A few months ago, Chief Medicine Crow, one of the last remaining links to the Native American tribes of the Wild West died at age 102. He had grown up hearing stories about George Armstrong Custer from his grandfather, who’d been a scout for the doomed general at Little Bighorn in 1876. A soldier himself in the Second World War, Medicine Crow was one of the last Crow people to ever accomplish the four deeds required to be considering a war chief (command a war party, steal an enemy horse, touch an enemy without killing him and taking an enemy’s weapon).

He was a fascinating man, not just for what he did but also for what he represents to us now. He was, to use a phrase coined by Jason Kottke, a “human wormhole.” His unusual and long live is a reminder to how connected the past and present really are.

A curator at the Smithsonian described meeting Medicine Crow as “you’re shaking hands with the 19th century.” Which an amazing concept. A few intrepid historians on reddit recently discovered an even more amazing one, calculating that it would take a chain of just six individuals who shook hands with one another to connect Barack Obama to George Washington across the centuries (Obama ->Queen Elizabeth II -> Herbert Hoover -> William H. Taft -> Benjamin Harrison -> William Henry Harrison -> Benjamin Harrison V -> George Washington).

I’ve become fascinated with discovering and tracking some of these reminders. For some time now, I’ve kept a file of them on 4×6 notecards in my house. My friends and I email these moments to each other as we find them — some absurd (Oscar Wilde and Walt Whitman may have hooked up), coincidental (Orson Welles claimed to have been in the Biograph Theater in Chicago where John Dillinger was killed by the FBI) and some that are so unbelievable that they might just blow your mind (there’s a video from a 1956 CBS game show, “I’ve Got a Secret,” with a very old guest whose secret was that he was in Ford’s Theatre when Lincoln was assassinated. Appearing with him on the show? Lucille Ball.)

Here in modern life, it’s easy to think the past is dead and distant, until we bump up against the reality of Faulkner’s admonition that it’s not really even past. England’s government only recently paid off debts it incurred as far back as 1720 from events like the South Sea Bubble, the Napoleonic wars, the empire’s abolition of slavery, and the Irish potato famine — meaning that for more than a decade and a half of the twenty first century there was still a direct and daily connection to the eighteenth and nineteenth centuries. (The US is still paying pensions related to both the Civil War and the Spanish-American War.)

I’ll share a few more wormholes before I get to my point — because I promise there is more to this than just strange trivia.

Did you know that Tom Pratt, a football coach whose team the Arizona Cardinals narrowly missed going to the Super Bowl in 2015, was also on the coaching staff for the Kansas City Chiefs in the very first Super Bowl fifty years ago? Or that there are whales alive today who were born before Melville published Moby Dick? Or the world’s oldest tortoise, Jonathan, lives on an island in the Atlantic and is 183 years old? Or that President John Tyler, born in 1790, who took office just ten years after little Jonathan was born, still has living grandchildren?

War is perhaps the strangest source of these anomalies. Did you know that Winston Churchill and James Bond creator Ian Fleming’s father fought in the same unit in WWI? When Fleming’s father was killed, Churchill wrote his obituary. General Simon Bolivar Buckner was a Confederate general in the Civil War (he surrendered to Grant at Fort Donelson). His son Simon Bolivar Buckner Jr also became a General, and he died at Okinawa some 83 years later. General MacArthur — his father, Arthur MacArthur, Jr. — was a Civil War hero for the Union. Stonewall Jackson had a granddaughter who lived to be 104. She died in 1991.

In high school, a promising young student at the Virginia Military Institute named George Marshall petitioned the president for a military commission. Which President did the creator of the Marshall plan petition? William McKinley (just months before man’s life was cut short by an assassin’s bullet.) And most unbelievably, what of the fact that Robert Todd Lincoln was present as his father died of assassination, was at the train station with President James Garfield was assassinated, and was in attendance at the event in which McKinley was assassinated? Three assassinations, spread out over 40 years. Robert Todd Lincoln himself lived to be 82, dying in 1926. He could have read stories published by F. Scott Fitzgerald. He drove in a car. He talked on the telephone. He would have heard jazz music.

And these are just the events of the so called modern history.

We forget that woolly mammoths walked the earth while the pyramids were being built. We don’t realize that Cleopatra lived closer to our time than she did to the construction of those famous pyramids that marked her kingdom. We forget that Ovid and Jesus were alive at the same time. When British workers excavated the land in Trafalgar Square to build Nelson’s Column and its famous bronze lions, in the ground they found the bones of actual lions, who’d roamed that exact spot just a few thousand years before.

The effect of these stories — after the novelty wears off — is an intense humbling. We like to think that we are special — that we live in blessed, unprecedented times. It’s this self-absorption that disconnects us from the universe we belong to. It’s unthinking ego that makes us assume that because the photos of the past were in black and white, that the past itself was too.

Obviously, it wasn’t — their sky was the same color as ours (in some places brighter than ours), they bled the same way we did, and their cheeks got flushed just like ours do. “Think by way of example on the times of Vespasian,” wrote the wise Marcus Aurelius some 1900 years ago, “and you’ll see all these things: marrying, raising children, falling ill, dying, wars, holiday feasts, commerce, farming, flattering, pretending, suspecting, scheming, praying that others die, grumbling over one’s lot, falling in love, amassing fortunes, lusting after office and power. Now that life of theirs is dead and gone… the times of Trajan, again the same… ”

Again the same for us now. However much we celebrate our own exceptionalism.

In Goethe’s The Sorrows of Young Werther (which was a favorite of Napoleon’s) there is a scene in which Werther writes to a friend about his daily trip to a small, beautiful spring. He sees the young girls coming to gather water and thinks about how many generations have been doing that — have come and had same thoughts he is having. “When I sit there the patriarchal ways come vividly to life about me,” he says, “and I see them all, the ancestral fathers, making friends and courting by the spring, I sense the benevolent spirits that watch over springs and wells. Oh, anyone who cannot share this feeling must never have refreshed himself at a cool spring after a hard day’s summer walking.”

That’s the feeling most of us miss. Even if we don’t see it, it’s there. The whispers and the smoke and remnants never disappear. Goethe was born in 1749, wrote his first bestseller which contained those words in 1774 before America was a country, and would live well into the 19th century (overlapping briefly with Jonathan the Tortoise). A hundred years after that, another famous German writer, Stefan Zweig, would be stunned to find that his elderly upstairs neighbor was the daughter of Goethe’s doctor, who had vivid memories of meeting Goethe as a young girl. In fact, Goethe had attended her christening.

Sorry, I’m getting distracted. I have too many of these wormholes and I don’t know where to put them all.

Back to the point, Ernest Hemingway opens The Sun Also Rises with a bible verse: “One generation passeth, and another generation cometh; but the earth abideth forever. The sun also riseth, and the sun goeth down, and resteth to the place where he arose.” It was this passage, his editor would say that “contained all the wisdom of the ancient world.”

And what wisdom is that? That we all flow into each other as part of an endless stream (slavery, Louis C.K. observed is just two old ladies back to back). It seems slow and long to us because we’re in it. It seems distant to us because it wasn’t our problem, it wasn’t us that did that terrible deed we’d like to forget. In fact, time whips by in a blur. Wounds barely have time to heal. They don’t recognize the passing of generations. Because generations don’t really exist. It is instead an endless parade.

When I lived in New Orleans, my apartment was partitioned out of 19th century convent. When I would head uptown to write what became my first book, I’d hop on the longest continually running streetcar in the world — some 181 years it had been traveling the same tracks. How many millions of people had ridden those same rails? Sat, even, in the same seat. Tennessee Williams, Walker Percy, Shelby Foote, George Washington Cable, Edgar Degas — could have looked out these very windows. They, along with so many others not as easily remembered — but who lived and hustled and struggled just as I was trying to.

In moments like that, one cannot help but know what Pierre Hadot has referred to as the “oceanic feeling.” A sense of belonging to something larger, realizing that “human things are an infinitesimal point in the immensity.” And when one gets this feeling, we ask ourselves important questions about who we are and what we are doing.

On the other hand, nothing draws us away from those questions like material success — when we are always busy, stressed, put upon, distracted, reported to, relied on, apart from; when we’re wealthy or told that we’re important or powerful. Ego tells us that meaning comes from activity, that being the center of attention is the only way to matter. When we lack a connection to anything larger or bigger than us, it’s like a piece of our soul is gone. Like we’ve detached ourselves from the tradition we hail from — forgetting that we’re just like the people who came before us, and we’re but a brief stopover until the people just like you who will come after. The earth abideth forever, but we will come and go.

History on the other hand, gives us perspective. As I said, it has the power to humble us. Specifically, these wormholes — illustrating the “great span” as they do — are instant humility in bite-sized pieces. It’s proof that others have been here before you, generations of them, and that they can almost reach out and touch you. In those moments, we have a sense of the immensity of the world and also its smallness. Ego is impossible, because we realize, if only fleetingly, what Emerson meant when he said that “every man is a quotation from all his ancestors” or what John Muir tried to convey to us about his epic experiences in nature. Yes, we are small. We are also a piece of this great universe and a process.

Baldwin wrote that “if you can examine and face your life, you can discover the terms with which you are connected to other lives, and they can discover them, too.” I actually think it’s the reverse. If you can examine and face the connection between other lives, and other eras, only then can you begin to understand and appreciate your own.

This post appeared originally on Boing Boing



ryan-student

Every man I meet is my master in some point, and in that I learn of him. — Ralph Waldo Emerson

The legend of Genghis Khan has echoed throughout history: A barbarian conqueror, fueled by bloodlust, terrorizing the civilized world. We have him and his Mongol horde traveling across Asia and Europe, insatiable, stopping at nothing to plunder, rape, and kill not just the people who stood in their way, but the cultures they had built. Then, not unlike his nomadic band of warriors, this terrible cloud simply disappeared from history, because the Mongols built nothing that could last.

Like all reactionary, emotional assessments, this could not be more wrong. For not only was Genghis Khan one of the greatest military minds who ever lived, he was a perpetual student, whose stunning victories were often the result of his ability to absorb the best technologies, practices, and innovations of each new culture his empire touched.

In fact, if there is one theme in his reign and in the several centuries of dynastic rule that followed, it’s this: appropriation.

Under Genghis Khan’s direction, the Mongols were as ruthless about stealing and absorbing the best of each culture they encountered as they were about conquest itself. Though there were essentially no technological inventions, no beautiful buildings or even great Mongol art, with each battle and enemy, their culture learned and absorbed something new.

Genghis Khan was not born a genius. Instead, as one biogra­pher put it, his was “a persistent cycle of pragmatic learning, experimental adaptation, and constant revision driven by his uniquely disciplined and focused will.” He was the greatest conqueror the world ever knew because he was more open to learning than any other conqueror has ever been.

Khan’s first powerful victories came from the reorganization of his military units, splitting his soldiers into groups of ten. This he stole from neighboring Turkic tribes, and unknowingly converted the Mongols to the decimal system.

Soon enough, their expanding empire brought them into contact with another “technology” they’d never experienced before: walled cities. In the Tangut raids, Khan first learned the ins and outs of war against fortified cities and the strategies critical to laying siege, and quickly became an expert. Later, with help from Chinese engineers, he taught his soldiers how to build siege machines that could knock down city walls. In his campaigns against the Jurched, Khan learned the importance of winning hearts and minds. By working with the scholars and royal family of the lands he conquered, Khan was able to hold on to and man­age these territories in ways that most empires could not.

Afterward, in every country or city he held, Khan would call for the smartest astrologers, scribes, doctors, thinkers, and advisers — anyone who could aid his troops and their efforts. His troops traveled with interrogators and translators for precisely this purpose.

It was a habit that would survive his death. While the Mongols themselves seemed dedicated almost solely to the art of war, they put to good use every craftsman, merchant, scholar, entertainer, cook, and skilled worker they came in contact with. The Mongol Empire was remarkable for its reli­gious freedoms, and most of all, for its love of ideas and con­vergence of cultures. It brought lemons to China for the first time, and Chinese noodles to the West. It spread Persian carpets, German mining technology, French metalworking, and Islam. The cannon, which revolutionized warfare, was said to be the resulting fusion of Chinese gunpowder, Mus­lim flamethrowers, and European metalwork. It was Mongol openness to learning and new ideas that brought them together.

As we first succeed, we will find ourselves in new situations, facing new problems. The freshly promoted soldier must learn the art of politics. The salesman, how to manage. The founder, how to delegate. The writer, how to edit others. The comedian, how to act. The chef turned restaurateur, how to run the other side of the house.

This is not a harmless conceit. The physicist John Wheeler, the physicist who helped develop the hydrogen bomb, once observed that “As our island of knowledge grows, so does the shore of our ignorance.” In other words, each victory and advancement that made Khan smarter also bumped him against new situations he’d never encountered before. It takes a special kind of humility to grasp that you know less, even as you know and grasp more and more. It’s remembering Socrates’ wisdom lay in the fact that he knew that he knew next to nothing.

With accomplishment comes a growing pressure to pre­tend that we know more than we do. To pretend we already know everything. Scientia infla (knowledge puffs up). That’s the worry and the risk — thinking that we’re set and secure, when in reality understanding and mastery is a fluid, con­tinual process.

The nine­-time Grammy– and Pulitzer Prize–winning jazz musician Wynton Marsalis once advised a promising young musician on the mind­set required in the lifelong study of music: “Humility engenders learning because it beats back the arrogance that puts blinders on. It leaves you open for truths to reveal themselves. You don’t stand in your own way. . . . Do you know how you can tell when someone is truly humble? I believe there’s one simple test: because they consistently observe and listen, the humble improve. They don’t assume, ‘I know the way.’” No matter what you’ve done up to this point, you better still be a student. If you’re not still learning, you’re already dying.

It is not enough only to be a student at the beginning. It is a position that one has to assume for life. Learn from everyone and everything. From the people you beat, and the people who beat you, from the people you dislike, even from your supposed enemies. At every step and every juncture in life, there is the opportunity to learn — and even if the lesson is purely remedial, we must not let ego block us from hearing it again.

It’s something I’ve had to learn as an author, personally. Just because one book does well, doesn’t mean that the next one will. It certainly doesn’t mean that everything that I’ll write is good or that I know everything there is to know about this profession either. Thinking that way is a recipe for falling off and disappointing both publishers and audiences. A better attitude is to start from scratch with each project — to focus on all there is left to learn and all the room we have left improve. That’s what I’ve tried to do with each subsequent project, including this most recent one (appropriately about ego).

Too often, convinced of our own intelligence or success, we stay in a comfort zone that ensures that we never feel stupid (and are never challenged to learn or reconsider what we know). It obscures from view various weaknesses in our under­ standing, until eventually it’s too late to change course. This is where the silent toll is taken.

Each of us faces a threat as we pursue our craft. Like sirens on the rocks, ego sings a soothing, validating song — which can lead to a wreck. The second we let the ego tell us we have graduated, learning grinds to a halt. That’s why UFC champion and MMA pioneer Frank Shamrock said, “Always stay a student.” As in, it never ends.

The solution is as straightforward as it is initially uncom­fortable: Pick up a book on a topic you know next to noth­ing about. Put yourself in rooms where you’re the least knowledgeable person. That uncomfortable feeling, that defensiveness that you feel when your most deeply held assumptions are challenged — what about subjecting your­self to it deliberately? Change your mind. Change your sur­roundings.

An amateur is defensive. The professional finds learning (and even, occasionally, being shown up) to be enjoyable; they like being challenged and humbled, and engage in education as an ongoing and endless process.

Most military cultures — and people in general — seek to impose values and control over what they encounter. What made the Mongols different was their ability to weigh each situation objectively, and if need be, swap out previous prac­tices for new ones. All great businesses start this way, but then something happens. Take the theory of disruption, which posits that at some point in time, every industry will be dis­rupted by some trend or innovation that, despite all the resources in the world, the incumbent interests will be incapable of responding to. Why is this? Why can’t businesses change and adapt? A large part of it is because they lost the ability to learn. They stopped being students. The second this happens to you, your knowledge becomes fragile.

The great manager and business thinker Peter Drucker says that it’s not enough simply to want to learn. As people progress, they must also understand how they learn and then set up processes to facilitate this continual education.

Oth­erwise, we are selling ourselves — and our careers — dreadfully short.

This piece is adapted from Ryan Holiday’s book Ego is the Enemy, published by Penguin Portfolio



“Among men who rise to fame and leadership two types are recognizable—those who are born with a belief in themselves and those in whom it is a slow growth dependent on actual achievement. To the men of the last type their own success is a constant surprise, and its fruits the more delicious, yet to be tested cautiously with a haunting sense of doubt whether it is not all a dream. In that doubt lies true modesty, not the sham of insincere self depreciation but the modesty of “moderation,” in the Greek sense. It is poise, not pose.” – B.H. Liddell Hart

When we’re young and just setting out in our careers we tend to assume that the greatest impediments to our progress and success are external to us. We blame our bosses and “the system” but we rarely think that we might be our own worst enemies, sabotaging ourselves right when we are beginning on our path.

Too often the obstacle that impedes our progress the most is internal—our own ego.

Yes, all of us, with all our talent and promise and potential, if we don’t control our ego, risk blowing up before we start. Talent, as Irving Berlin put it, is only the starting point. What we also need is self-management, self-control and humility.

Here are three ways that ego is the enemy of those important traits.

1. Talk, talk, talk.

At the beginning of any path, we’re excited and nervous. So we seek to comfort ourselves externally instead of inwardly. There’s a weak side to each of us, that—like a trade union—isn’t exactly malicious but at the end of the day still wants to get as much public credit and attention as it can for doing the least. That side we call ego.

The writer and former Gawker blogger Emily Gould—essentially a real-­life Hannah Horvath—realized this during her two-­year struggle to get a novel published. Though she had a six-­figure book deal, she was stuck. Why? She was too busy “spending a lot of time on the Internet,” that’s why.

“In fact, I can’t really remember anything else I did in 2010. I tumbld, I tweeted and I scrolled. This didn’t earn me any money but it felt like work… It was also the only creative thing I was doing.”

She did what a lot of us do when we’re scared or overwhelmed by a project—she did everything but focus on it. In fact, many valuable endeavors we undertake are painfully difficult, whether it’s coding a new startup or mastering a craft. But talking, talking is always easy. So we do that instead.

It’s a temptation that exists for everyone—for talk and hype to replace action.

Doing great work is a struggle. It’s draining, it’s demoralizing, it’s frightening—not always, but it can feel that way when we’re deep in the middle of it. We talk to fill the void and the uncertainty.

The question is, when faced with your particular challenge—­whether it is researching in a new field, starting a business, producing a film, securing a mentor, advancing an important cause—do you seek the respite of talk or do you face the struggle head­-on?

2. Early pride.

At 18, a rather triumphant Benjamin Franklin returned to visit Boston, the city he’d run away from. Full of pride, he had a new suit, a watch and a pocketful of coins that he showed to everyone he ran into. All posturing by a boy who was not much more than an employee in a print shop in Philadelphia.

In a meeting with Cotton Mather, one of the town’s most respected figures, Franklin quickly illustrated just how ridiculously inflated his young ego had become. As they walked down a hallway, Mather suddenly admonished him, “Stoop! Stoop!” Too caught up in his performance, Franklin walked right into a low ceiling beam.

Mather’s response was perfect: “Let this be a caution to you not always to hold your head so high,” he said wryly. “Stoop, young man, stoop—as you go through this world—and you’ll miss many hard thumps.”

The problem with pride is that it blunts the instrument we need to succeed—our mind. Our ability to learn, to adapt, to be flexible, to build relationships, all of this is dulled by pride. Most dangerously, this tends to happen either early in life or in the process—­when we’re flushed with beginner’s conceit. Only later do you realize that that bump on the head was the least of what was risked.

The question to ask, when you feel pride, then, is this: What am I missing right now that a more humble person might see? What am I avoiding, or running from, with my bluster, franticness, and embellishments?

It is far better to ask and answer these questions now, with the stakes still low, than it will be later.

3. Don’t be passionate.

Early on in her ascendant political career, a visitor once spoke of Eleanor Roosevelt’s “passionate interest” in a piece of social legislation. The person had meant it as a compliment. But Eleanor’s response is illustrative. “Yes,” she did support the cause, she said. “But I hardly think the word ‘passionate’ applies to me.” As a genteel, accomplished, and patient woman born while the embers of the quiet Victorian virtues were still warm, Roosevelt was above passion. She had purpose and direction.

Today it’s all about passion. Find your passion. Live passionately. Inspire the world with your passion.

People go to Burning Man to find passion, to be around passion, to rekindle their passion. Same goes for TED and the now enormous SXSW and a thousand other events, retreats and summits, all fueled by what they claim to be life’s most important force.

Here’s what those same people haven’t told you: your passion may be the very thing holding you back from power or influence or accomplishment. Because just as often, we fail with—no, because of—passion. To be clear, this is not about caring. This is passion of a different sort—unbridled enthusiasm, our willingness to pounce on what’s in front of us with the full measure of our zeal, the “bundle of energy” that our teachers and gurus have assured us is our most important asset.

Instead, what we require in our ascent is purpose. Purpose, you could say, is like passion with boundar­ies. Passion is form over function. Purpose is function, function, function. The critical work that you want to do will require your deliberation and consideration. Not passion.

Passion is about. (I am so passionate about ______.) Purpose is to and for. (I must do ______. I was put here to accomplish ______. I am willing to endure ______ for the sake of this.) Actually, purpose deemphasizes the I.

Purpose is about pursuing something outside yourself as opposed to pleasuring yourself. “Great passions are maladies without hope,” as Goethe said. Which is why a deliberate, purposeful person operates on a different level, beyond the sway or the sickness.

It’d be far better if you were intimidated by what lies ahead—humbled by its magnitude and determined to see it through regardless. Leave passion for the amateurs. Make it about your purpose: what you feel you must do and say, not what you care about and wish to be. Then you will do great things. Then you will stop being your old, good-­intentioned, but ineffective self.

Early on in our careers we are setting out to do something. We have a goal, a calling, a new beginning. Every great journey begins here—yet far too many of us never reach our intended destination. Ego more often than not is the culprit.

We build ourselves up with fantastical stories and talk, we pretend we have it all figured out, we let our star burn bright and hot only to fizzle out, and we have no idea why. These are symptoms of ego, for which humility and reality are the cure.

Do not let ego derail your career—before it even begins.

This piece is adapted from Ryan Holiday’s book Ego is the Enemy, published by Penguin Portfolio.



Sometimes there is nothing like a 900-page biography. Most of the time though, nobody has time for such a thing. Especially with many modern biographers who refuse to take a stand that resembles judgement towards their subjects.

After all, we read biographies to learn and improve ourselves, not to simply accumulate facts about someone we’ll never meet.

This leads to one of my favorite categories of books I like to recommend: moral biographies. That is, short biographical sketches about great men and women in history, written with an eye towards practical application and advice. As in, have a moral rather than about morality. They are often more anecdotal than historical, apocryphal than accurate but they get the job done. (Incidentally, this was the model I tried to base my book The Obstacle Is The Way on, though I hardly consider myself in the same league.)

Below are some of my favorites. I hope you enjoy them.

How They Succeeded: Life Stories of Successful Men Told By Themselves by Orison Swett Marden 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.

Lives of Eminent Philosophers Volumes I & II by Diogenes Laertius 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 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 (on that note, you may also like the book The Book of Dead Philosophers, a book on how many of the world’s most famous philosophers supposedly died.)

Lives of the Later Caesars by Anonymous 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.

Plutarch’s Lives 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.

The Works of Robert Greene You can argue that the master heir to this tradition is Robert Greene. What is the 48 Laws of Power but a series of biographies—moral lessons—from interesting figures in history? Naturally when I say moral I don’t mean morality, I mean the stories have a moral. From Robert Greene you can learn about Napoleon, Machiavelli, Cortez, Julius Caesar, Alexander the Great, FDR, Temple Grandin, PT Barnum, and 50 Cent in an accessible way that is really quite difficult to replicate anywhere else.

Profiles in Courage by John F. Kennedy 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.

The Lives of the Most Excellent Painters, Sculptors, and Architects by Giorgio Vasari A friend and peer of Michelangelo, Da Vinci, Raphael Titian and all the other great minds of the Renaissance sat down in 1550 and wrote biographical sketches of the people he knew or had influenced him. What I like about this book is that the profiles are not about statesmen or generals but artists. There are so many great lessons about craft and psychology within this book. The best part? It was written by someone who actually knew what he was talking about, not some art snob or critic, but an actual artist and architect of equal stature to the people he was documenting.

Founders At Work: Stories of Startups’ Early Days by Jessica Livingston 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 managed 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.

If you never took a history course, hell if your parents never taught you anything, these little books could help. They show us how to live and how not to live. And best of all, you can read about a bunch of different people in one book.

What we choose to do with that information is up to us, of course. I hope you all use it wisely and get as much out of it as I did.

And if you have room for another book of such stories, try my book The Obstacle Is The Way for stories about Amelia Earhart, Arthur Ashe, Thomas Edison, John D. Rockefeller, Dwight D. Eisenhower, and Abraham Lincoln.

This post was published originally on Thought Catalog



I originally submitted this piece to the New York Observer where I am an editor-at-large and a columnist on media and culture. Editorial decided it would no longer accept columns of this nature on this topic. I have the utmost respect for the leadership at the Observer, but I respectfully disagree with that decision.

Dad, let me start this letter by saying that it isn’t my intention to embarrass you. I find that I can express myself in writing better than I can when we talk on the phone (in fact, if anyone likes this piece, that will be, in its own way, a compliment to you — I developed as a writer sitting alone in my room as a kid, trying to find ways to respond to your overwhelming parental logic) and so when I heard that you were leaning towards voting for Donald Trump, I felt inclined to put my thoughts down so they would be clear.

It’s fitting that I would write to you here anyway, because the Observer has its own father issues when it comes to Donald Trump (Mr. Trump is the publisher’s father-in-law.) This is a newspaper that, despite its sincere and passionate reporting on anti-Semitism and its frontline investigations on the rise of Russia as a national security threat, has found itself endorsing and defending Trump…even as he veers dangerously towards courting anti-Semitism and justifying Russia’s authoritarian methods (when he isn’t complimenting the tactics of Saddam Hussein.) Having been associated with my own fair share of controversial people, I empathize with the position, Jared Kushner, the paper’s owner, must be in.

I get that elections are complicated. Yet I cannot help but feel that the right choice has become increasingly simple. Not easy, but simple.

The choice is simple because it’s hard for me to think of a single person who violates more of what you taught me as a child. The case against Donald Trump as a candidate — even as a person worthy of two seconds of anyone’s serious attention in our busy lives — is clear to me precisely because of what I learned from you, Dad.

I remember the trips we took to Angel Island in the San Francisco Bay. This is where people like Grandma and Grandpa first arrived in America, you told us. It was here that they stopped on their way to the American Dream, fleeing the terror of their homeland and hoping for a better life. You taught us that it was honorable and brave to be an immigrant and that what made America special was that we opened our arms to these people. Do you remember taking us to the Civil War battlefields and explaining how many of the men who fought and died in that war were fresh off the boat, paying for their citizenship to this country in blood — dying to eradicate the scourge of slavery, a plague they had nothing to do with creating in the first place? That was what made America great, you said.

But you didn’t just teach us to admire white European immigrants either. It was from you that I learned to respect just how hard Latino, Asian, and Middle Eastern immigrants worked to make a life for themselves here. You told me what it was like picking fruit in the California heat, and explained how they took jobs that other people weren’t willing to do — because they wanted to support their families just like everyone else. You also took the time to explain how many immigrants were entrepreneurs — starting restaurants and small businesses from donut shops to car dealerships (we’ve invested together in a few of those small businesses) and how their efforts made the world better for everyone.

When I was in Austria a few years ago, I called Mom and had her do some research to find the location of the refugee camp that Grandpa was sent to when he was just a little younger than I am now. It’s an apartment complex now, which I guess goes to show how quickly we can forget the kind of thinking that creates such horrors. Experiences like these — they color the way I see the world, which is why, I imagine, you encouraged us to travel and study history. Those trips are why I find it so repulsive to hear Donald Trump talk about how Mexicans are “rapists” and how his solution is building a literal wall — “We’re going to have a big, beautiful wall that nobody’s crossing” — to keep these kinds of people out. I find it disgusting to hear him talk about banning Muslims from America. That’s not what you taught me. That’s not how this country is supposed to work. Mom and half our relatives wouldn’t be here if it was.

I told you that a few weeks ago we had someone out at the house to repair some damage from the floods. As I was walking the property with the guy, he asked me if I owned a gun. I said that I did — this is Texas after all. “Good,” he said, “you’ll need to have something when them sand niggers come and try to take this country from us.” Then he told me about how he was glad Donald Trump was speaking the truth and taking things in the right direction.

I know you don’t agree with this man. And I don’t think it’s fair to hold a candidate accountable for every fringe group that attaches themselves to their platform. But doesn’t it alarm you to see a candidate who seems to stoke these kinds of fires — directly or indirectly? Surely you must be shaking your head at Trump’s repeated refusal to distance himself from these people.

As a police officer, you worked for a time in the hate crimes division. You’ve seen the horrible things that prejudice and ignorance can do. I remember you once told me that the way the Ku Klux Klan recruited people in our hometown was by convincing white people that they were being attacked and that their way of life was under siege. C’mon Dad, is that not eerily similar to some of Trump’s campaign tactics? Why else would he have refused to immediately disavow the support of David Duke and other white supremacists? What possible purpose did he have to insinuate that President Obama was a Muslim, that he was not born in America? Or question a Mexican-American judge’s loyalty to the law and to the Constitution?

A few years ago, Donald Trump went on live television and talked about how nice his daughter Ivanka’s body was, saying how if he wasn’t her father, he’d probably be dating her. It was disturbing then, but we all say things that come off utterly differently than intended. Except last year, speaking to a Rolling Stone reporter, Trump said the exact same thing again. “Yeah, she’s really something, and what a beauty, that one,” he told the journalist. “If I weren’t happily married and, ya know, her father…”

You have a daughter (and now a daughter-in-law). Can you imagine saying anything like that about them? What would you say to one of your friends who uttered something half that creepy? You’ve been married for thirty years. You taught me about respecting women, about the importance of marriage and fidelity. This man, he doesn’t stand for any of that. On the contrary, he refers to women he doesn’t like as “fat pigs” and “dogs.” He attacks them and when they press him on the issues, says it’s because they’re probably menstruating.

You’ve protected presidents and other heads of state as part of your job. Can you imagine any of them behaving that way? I remember our family trip to the White House in middle school — even though you disagreed with the man who was President, you spoke of the office with such reverence and dignity that we felt honored just to visit. I left that day with exactly the sense of admiration and respect for the office that I think you hoped we’d feel. I remember another trip to New York where we walked by the Trump Tower. What’s that, I asked? You just shook your head and said, “Tacky.”

Before he died, Grandad gave me his copy of John McCain’s memoir Faith of My Fathers and said that I might like to read it. It wasn’t until years later that I got around to it. Did you know that when John McCain was trapped in that horrible North Vietnamese prison, his captors offered to let him go several times? McCain’s father was the commander of all US forces in the Vietnam theater and the Vietcong thought by giving his son an easy way out, they could show that Americans were cowards. Despite the repeated torture that he’d already undergone, despite the fact that McCain ached to go home, he refused. He stayed because he refused to embarrass his country or abandon his comrades — death was better than dishonor. I think that’s the kind of lesson that Grandad was trying to pass along to me. I know you voted for McCain in 2000 and in 2008 in part for that very reason. I don’t agree with many of McCain’s politics but I hope that when tested, I could exhibit one iota of the courage that that man has.

And yet here we are discussing a Republican candidate who insulted John McCain in front of the entire world — claiming that John McCain isn’t a hero because he was captured and spent time in a POW camp. Donald Trump, who got out of serving with a series of draft deferments, said he only likes the veterans “that weren’t captured.” That this pathetic encounter has been nearly forgotten in the campaign is not because Donald addressed it or apologized, but rather because nearly every day since he either said something worse or piled on with some other obscene gesture or gaffe.

Wouldn’t just a single one of these remarks have run a candidate out of the race in a normal election cycle? Wouldn’t have these repeated and ridiculous lapses in judgement effectively end the campaign for anyone in any election anywhere in the civilized world? I’ve tried to think about why we’ve been so forgiving of Donald Trump. Is it because his opponent is a woman? Does it say something about us? Have we all collectively lost our sense of where the line is and we’re just hoping that someone will finally draw it for us?

I realize that most of these issues I’ve brought up are personal ones, but isn’t all politics personal? That’s a lesson I learned from you, too. I remember asking whether you supported the Republican or the Democrat candidate in some local election when I was a kid, having heard some friends’ parents talking about it. You told me that people got too caught up in party affiliation and that what really mattered was character and whether you could work together with the person (and whether they could do the job). That’s how I’ve tried to think all my life. I’m thinking about it now that it really matters.

The baffling reality is that when it comes to Trump, it’s difficult to critique him on much besides his personality and (lack of) character — because that is all there is. Maybe you can make an exception for some of these comments, I’ve certainly said dumb things before. We all have. Maybe we chalk them up to media mischaracterizations as some of the Trump supporters I know have (given what I write about in this column, I’m the last one to think the media is completely fair or trustworthy). But even making allowances for that, I know for a fact, no matter what the talking heads on TV are trying to tell moderate conservatives, is that you and he stand very far apart on most of the economic principles and civil policies in which you have always believed.

I remember long trips in the car and the conversation we had about civics and governance. The basics you taught me about the free market, about capitalism, about the government staying out of people’s business. Now that I’m an adult, I’ve come to fully understand and truly appreciate why you taught me these lessons. I see how they’ve contributed to my own success. I also see how the few policies or firm beliefs Trump might actually have fly in the face of all of them.

Besides repeatedly donating money to Democratic (and Republican) candidates from whom he tried to get favors, Donald Trump has said publicly that there should be “some form of punishment” for women who get abortions (though he later backtracked under pressure). He’s advocated economic policies that the experts say will start trade wars with China and Mexico. He cheered Brexit because it might drive traffic to his Scottish golf courses (the definition of a conflict of interest), has hinted at using federal resources to go after personal enemies like Jeff Bezos, admits he wouldcontinue to let his children run his numerous international businesses while in office, supports “opening up” our libel laws to reduce freedom of the press, and apparently believes that global warming is a lie created by China.

I suppose it would be one thing if these beliefs came from some unique ideological framework but we both know they don’t. He’s a man who reacts, a man who speaks before he thinks (something you always taught me to avoid). These aren’t the meticulously crafted positions of an educated leader surrounded by qualified and informed policy experts — as Trump famously said, he advises himself. There is a quote I read from Winston Churchill recently. During World War One, someone asked why he was reading the work of a certain anti-war poet. “I am not a bit afraid of Siegfried Sassoon,” Churchill said, “That man can think. I am only afraid of people who cannot think.”

I think that’s why I am so scared, Dad. That’s why I am writing you this letter. I don’t think this man has done a lick of thinking in years — except about himself and the irrational prejudices and fears which rule his increasingly erratic and bizarre life.

If my understanding of where you sit it is correct, you are inclined to agree with most of the criticisms I’ve just made and yet are swayed by very few of them. As is true for a lot of Americans, I know you’ve been disturbed with a lot what Trump has said and wish sincerely that someone else was running in his place. The problem is — the reason you can’t help but feel pressure to give him the benefit of the doubt or vote for him reluctantly — is that you feel a profound and real distrust towards Hillary Clinton.

I wasn’t old enough to experience the anger and disillusionment that the Clintons brought to the White House. I get the sense that you see them as thoughtless, careless self-aggrandizers who believe themselves to be above the law. Given the evidence, this is a more than fair assessment. You have real, negative experiences with the last administration and the vague memories of the scandals and noise of that era probably makes another four years seem unappealing. I get it.

It was J.K. Galbraith who said that politics was a matter of choosing between the disastrous and the unpalatable. I don’t disagree with you we are dealing with less than ideal options. But surely, unpalatable is better than disastrous.

Then again, no one is saying you have to vote for Hillary. I’m just asking if you could not vote for Donald Trump. Vote for a third party candidate. For a write-in, you could take a page from Trump’s people, who when they initially had trouble finding people to speak on his behalf at the convention, apparently just put “George Washington” in as a placeholder. Or, what about just not voting in this election? Is that not a powerful statement in its own right? One does not need to endorse disaster just because they resent unpalatable.

Mitt Romney has said that he was finally motivated to get involved in this election when his son asked him, “When the grandkids ask ‘What did you do to stop Donald Trump?’ what are you going to say?’”

I was so happy to be able to tell you a few weeks ago that you have your first grandchild on the way and that he’s expected to arrive just three days before the election. I think that’s why I am writing this letter too, as my way of asking myself what am I going to do to make sure the world he enters is just a little bit better than the one I came into thirty years ago. I guess I am writing this letter to ask that you, as his grandfather, do what you can to ensure the same.

So that when he does ask, not that many years in the future, looking back at what was hopefully just a painful aberration in this nation’s history, we both have a good answer to how we faced this challenge in front of us. And that we acted — despite any personal feelings, or complications or doubts — with principle and courage.

Dad, please don’t vote for Donald Trump. Everything you’ve taught me about what is wrong in the world is everything that man represents. And if you won’t do it for me, do it for your grandchild. Give him something to be proud of — and thankful for.

Your Loving Son,

Ryan