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.

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