Part 3


Here we are experiencing the trials endemic to any journey. Perhaps we’ve failed, perhaps our goal turned out to be harder to achieve than anticipated. No one is permanently successful, and not everyone finds success on the first attempt. We all deal with setbacks along the way. Ego not only leaves us unprepared for these circumstances, it often contributed to their occurrence in the first place. The way through, the way to rise again, requires a reorientation and increased self-awareness. We don’t need pity—our own or anyone else’s—we need purpose, poise, and patience.

It is because mankind are disposed to sympathize more entirely with our joy than with our sorrow, that we make parade of our riches, and conceal our poverty. Nothing is so mortifying as to be obliged to expose our distress to the view of the public, and to feel, that though our situation is open to the eyes of all mankind, no mortal conceives for us the half of what we suffer.


For the first half of her life, Katharine Graham saw pretty much everything go right.

   Her father, Eugene Meyer, was a financial genius who made a fortune in the stock market. Her mother was a beautiful as well as brilliant socialite. As a child, Katharine had the best of everything: the best schools, the best teachers, big houses, and servants to wait on her.

   In 1933, her father bought the Washington Post, then a struggling but important newspaper, which he began to turn around. The only child to express any serious interest in it, Katharine inherited the paper when she was older and handed over the management to her equally impressive husband, Philip Graham.

   She was not another Howard Hughes, who squandered her family’s fortune. She was not another rich kid who took the easy road in life because she could. But it was a cushy life, no question about it. She had been, in her words, content to be the tail to her husband’s (and parent’s) kite.

   Then life took a turn. Phil Graham’s behavior became increasingly erratic. He drank heavily. He made reckless business decisions and bought things they couldn’t afford. He began having affairs. He publicly humiliated his wife in front of nearly everyone they knew. Rich people problems, right? It turns out that he had suffered a severe mental breakdown, and as Katharine attempted to nurse him back to health, he killed himself with a hunting rifle while she napped in the next room.

   In 1963, at forty-six years old, Katharine Graham, a mother of three with no work experience, found herself in charge of the Washington Post Company, a vast corporation with thousands of employees. She was unprepared, timid, and naive.

   Though tragic, these events were not exactly a cataclysmic failure. Graham was still rich, still white, still privileged. Still, it was not what she thought life had planned for her. That’s the point. Failure and adversity are relative and unique to each of us. Almost without exception, this is what life does: it takes our plans and dashes them to pieces. Sometimes once, sometimes lots of times.

   As the financial philosopher and economist George Goodman once observed, it is as if “we are at a wonderful ball where the champagne sparkles in every glass and soft laughter falls upon the summer air. We know at some moment the black horsemen will come shattering through the terrace doors wreaking vengeance and scattering the survivors. Those who leave early are saved, but the ball is so splendid no one wants to leave while there is still time. So everybody keeps asking—what time is it? But none of the clocks have hands.”

   He was speaking of economic crises, although he may as well have been talking about where all of us find ourselves, not just once in our lifetimes, but often. Things are going well. Perhaps we’re aspiring to some big goal. Perhaps we’re finally enjoying the fruits of our labors. At any point, fate can intervene.

   If success is ego intoxication, then failure can be a devastating ego blow—turning slips into falls and little troubles into great unravelings. If ego is often just a nasty side effect of great success, it can be fatal during failure.

   We have many names for these problems: Sabotage. Unfairness. Adversity. Trials. Tragedy. No matter the label, it’s a trial. We don’t like it, and some of us are sunk by it. Others seem to be built to make it through. In either case, it’s a trial each person must endure.

   This fate is as much written for us as it was written five thousand years ago for the young king in Gilgamesh:

He will face a battle he knows not,

he will ride a road he knows not.

   That’s what came to Katharine Graham. It turned out that taking over the paper was the first in a series of trying and wrenching events that lasted for nearly two decades.

   Thomas Paine, remarking about George Washington, once wrote that there is a “natural firmness in some minds which cannot be unlocked by trifles, but which, when unlocked, discovers a cabinet of fortitude.” Graham seems to have possessed a similar cabinet.

   As she settled into her leadership position, Graham found that the paper’s conservative board was a constant obstacle. They were patronizing and risk averse and had held the company back. To succeed, she would have to develop her own compass and not defer to others the way she always had. It eventually became clear that she needed a new executive editor. Against the board’s advice, she replaced the well-liked good old boy with an unknown young upstart. Simple enough.

   The next turn of the screw wasn’t. Just as the company was filing to go public, the Post received a collection of stolen government documents that editors asked Graham if they could run, despite a court order preventing their publication. She consulted the company’s lawyers. She consulted the board. All advised against it—fearing it could sink the IPO or tie the company up in lawsuits for years. Torn, she decided to proceed and publish them—a decision with essentially no precedent. Shortly thereafter, the paper’s investigation of a burglary at the Democratic National Committee’s headquarters—relying on an anonymous source—threatened to put the company permanently at odds with the White House and Washington’s powerful elite (as well as jeopardizing the government licenses they needed for the TV stations the Post owned). At one point, Nixon loyalist and the attorney general of the United StatesJohn Mitchell threatened that Graham had so overreached that her “tit” was going to be “caught in a big fat wringer.” Another aide bragged that the White House was now thinking about how to screw the paper over. Put yourself in her shoes: the most powerful office in the world explicitly strategizing, “How can we hurt the Post the most?”

   On top of that, the Post’s stock price was less than stellar. The market was poor. In 1974, an investor began aggressively buying up shares in the company. The board was terrified. It could mean a hostile takeover. Graham was dispatched to deal with him. The following year, the paper’s printers’ union began a vicious, protracted strike. At one point, union members wore shirts that said, “Phil Shot the Wrong Graham.” Despite—or perhaps because of—these tactics, she decided to fight the strike. They fought back. At four o’clock one morning came a a frantic call: the union had sabotaged company machinery, beaten up an innocent staffer, and then set one of the printing presses on fire. Typically, during printing strikes competitors will help fellow papers out with their printing but Graham’s competitors refused, costing the Post $300,000 a day in advertising revenue.

   Then, a suite of major investors began to sell their stock positions in the Washington Post Company, ostensibly having lost their faith in its prospects. Graham, pushed by the activist investor she’d met with earlier, decided her best option was to spend an enormous amount of the company’s money to buy back its own shares on the public markets—a dangerous move that almost no one was doing at the time.

   That’s a list of problems exhausting to read about let alone live through. Yet because of Graham’s perseverance, it shook out better than anyone could have possibly predicted.

   The leaked documents Katharine Graham published became known as the Pentagon Papers and were one of the most important stories in the history of journalism. The paper’s Watergate reporting, which so incensed the Nixon White House, changed American history and took down an entire administration. It also won the paper a Pulitzer Prize. The investor others had feared turned out to be a young Warren Buffett, who became her business mentor and an enormous advocate and steward of the company. (His small investments in her family’s company would one day be worth hundreds of millions.) She prevailed in negotiations with the union and the strike eventually ended. Her main competitor in Washington, the one that had refused to come to her aid, the Star, suddenly folded and was acquired by the Post. Her stock buybacks—made contrary not only to business wisdom, but the judgment of the market—made the company billions of dollars.

   It turns out that the long hard slog she endured, the mistakes she made, the repeated failures, crises, and attacks were all leading somewhere. If you’d invested $1 in thePost’s IPO in 1971, it would be worth $89 by the time Graham stepped down in 1993—compared to $14 for her industry and $5 for the S&P 500. It makes her not just one of the most successful female CEOs of her generation and the first to run a Fortune 500 company, but one of the best CEOs ever, period.

   For someone born with a silver spoon in her mouth, the first decade and a half was what you’d call a baptism of fire. Graham faced difficulty after difficulty, difficulties that she wasn’t really equipped to handle, or so it seemed. There were times when it probably felt like she should have just sold the damn thing and enjoyed her massive wealth.

   Graham didn’t cause her husband’s suicide, but it was left to her to carry on without him. She didn’t ask for Watergate and the Pentagon Papers, but it fell on her to navigate their incendiary nature. While others went on buying and merger sprees in the eighties, she didn’t. She doubled down on herself and her own company, despite the fact that it was treated as a weakling by Wall Street. She could have taken the easy way a hundred times, but did not.

   At any given moment, there is the chance of failure or setbacks. Bill Walsh says, “Almost always, your road to victory goes through a place called ‘failure.’” In order to taste success again, we’ve got to understand what led to this moment (or these years) of difficulty, what went wrong and why. We must deal with the situation in order to move past it. We’ll need to accept it and to push through it.

   Graham was alone in most of this. She was blindly feeling her way through the dark, trying to figure out a tough situation she never expected to be in. She’s an example of how you can do most everything right and still find yourself in deep shit.

   We think that failure only comes to egomaniacs who were begging for it. Nixon deserved to fail; did Graham? The reality is that while yes, often people set themselves up to crash, good people fail (or other people fail them) all the time too. People who have already been through a lot find themselves stuck with more. Life isn’t fair.

   Ego loves this notion, the idea that something is “fair” or not. Psychologists call it narcissistic injury when we take personally totally indifferent and objective events. We do that when our sense of self is fragile and dependent on life going our way all the time. Whether what you’re going through is your fault or your problem doesn’t matter, because it’s yours to deal with right now. Graham’s ego didn’t cause her to fail, but if she’d had one, it certainly would have prevented her from succeeding ever again. You could say that failure always arrives uninvited, but through our ego, far too many of us allow it to stick around.

   What did Graham need through all this? Not swagger. Not bluster. She needed to be strong. She needed confidence and a willingness to endure. A sense of right and wrong.Purpose. It wasn’t about her. It was about preserving her family’s legacy. Protecting the paper. Doing her job.

   What about you? Will your ego betray you when things get difficult? Or can you proceed without it?

   When we face difficulty, particularly public difficulty (doubters, scandals, losses), our friend the ego will show its true colors.

   Absorbing the negative feedback, ego says: I knew you couldn’t do it. Why did you ever try? It claims: This isn’t worth it. This isn’t fair. This is somebody else’s problem. Why don’t you come up with a good excuse and wash your hands of this? It tells us we shouldn’t have to put up with this. It tells us that we’re not the problem.

   That is, it adds self-injury to every injury you experience.

   To paraphrase Epicurus, the narcissistically inclined live in an “unwalled city.” A fragile sense of self is constantly under threat. Illusions and accomplishments are not defenses, not when you’ve got the special sensitive antennae trained to receive (and create) the signals that challenge your precarious balancing act.

   It is a miserable way to live.

   The year before Walsh took over the 49ers, they went 2 and 14. His first year as head coach and general manager, they went . . . 2 and 14. Can you imagine the disappointment? All the changes, all the work that went into that first year, and to end up in the exact same spot as the incompetent coach who preceded you? That’s how most of us would think. And then we’d probably start blaming other people.

   Walsh realized he “had to look for evidence elsewhere” that it was turning around. For him, it was in how the games were being played, the good decisions and the changes that were being made inside the organization. Two seasons later, they won the Super Bowl and then several more after that. At rock bottom those victories must have felt like a long way off, which is why you have to be able to see past and through.

   As Goethe once observed, the great failing is “to see yourself as more than you are and to value yourself at less than your true worth.” A good metaphor might be the kind of stock buybacks that Katharine Graham made in the late seventies and eighties. Stock buybacks are controversial—they usually come from a company that is stalled or whose growth is decelerating. With buybacks, a CEO is making a rather incredible statement. She’s saying: The market is wrong. It’s valuing our company so incorrectly, and clearly has so little idea where we are heading, that we’re going to spend the company’s precious cash on a bet that they’re wrong.

   Too often, dishonest or egotistical CEOs buy back company stock because they’re delusional. Or because they want to artificially inflate the stock price. Conversely, timid or weak CEOs wouldn’t even consider betting on themselves. In Graham’s case, she made a value judgment; with Buffett’s help she could see objectively that the market didn’t appreciate the true worth of the company’s assets. She knew that the reputational hits, the learning curve, had all contributed to a suppressed stock price, which aside from reducing her personal wealth, created a massive opportunity for the company. Over a short period, she would buy nearly 40 percent of the company’s shares at a fraction of what they’d later be worth. The stock that Katharine Graham bought for approximately $20 a share would less than a decade later be worth more than $300.

   What both Graham and Walsh were doing was adhering to a set of internal metrics that allowed them to evaluate and gauge their progress while everyone on the outside was too distracted by supposed signs of failure or weakness.

   This is what guides us through difficulty.

   You might not get into your first choice college. You might not get picked for the project or you might get passed over for the promotion. Someone might outbid you for the job, for your dream house, for the opportunity you feel everything depends on. This might happen tomorrow, it might happen twenty-five years from now. It could last for two minutes or ten years. We know that everyone experiences failure and adversity, that we’re all subject to the rules of gravity and averages. What does that mean? It means we’ll face them too.

   As Plutarch finely expressed, “The future bears down upon each one of us with all the hazards of the unknown.” The only way out is through.

   Humble and strong people don’t have the same trouble with these troubles that egotists do. There are fewer complaints and far less self-immolation. Instead, there’s stoic—even cheerful—resilience. Pity isn’t necessary. Their identity isn’t threatened. They can get by without constant validation.

   This is what we’re aspiring to—much more than mere success. What matters is that we can respond to what life throws at us.

   And how we make it through.

Chapter 20


Vivre sans temps mort. (Live without wasted time.)


Malcolm X was a criminal. He wasn’t Malcolm X at the time—they called him Detroit Red and he was a criminal opportunist who did a little bit of everything. He ran numbers. He sold drugs. He worked as a pimp. Then he moved up to armed robbery. He had his own burglary gang, which he ruled over with a combination of intimidation and boldness—exploiting the fact that he did not seem afraid to kill or die.

   Then, finally, he was arrested trying to fence an expensive watch he’d stolen. He was carrying a gun at the time, though to his credit he made no move to fight the officers who had trapped him. In his apartment, they found jewelry, furs, an arsenal of guns, and all his burglary tools.

   He got ten years. It was February 1946. He was barely twenty-one years old.

   Even accounting for the shameful American racism and whatever systematic legal injustices existed at the time, Malcolm X was guilty. He deserved to go to jail. Who knows who else he would have hurt or killed had he continued his escalating life of crime?

   When your actions land you a lengthy prison sentence—rightly tried and convicted—something has gone wrong. You’ve failed not only yourself, but the basic standards of society and morality. That was the case with Malcolm.

   So there he was in prison. A number. A body with roughly a decade to sit in a cage.

   He faced what Robert Greene—a man who sixty years later would find his wildly popular books banned in many federal prisons—calls an “Alive Time or Dead Time” scenario. How would the seven years ultimately play out? What would Malcolm do with this time?

   According to Greene, there are two types of time in our lives: dead time, when people are passive and waiting, and alive time, when people are learning and acting and utilizing every second. Every moment of failure, every moment or situation that we did not deliberately choose or control, presents this choice: Alive time. Dead time.

   Which will it be?

   Malcolm chose alive time. He began to learn. He explored religion. He taught himself to be a reader by checking out a pencil and the dictionary from the prison library and not only consumed it from start to finish, but copied it down longhand from cover to cover. All these words he’d never known existed before were transferred to his brain.

   As he said later, “From then until I left that prison, in every free moment I had, if I was not reading in the library, I was reading in my bunk.” He read history, he read sociology, he read about religion, he read the classics, he read philosophers like Kant and Spinoza. Later, a reporter asked Malcolm, “What’s your alma mater?” His one word answer: “Books.” Prison was his college. He transcended confinement through the pages he absorbed. He reflected that months passed without his even thinking about being detained against his will. He had “never been so truly free in his life.”

   Most people know what Malcolm X did after he got out of prison, but they don’t realize or understand how prison made that possible. How a mix of acceptance, humility, and strength powered the transformation. They also aren’t aware of how common this is in history, how many figures took seemingly terrible situations—a prison sentence, an exile, a bear market or depression, military conscription, even being sent to a concentration camp—and through their attitude and approach, turned those circumstances into fuel for their unique greatness.

   Francis Scott Key wrote the poem that became the national anthem of the United States while trapped on a ship during a prisoner exchange in the War of 1812. Viktor Frankl refined his psychologies of meaning and suffering during his ordeal in three Nazi concentration camps.

   Not that these opportunities always come in such serious situations. The author Ian Fleming was on bed rest and, per doctors’ orders, forbidden from using a typewriter. They were worried he’d exert himself by writing another Bond novel. So he created Chitty Chitty Bang Bang by hand instead. Walt Disney made his decision to become a cartoonist while laid up after stepping on a rusty nail.

   Yes, it would feel much better in the moment to be angry, to be aggrieved, to be depressed or heartbroken. When injustice or the capriciousness of fate are inflicted on someone, the normal reaction is to yell, to fight back, to resist. You know the feeling: I don’t want this. I want ______. I want it my way. This is shortsighted.

   Think of what you have been putting off. Issues you declined to deal with. Systemic problems that felt too overwhelming to address. Dead time is revived when we use it as an opportunity to do what we’ve long needed to do.

   As they say, this moment is not your life. But it is a momentin your life. How will you use it?

   Malcolm could have doubled down on the life that brought him to prison. Dead time isn’t only dead because of sloth or complacency. He could have spent those years becoming a better criminal, strengthening his contacts, or planning his next score, but it still would have been dead time. He might have felt alive doing it, even as he was slowly killing himself.

   “Many a serious thinker has been produced in prisons,” as Robert Greene put it, “where we have nothing to do but think.” Yet sadly, prisons—in their literal and figurative forms—have produced far more degenerates, losers, and ne’er-do-wells. Inmates might have had nothing to do but think; it’s just that what they chose to think about made them worse and not better.

   That’s what so many of us do when we fail or get ourselves into trouble. Lacking the ability to examine ourselves, we reinvest our energy into exactly the patterns of behavior that caused our problems to begin with.

   It comes in many forms. Idly dreaming about the future. Plotting our revenge. Finding refuge in distraction. Refusing to consider that our choices are a reflection of our character. We’d rather do basically anything else.

   But what if we said: This is an opportunity for me. I am using it for my purposes. I will not let this be dead time for me.

   The dead time was when we were controlled by ego. Now—now we can live.

   Who knows what you’re currently doing. Hopefully it’s not a prison term, even if it might feel like it. Maybe you’re sitting in a remedial high school class, maybe you’re on hold, maybe it’s a trial separation, maybe you’re making smoothies while you save up money, maybe you’re stuck waiting out a contract or a tour of duty. Maybe this situation is one totally of your own making, or perhaps it’s just bad luck.

   In life, we all get stuck with dead time. Its occurrence isn’t in our control. Its use, on the other hand, is.

   As Booker T. Washington most famously put it, “Cast down your bucket where you are.” Make use of what’s around you. Don’t let stubbornness make a bad situation worse.





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