Esquire Classics
What I’ve Learned
6 min readJun 25, 2015

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I was born into an era where opportunity was far from guaranteed for people who looked like me.

I believe deeply that whether you grew up in Ouagadougou or Paris, there is a place for you, and hope for you.

My mother’s family came from Portland, Maine. My grandparents on my mother’s side emigrated from Jamaica to Portland in 1912, which was not a traditional route. My grandfather was a janitor and a cobbler who never finished high school. My grandmother was a maid and a seamstress who didn’t get beyond the ninth grade. They had five children, and sent all five to first-rate colleges, and all five became professionals. My father’s family was from South Carolina, the descendants of slaves. But my father’s parents were highly educated. My grandfather was a minister in the AME church. My grandmother was a schoolteacher. Both of them also went to college.

I was taught to believe that I would succeed because I was good. I believe what I believe because of the example of these people.

My father was born in 1919, in segregated South Carolina. He served in the segregated armed forces at Tuskegee, an experience that affected him profoundly. This is someone who graduated from City College of New York at age twenty, received his Ph.D. in economics from Berkeley, was on the faculty at Cornell. Appointed to the Federal Reserve Board. A man of enormous talent. But he was born in an era when the doors were closed, the expectations were very low, and there were many things he was told throughout his life that he couldn’t do. Like eat at a lunch counter. Or serve on an equal level in the United States military. He came out of the segregated army very resentful at the injustice of that experience. And so his life was one of having to prove despite the barriers that he could fulfill his potential, which he did. Struggle, incredible struggle.

I was hugely privileged to never be burdened by the notion that I couldn’t do what I wanted to do. Which is a completely different mentality than that which my father was raised with. His experience taught me to feel unbound and undaunted.

When I was growing up, he never shared his frustrations with me. I didn’t fully appreciate his situation until I was grown. He shielded me and my brother. He was determined that we never feel those limits.

I went to an academically rigorous, highly competitive girls’ high school in Washington, D.C. I worked so hard in high school that frankly, nothing has seemed as hard since.

When you’re fifteen and you’re grinding it out under high pressure and stress, you could argue that that’s not healthy. I could be persuaded of that. But it’s a heck of a way to build early skills of focus and discipline and a belief that hard problems can be tackled through intellectual effort, but also through just plain rigor.

Most instructive failure? Believing too much that if you work hard and do your best, are honest and do things with the right motivation, that that will be enough. I learned two years ago in the context of Benghazi that that’s not necessarily true, that things are sometimes profoundly not fair.

So many things. One, that this is not often a rational town. And that people are willing to distort and manipulate for their own reasons, and then turn around and be friendly with you privately. I’ve had more people viciously attack me in public then tell me, You’re a good person, in private. Like it’s a game, it’s a sport. This does not go unnoticed.

I don’t know what I learned from other people’s misjudgment of me. I don’t know what’s in their heads and can’t worry about that too much. I have learned much more from my misjudgments of others. You’ve got to regard people as individuals. You shouldn’t make snap judgments. I’ve learned I can be wrong. The older I get, the slower I am to judge.

Sometimes it’s better than you think. I sleep pretty well most nights.

There are many more things that could go wrong than do go wrong.

It’s a whole lot easier being outside government second-guessing than being inside and responsible. It’s so much easier to criticize and carp.

You cannot just accept the analysis that conforms to your predispositions. You must welcome contrary information. Things aren’t always as they at first seem to be or as you wish them to be.

One of the great privileges in serving as the National Security Advisor of the United States of America, the most powerful country in the world, is that we do have a lot that we can do. We don’t have a magic wand and we can’t solve every problem with the wave of a hand. There are some intractable problems out there that aren’t amenable to imposed solutions from anybody on the outside. But it’s not a sense that we lack power. It’s the sense that the nature of those problems is such that our power isn’t the proper tool to unlock the problem.

Often, it’s not the best of good options. It’s the least bad of horrible options. That’s the reality in the business I’m in. In Libya, a bad option was having to get involved. A worse option was doing nothing.

It’s not just the wolf at the door but what might come down the road long after I’m gone.

I don’t have a great deal of capacity or bandwidth to deal with what came ten or more years ago. I’m thinking about what’s happening today, what’s coming tomorrow. I learn from Iraq and from other situations my predecessors have faced, but with the challenges of this job, I cannot be obsessing about the past. And I say that as a historian.

I don’t fully remember my conception of God when I was six. God was in the book I was reading or the tree I was climbing or the ball I was throwing.

I wish I’d joined the Peace Corps. Because so much of my subsequent life has been about people whose experiences are different from our own. It doesn’t matter where, it just matters that you leave your comfort zone. That’s an experience that stays with you. And that’s something I might yet do.

When I was younger, I knew at any given time what I wanted to do, but I didn’t know what I ultimately wanted to do. I still don’t know what I ultimately want to do.

For more wisdom and life lessons from world leaders, cultural icons, and athletes, head to Esquire.com.

Cover photo by Ben Baker/Redux

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