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