of his life in a cabin aboard ships in the US Navy’s foreign fleet, and no sailor is to ever mention the US to him again. He dies many years later, an old man like Rip Van Winkle, unsure of the changing world around him. For those with some understanding of historical, you’ll enjoy the meta-fiction of it, for those that haven’t it is still a very good look into early America.

The daily notes of a strong but dying woman (born 1883, written in 1968) watching her life slowly leave her and wind to a close. The wisdom in this thing is amazing and the fact that most people have no idea exists–and basically wait until the end of their life to start thinking about all this is very sad to me. Also I love her generation–alive during the time of Wyatt Earp yet lived to see man land on the moon. What an insane period of history.

I went so deep into Civil War in 2012 that I lost track of all the books. I started this last year when I read Sherman by B.H Liddell Hart (and recommended as a favorite). I came to admire Sherman so deeply that I read two more books about him. I came to admire Sherman so deeply that I read two more books about him: Sherman’s Memoirs and a big old book from 1933 Sherman: Fighting Prophet.

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.

I read my first Robert Caro book, The Power Broker, almost ten years ago. Reading this one--his most recent--on the ascension of Lyndon Johnson reminded me just how much I LOVE really long books (I even ended up writing an article about them). As always, Robert Caro is a master of his craft. Despite being some 768 pages, this book flies by and you learn something about history, about human nature, about power on almost every page. I'll be moving on to one of his other Lyndon Johnson books next.

I've been meaning to read this book for a while, and after I did I bought copies for everyone at my company (since we produce books and other kinds of content). In the book, Seabrook explains how just a few men and women are responsible for producing nearly every hit song you hear on the radio, see on YouTube or listen to on Spotify. He explains the economics of the music industry in a way that allows you to understand why music is the way that is today (the good parts and the bad parts). As someone who tends to listen to songs on repeat while I write--usually bad songs--it was interesting to hear how many of them were made. My only gripe: He neglects a couple people I would have liked to hear more about like Sia and Linda Perry who are just as prolific as Dr. Luke and Max Martin.

I don’t have a lot of modern books on this list, but this is an excellent one. We tend to wrongly think that strategy is about coming up with a genius plan and then committing to it. In fact, this is often a recipe for disaster, particularly in business. Though success often requires a total investment in a particular strategy, this is also the recipe for extreme failure. It’s a paradox. Michael Raynor’s book has important thoughts on this inherent paradox as well as approaches for mitigating and avoiding it.

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.

You may have heard about the story on the internet a while back: 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. The autopsy later revealed that the tiger had been shot something like a dozen times during its life and lived. The story is very similar to that of the Tsavo maneaters, which was turned into the underrated Val Kilmer movie The Ghost and the Darkness.

There are all sorts of well-selected threads from evolutionary psychology and biology in this book and it makes the book a self-educator’s dream. You can pick and choose which ones you want to follow next–trusting safely that the author has pointed you in an interesting and valuable direction. But that’s just the meta-stuff that is a bonus with this book, and it’s worth pointing out only because the rest of the book is just so fucking interesting and exciting.

I read this book (note: The Gift of Failure) not long after reading Senator Sasse’s The Vanishing American Adult and found it to be a great companion. We forget that homework doesn’t matter, grades don’t matter—only what the process they represent matters. Children are not a reflection of their parents, they depend on their parents to raise them into adults who can be reflections of who they uniquely are.

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…

There are lots of books on aspiring to something. Very little are from actual people who aspired, achieved, and lost it. With each and every successful move that he made, Jim Paul, who made it to Governor of the Chicago Mercantile Exchange, was convinced that he was special, different, and exempt from the rules. Once the markets turned against his trades, he lost it all — his fortune, job, and reputation. That’s what makes this book a critical part in understanding how letting arrogance and pride get to your head is the beginning of your unraveling. Learn from stories like this instead of by your own trial and error. Think about that next time you believe you have it all figured out. (Tim Ferriss recently produced the audiobook version of this, which I recommend.)

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.

Xenophon, like Plato, was a student of Socrates. For whatever reason, his work is not nearly as famous, even though it is far more applicable. Unlike Plato, Xenophon studied people. His greatest book is about the latter, it’s the best biography written of Cyrus the Great (aka the father of human rights). There are so many great lessons in here and I wish more people would read it. Machiavelli learned them, as this book inspired The Prince.