At the time—and unfairly, I think now—I judged him for the swerve. I had no capacity to understand why someone would take an expensive Princeton education and not immediately convert it into the kind of leg up in the world that such a degree was meant to yield. Why, when you could be in medical school, would you be a dog who does handsprings?
But that was me. And as I’ve said, I was a box checker—marching to the resolute beat of effort/result, effort/result—a devoted follower of the established path, if only because nobody in my family （aside from Craig） had ever set foot on the path before. I wasn’t particularly imaginative in how I thought about the future, which is another way of saying I was already thinking about law school.
Life on Euclid Avenue had taught me—maybe forced me—to be hard-edged and practical about both time and money. The biggest swerve I’d ever made was a decision to spend the first part of the summer after sophomore year working for basically nothing as a camp counselor in New York’s Hudson Valley, looking after urban kids who were having their first experiences in the woods. I’d loved the job but came out of it more or less broke, more dependent on my parents financially than I wanted to be. Though they never once complained, I’d feel guilty about it for years to come.
This was the same summer, too, when people I loved started to die. Robbie, my great-aunt, my rigid taskmaster of a piano teacher, passed away in June, bequeathing her house on Euclid to my parents, allowing them to become home owners for the first time. Southside died a month later after having suffered with advanced lung cancer, his long-held view that doctors were untrustworthy having kept him from any sort of timely intervention. After Southside’s funeral, my mother’s enormous family piled into his snug little home, along with a smattering of friends and neighbors. I felt the warm tug of the past and the melancholy of absence—all of it a little jarring, accustomed as I was to the hermetic and youthful world of college. It was something deeper than what I normally felt at school, the slow shift of generational gears. My kid cousins were full grown; my aunts had grown old. There were new babies and new spouses. A jazz album roared from the home-built stereo shelves in the dining room, and we dined on a potluck brought by loved ones—baked ham, Jell-O molds, and casseroles. But Southside himself was gone. It was painful, but time pushed us all forward.
* * *
Each spring, corporate recruiters descended on the Princeton campus, aiming themselves at the graduating seniors. You’d see a classmate who normally dressed in ratty jeans and an untucked shirt crossing campus in a pin-striped suit and understand that he or she was destined for a Manhattan skyscraper. It happened quickly, this vocational sorting—the bankers, lawyers, doctors, and executives of tomorrow hastily migrating toward their next launchpad, whether it was graduate school or a cushy Fortune 500 training-program job. I’m certain there were others among us who followed their hearts into education, the arts, and nonprofit work or who went off on Peace Corps missions or to serve in the military, but I knew very few of them. I was busy climbing my ladder, which was sturdy and practical and aimed straight up.
If I’d stopped to think about it, I might have realized that I was burned-out by school—by the grind of lectures, papers, and exams—and probably would have benefited from doing something different. Instead I took the LSAT, wrote my senior thesis, and dutifully reached for the next rung, applying to the best law schools in the country. I saw myself as smart, analytical, and ambitious. I’d been raised on feisty dinner-table debates with my parents. I could argue a point down to its theoretical essence and prided myself on never rolling over in a conflict. Was this not the stuff lawyers were made of? I figured it was.
I can admit now that I was driven not just by logic but by some reflexive wish for other people’s approval, too. When I was a kid, I quietly basked in the warmth that floated my way anytime I announced to a teacher, a neighbor, or one of Robbie’s church-choir friends that I wanted to be a pediatrician. My, isn’t that impressive? their expressions would say, and I reveled in it. Years later, it was really no different. Professors, relatives, random people I met, asked what was next for me, and when I mentioned I was bound for law school—Harvard Law School, as it turned out—the affirmation was overwhelming. I was applauded just for getting in, even if the truth was I’d somehow squeaked in off the wait list. But I was in. People looked at me as if already I’d made my mark on the world.
This may be the fundamental problem with caring a lot about what others think: It can put you on the established path—the my-isn’t-that-impressive path—and keep you there for a long time. Maybe it stops you from swerving, from ever even considering a swerve, because what you risk losing in terms of other people’s high regard can feel too costly. Maybe you spend three years in Massachusetts, studying constitutional law and discussing the relative merits of exclusionary vertical agreements in antitrust cases. For some, this might be truly interesting, but for you it is not. Maybe during those three years you make friends you’ll love and respect forever, people who seem genuinely called to the bloodless intricacies of the law, but you yourself are not called. Your passion stays low, yet under no circumstance will you underperform. You live, as you always have, by the code of effort/result, and with it you keep achieving until you think you know the answers to all the questions—including the most important one. Am I good enough? Yes, in fact I am.
What happens next is that the rewards get real. You reach for the next rung of the ladder, and this time it’s a job with a salary in the Chicago offices of a high-end law firm called Sidley & Austin. You’re back where you started, in the city where you were born, only now you go to work on the forty-seventh floor in a downtown building with a wide plaza and a sculpture out front. You used to pass by it as a South Side kid riding the bus to high school, peering mutely out the window at the people who strode like titans to their jobs. Now you’re one of them. You’ve worked yourself out of that bus and across the plaza and onto an upward-moving elevator so silent it seems to glide. You’ve joined the tribe. At the age of twenty-five, you have an assistant. You make more money than your parents ever have. Your co-workers are polite, educated, and mostly white. You wear an Armani suit and sign up for a subscription wine service. You make monthly payments on your law school loans and go to step aerobics after work. Because you can, you buy yourself a Saab.
Is there anything to question? It doesn’t seem that way. You’re a lawyer now. You’ve taken everything ever given to you—the love of your parents, the faith of your teachers, the music from Southside and Robbie, the meals from Aunt Sis, the vocabulary words drilled into you by Dandy—and converted it to this. You’ve climbed the mountain. And part of your job, aside from parsing abstract intellectual property issues for big corporations, is to help cultivate the next set of young lawyers being courted by the firm. A senior partner asks if you’ll mentor an incoming summer associate, and the answer is easy: Of course you will. You have yet to understand the altering force of a simple yes. You don’t know that when a memo arrives to confirm the assignment, some deep and unseen fault line in your life has begun to tremble, that some hold is already starting to slip. Next to your name is another name, that of some hotshot law student who’s busy climbing his own ladder. Like you, he’s black and from Harvard. Other than that, you know nothing—just the name, and it’s an odd one.