Two, I am getting very serious in my relationship with Barack and I feel that I need to get a better handle on myself.
This little flowered book has now survived a couple of decades and multiple moves. It sat on a shelf in my dressing room at the White House for eight years, until very recently, when I pulled it out from a box in my new home to try to reacquaint myself with who I’d been as a young lawyer. I read those lines today and see exactly what I was trying to tell myself—what a no-nonsense female mentor might have said to me directly. Really, it was simple: The first thing was that I hated being a lawyer. I wasn’t suited to the work. I felt empty doing it, even if I was plenty good at it. This was a distressing thing to admit, given how hard I’d worked and how in debt I was. In my blinding drive to excel, in my need to do things perfectly, I’d missed the signs and taken the wrong road.
The second was that I was deeply, delightfully in love with a guy whose forceful intellect and ambition could possibly end up swallowing mine. I saw it coming already, like a barreling wave with a mighty undertow. I wasn’t going to get out of its path—I was too committed to Barack by then, too in love—but I did need to quickly anchor myself on two feet.
This meant finding a new profession, and what shook me most was that I had no concrete ideas about what I wanted to do. Somehow, in all my years of schooling, I hadn’t managed to think through my own passions and how they might match up with work I found meaningful. As a young person, I’d explored exactly nothing. Barack’s maturity, I realized, came in part from the years he’d logged as a community organizer and even, prior to that, a decidedly unfulfilling year he’d spent as a researcher at a Manhattan business consulting firm immediately after college. He’d tried out some things, gotten to know all sorts of people, and learned his own priorities along the way. I, meanwhile, had been so afraid of floundering, so eager for respectability and a way to pay the bills, that I’d marched myself unthinkingly into the law.
In the span of a year, I’d gained Barack and lost Suzanne, and the power of those two things together had left me spinning. Suzanne’s sudden death had awakened me to the idea that I wanted more joy and meaning in my life. I couldn’t continue to live with my own complacency. I both credited and blamed Barack for the confusion. “If there were not a man in my life constantly questioning me about what drives me and what pains me,” I wrote in my journal, “would I be doing it on my own?”
I mused about what I might do, what skills I might possibly have. Could I be a teacher? A college administrator? Could I run some sort of after-school program, a professionalized version of what I’d done for Czerny at Princeton? I was interested in possibly working for a foundation or a nonprofit. I was interested in helping underprivileged kids. I wondered if I could find a job that engaged my mind and still left me enough time to do volunteer work, or appreciate art, or have children. I wanted a life, basically. I wanted to feel whole. I made a list of issues that interested me: education, teen pregnancy, black self-esteem. A more virtuous job, I knew, would inevitably involve a pay cut. More sobering was my next list, this one of my essential expenses—what was left after I let go of the luxuries I’d allowed myself on a Sidley salary, things like my subscription wine service and health-club membership. I had a $600 monthly payment on my student loans, a $407 car payment, money spent on food, gas, and insurance, plus the roughly $500 a month I’d need for rent if I ever moved out of my parents’ house.
Nothing was impossible, but nothing looked simple, either. I started asking around about opportunities in entertainment law, thinking perhaps that it might be interesting and would also spare me the sting of a lower salary. But in my heart, I felt a slow-growing certainty of my own: I wasn’t built to practice law. One day I made note of a New York Times article I’d read that reported widespread fatigue, stress, and unhappiness among American lawyers—most especially female ones. “How depressing,” I wrote in my journal.
* * *
I spent a good chunk of that August toiling in a rented conference room at a hotel in Washington, D.C., having been dispatched to help prepare a case. Sidley & Austin was representing the chemical conglomerate Union Carbide in an antitrust trial involving the sale of one of its business holdings. I stayed in Washington for about three weeks but managed to see very little of the city, because my life was wholly dedicated to sitting in that room with several Sidley peers, opening file boxes that had been shipped from the company headquarters, and reviewing the thousands of pages of documents inside.
You wouldn’t think I’d be the type of person to find psychic relief in the intricacies of the urethane polyether polyol trade, but I did. I was still practicing law, but the specificity of the work and the change of scenery distracted me just enough from the bigger questions beginning to bubble up in my mind.
Ultimately, the chemical case was settled out of court, which meant that much of my document reviewing had been for nothing. This was an irksome but expected trade-off in the legal field, where it was not uncommon to prepare for a trial that never came to pass. On the evening I flew home to Chicago, I felt a heavy dread settling over me, knowing that I was about to step back into my everyday routine and the fog of my confusion.
My mother was kind enough to meet my flight at O’Hare. Just seeing her gave me comfort. She was in her early fifties now, working full-time as an executive assistant at a downtown bank, which as she described it was basically a bunch of men sitting at desks, having gone into the business because their fathers had been bankers before them. My mother was a force. She had little tolerance for fools. She kept her hair short and wore practical, unfussy clothes. Everything about her radiated competence and calm. As it had been when Craig and I were kids, she didn’t get involved with our private lives. Her love came in the form of reliability. She showed up when your flight came in. She drove you home and offered food if you were hungry. Her even temper was like shelter to me, a place to seek refuge.
As we drove downtown toward the city, I heaved a big sigh.
“You okay?” my mom asked.
I looked at her in the half-light of the freeway. “I don’t know,” I began. “It’s just…”
And with that, I unloaded my feelings. I told her that I wasn’t happy with my job, or even with my chosen profession—that I was seriously unhappy, in fact. I told her about my restlessness, how I was desperate to make a major change but worried about not making enough money if I did. My emotions were raw. I let out another sigh. “I’m just not fulfilled,” I said.
I see now how this must have come across to my mother, who was then in the ninth year of a job she’d taken primarily so she could help finance my college education, after years of not having a job so that she’d be free to sew my school clothes, cook my meals, and do laundry for my dad, who for the sake of our family spent eight hours a day watching gauges on a boiler at the filtration plant. My mom, who’d just driven an hour to fetch me from the airport, who was letting me live rent-free in the upstairs of her house, and who would have to get herself up at dawn the next morning in order to help my disabled dad get ready for work, was hardly ready to indulge my angst about fulfillment.