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INTRODUCTION

The first principle is that you must not fool yourself—and you are the easiest person to fool.

—RICHARD FEYNMAN

Maybe you’re young and brimming with ambition. Maybe you’re young and you’re struggling. Maybe you’ve made that first couple million, signed your first deal, been selected to some elite group, or maybe you’re already accomplished enough to last a lifetime. Maybe you’re stunned to find out how empty it is at the top. Maybe you’re charged with leading others through a crisis. Maybe you just got fired. Maybe you just hit rock bottom.

Wherever you are, whatever you’re doing, your worst enemy already lives inside you: your ego.

“Not me,” you think. “No one would ever call me an egomaniac.” Perhaps you’ve always thought of yourself as a pretty balanced person. But for people with ambitions, talents, drives, and potential to fulfill, ego comes with the territory. Precisely what makes us so promising as thinkers, doers, creatives, and entrepreneurs, what drives us to the top of those fields, makes us vulnerable to this darker side of the psyche.

Now this is not a book about ego in the Freudian sense. Freud was fond of explaining the ego by way of analogy—our ego was the rider on a horse, with our unconscious drives representing the animal while the ego tried to direct them. Modern psychologists, on the other hand, use the word “egotist” to refer to someone dangerously focused on themselves and with disregard for anyone else. All these definitions are true enough but of little value outside a clinical setting.

The ego we see most commonly goes by a more casual definition: an unhealthy belief in our own importance. Arrogance. Self-centered ambition. That’s the definition this book will use. It’s that petulant child inside every person, the one that chooses getting his or her way over anything or anyone else. The need to be better than, more than, recognized for, far past any reasonable utility—that’s ego. It’s the sense of superiority and certainty that exceeds the bounds of confidence and talent.

It’s when the notion of ourselves and the world grows so inflated that it begins to distort the reality that surrounds us. When, as the football coach Bill Walsh explained, “self-confidence becomes arrogance, assertiveness becomes obstinacy, and self-assurance becomes reckless abandon.” This is the ego, as the writer Cyril Connolly warned, that “sucks us down like the law of gravity.” In this way, ego is the enemy of what you want and of what you have: Of mastering a craft. Of real creative insight. Of working well with others. Of building loyalty and support. Of longevity. Of repeating and retaining your success. It repulses advantages and opportunities. It’s a magnet for enemies and errors. It is Scylla and Charybdis.

Most of us aren’t “egomaniacs,” but ego is there at the root of almost every conceivable problem and obstacle, from why we can’t win to why we need to win all the time and at the expense of others. From why we don’t have what we want to why having what we want doesn’t seem to make us feel any better.

We don’t usually see it this way. We think something else is to blame for our problems (most often, other people). We are, as the poet Lucretius put it a few thousand years ago, the proverbial “sick man ignorant of the cause of his malady.” Especially for successful people who can’t see what ego prevents them from doing because all they can see is what they’ve already done.

With every ambition and goal we have—big or small—ego is there undermining us on the very journey we’ve put everything into pursuing.

The pioneering CEO Harold Geneen compared egoism to alcoholism: “The egotist does not stumble about, knocking things off his desk. He does not stammer or drool. No, instead, he becomes more and more arrogant, and some people, not knowing what is underneath such an attitude, mistake his arrogance for a sense of power and self-confidence.” You could say they start to mistake that about themselves too, not realizing the disease they’ve contracted or that they’re killing themselves with it.

If ego is the voice that tells us we’re better than we really are, we can say ego inhibits true success by preventing a direct and honest connection to the world around us. One of the early members of Alcoholics Anonymous defined ego as “a conscious separation from.” From what? Everything.

The ways this separation manifests itself negatively are immense: We can’t work with other people if we’ve put up walls. We can’t improve the world if we don’t understand it or ourselves. We can’t take or receive feedback if we are incapable of or uninterested in hearing from outside sources. We can’t recognize opportunities—or create them—if instead of seeing what is in front of us, we live inside our own fantasy. Without an accurate accounting of our own abilities compared to others, what we have is not confidence but delusion. How are we supposed to reach, motivate, or lead other people if we can’t relate to their needs—because we’ve lost touch with our own?

The performance artist Marina Abramović puts it directly: “If you start believing in your greatness, it is the death of your creativity.” Just one thing keeps ego around—comfort. Pursuing great work—whether it is in sports or art or business—is often terrifying. Ego soothes that fear. It’s a salve to that insecurity. Replacing the rational and aware parts of our psyche with bluster and self-absorption, ego tells us what we want to hear, when we want to hear it.

But it is a short-term fix with a long-term consequence.

EGO WAS ALWAYS THERE. NOW IT’S EMBOLDENED.

Now more than ever, our culture fans the flames of ego. It’s never been easier to talk, to puff ourselves up. We can brag about our goals to millions of our fans and followers—things only rock stars and cult leaders used to have. We can follow and interact with our idols on Twitter, we can read books and sites and watch TED Talks, drink from a fire hose of inspiration and validation like never before (there’s an app for that). We can name ourselves CEO of our exists-only-on-paper company. We can announce big news on social media and let the congratulations roll in. We can publish articles about ourselves in outlets that used to be sources of objective journalism.

Some of us do this more than others. But it’s only a matter of degree.

Besides the changes in technology, we’re told to believe in our uniqueness above all else. We’re told to think big, live big, to be memorable and “dare greatly.” We think that success requires a bold vision or some sweeping plan—after all, that’s what the founders of this company or that championship team supposedly had. (But did they? Did they really?) We see risk-taking swagger and successful people in the media, and eager for our own successes, try to reverse engineer the right attitude, the right pose.

We intuit a causal relationship that isn’t there. We assume the symptoms of success are the same as success itself—and in our naiveté, confuse the by-product with the cause.

Sure, ego has worked for some. Many of history’s most famous men and women were notoriously egotistical. But so were many of its greatest failures. Far more of them, in fact. But here we are with a culture that urges us to roll the dice. To make the gamble, ignoring the stakes.

WHEREVER YOU ARE, EGO IS TOO.

At any given time in life, people find themselves at one of three stages. We’re aspiring to something—trying to make a dent in the universe. We have achieved success—perhaps a little, perhaps a lot. Or we have failed—recently or continually. Most of us are in these stages in a fluid sense—we’re aspiring until we succeed, we succeed until we fail or until we aspire to more, and after we fail we can begin to aspire or succeed again.

Ego is the enemy every step along this way. In a sense, ego is the enemy of building, of maintaining, and of recovering. When things come fast and easy, this might be fine. But in times of change, of difficulty . . .

And therefore, the three parts that this book is organized into: Aspire. Success. Failure.

The aim of that structure is simple: to help you suppress ego early before bad habits take hold, to replace the temptations of ego with humility and discipline when we experience success, and to cultivate strength and fortitude so that when fate turns against you, you’re not wrecked by failure. In short, it will help us be: Humble in our aspirations

Gracious in our success

Resilient in our failures

This is not to say that you’re not unique and that you don’t have something amazing to contribute in your short time on this planet. This is not to say that there is not room to push past creative boundaries, to invent, to feel inspired, or to aim for truly ambitious change and innovation. On the contrary, in order to properly do these things and take these risks we need balance. As the Quaker William Penn observed, “Buildings that lie so exposed to the weather need a good foundation.” SO, WHAT NOW?

This book you hold in your hands is written around one optimistic assumption: Your ego is not some power you’re forced to satiate at every turn. It can be managed. It can be directed.

In this book, we’ll look at individuals like William Tecumseh Sherman, Katharine Graham, Jackie Robinson, Eleanor Roosevelt, Bill Walsh, Benjamin Franklin, Belisarius, Angela Merkel, and George C. Marshall. Could they have accomplished what they accomplished—saving faltering companies, advancing the art of war, integrating baseball, revolutionizing football offense, standing up to tyranny, bravely bearing misfortune—if ego had left them ungrounded and self-absorbed? It was their sense of reality and awareness—one that the author and strategist Robert Greene once said we must take to like a spider in its web—that was at the core of their great art, great writing, great design, great business, great marketing, and great leadership.

What we find when we study these individuals is that they were grounded, circumspect, and unflinchingly real. Not that any of them were wholly without ego. But they knew how to suppress it, channel it, subsume it when it counted. They were great yet humble.

Wait, but so-and-so had a huge ego and was successful. But what about Steve Jobs? What about Kanye West?

We can seek to rationalize the worst behavior by pointing to outliers. But no one is truly successful because they are delusional, self-absorbed, or disconnected. Even if these traits are correlated or associated with certain well-known individuals, so are a few others: addiction, abuse (of themselves and others), depression, mania. In fact, what we see when we study these people is that they did their best work in the moments when they fought back against these impulses, disorders, and flaws. Only when free of ego and baggage can anyone perform to their utmost.

For this reason, we’re also going to look at individuals like Howard Hughes, the Persian king Xerxes, John DeLorean, Alexander the Great, and at the many cautionary tales of others who lost their grip on reality and in the process made it clear what a gamble ego can be. We’ll look at the costly lessons they learned and the price they paid in misery and self-destruction. We’ll look at how often even the most successful people vacillate between humility and ego and the problems this causes.

When we remove ego, we’re left with what is real. What replaces ego is humility, yes—but rock-hard humility and confidence. Whereas ego is artificial, this type of confidence can hold weight. Ego is stolen. Confidence is earned. Ego is self-anointed, its swagger is artifice. One is girding yourself, the other gaslighting. It’s the difference between potent and poisonous.

As you’ll see in the pages that follow, that self-confidence took an unassuming and underestimated general and turned him into America’s foremost warrior and strategist during the Civil War. Ego took a different general from the heights of power and influence after that same war and drove him to destitution and ignominy. One took a quiet, sober German scientist and made her not just a new kind of leader but a force for peace. The other took two different but equally brilliant and bold engineering minds of the twentieth century and built them up in a whirlwind of hype and celebrity before dashing their hopes against the rocks of failure, bankruptcy, scandal, and insanity. One guided one of the worst teams in NFL history to the Super Bowl in three seasons, and then on to be one of most dominant dynasties in the game. Meanwhile, countless other coaches, politicians, entrepreneurs, and writers have overcome similar odds—only to succumb to the more inevitable probability of handing the top spot right back to someone else.

Some learn humility. Some choose ego. Some are prepared for the vicissitudes of fate, both positive and negative. Others are not. Which will you choose? Who will you be?

You’ve picked up this book because you sense that you’ll need to answer this question eventually, consciously or not.

Well, here we are. Let’s get to it.