Chapter 10 


ENEMY . . .

’Tis a common proof,

That lowliness is young ambition’s ladder.


We know where we want to end up: success. We want to matter. Wealth and recognition and reputation are nice too. We want it all. The problem is that we’re not sure that humility can get us there. We are petrified, as the Reverend Dr. Sam Wells put it, that if we are humble, we will end up “subjugated, trodden on, embarrassed and irrelevant.”

   Midway through his career, if you’d asked our model Sherman how he felt, he probably would have described himself in almost exactly those terms. He had not made much money. He had won no great battles. He had not seen his name in lights or headlines. He might have, at that moment, before the Civil War, begun to question the path he’d chosen, and whether those who follow it finished last.

   This is the thinking that creates the Faustian bargain that turns most clean ambition into shameless addiction. In the early stages, ego can be temporarily adaptive. Craziness can pass for audaciousness. Delusions can pass for confidence, ignorance for courage. But it’s just kicking the costs down the road.

   Because no one ever said, reflecting on the whole of someone’s life, “Man, that monstrous ego sure was worth it.”

   The internal debate about confidence calls to mind a well-known concept from the radio pioneer Ira Glass, which could be called the Taste/Talent Gap.

   All of us who do creative work . . . we get into it because we have good taste. But it’s like there’s a gap, that for the first couple years that you’re making stuff, what you’re making isn’t so good . . . It’s really not that great. It’s trying to be good, it has ambition to be good, but it’s not quite that good. But your taste—the thing that got you into the game—your taste is still killer, and your taste is good enough that you can tell that what you’re making is kind of a disappointment to you.

   It is in precisely this gap that ego can seem comforting. Who wants to look at themselves and their work and find that it does not measure up? And so here we might bluster our way through. Cover up hard truths with sheer force of personality and drive and passion. Or, we can face our shortcomings honestly and put the time in. We can let this humble us, see clearly where we are talented and where we need to improve, and then put in the work to bridge that gap. And we can set upon positive habits that will last a lifetime.

   If ego was tempting in Sherman’s time, in this era, we are like Lance Armstrong training for the 1999 Tour de France. We are Barry Bonds debating whether to walk into the BALCO clinic. We flirt with arrogance and deceit, and in the process grossly overstate the importance of winning at all costs. Everyone is juicing, the ego says to us, you should too. There’s no way to beat them without it, we think.

   Of course, what is truly ambitious is to face life and proceed with quiet confidence in spite of the distractions. Let others grasp at crutches. It will be a lonely fight to be real, to say “I’m not going to take the edge off.” To say, “I am going to be myself, the best version of that self. I am in this for the long game, no matter how brutal it might be.” To do, not be.

   For Sherman, it was precisely his choice that prepared him for the time his country and history most needed him—and allowed him to navigate the massive responsibilities that shortly came his way. In this quiet crucible, he’d forged a personality that was ambitious but patient, innovative without being brash, brave without being dangerous. He was a real leader.

   You have a chance to do this yourself. To play a different game, to be utterly audacious in your aims. Because what comes next is going to test you in ways that you cannot begin to understand. For ego is a wicked sister of success.

   And you’re about to experience what that means.





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