Ryan Holiday’s 2014 Reading List

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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 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.

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.

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

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.