Still unsure of where I hoped to land, I typed up letters of introduction and
sent them to people all over the city of Chicago. I wrote to the heads of
foundations, community-oriented nonprofits, and big universities in town,
reaching out specifically to their legal departments—not because I wanted to do
legal work, but because I figured they were more likely to respond to my résumé.
Thankfully, a number of people did respond, inviting me to have lunch or come
in for a meeting, even if they had no job to offer. Over the course of the spring
and summer of 1991, I put myself in front of anyone I thought might be able to
give me advice. The point was less to find a new job than to widen my
understanding of what was possible and how others had gone about it. I was
realizing that the next phase of my journey would not simply unfold on its own,
that my fancy academic degrees weren’t going to automatically lead me to
fulfilling work. Finding a career as opposed to a job wouldn’t just come from
perusing the contact pages of an alumni directory; it required deeper thought and
effort. I would need to hustle and learn. And so, again and again, I laid out my
professional dilemma for the people I met, quizzing them on what they did and
whom they knew. I asked earnest questions about what kind of work might be
available to a lawyer who didn’t, in fact, want to practice law.
One afternoon, I visited the office of a friendly, thoughtful man named Art
Sussman, who was the in-house legal counsel for the University of Chicago. It
turned out that my mother had once spent about a year working for him as a
secretary, taking dictation and maintaining the legal department’s files. This was
back when I was a sophomore in high school, before she’d taken her job at the
bank. Art was surprised to learn that I hadn’t ever visited her at work—that I’d
never actually set foot on the university’s pristine Gothic campus before now,
despite having grown up just a few miles away.
If I was honest, there’d been no reason for me to visit the campus. My
neighborhood school didn’t run field trips there. If there were cultural events
open to the community when I was a kid, my family hadn’t known about them.
We had no friends—no acquaintances, even—who were students or alumni. The
University of Chicago was an elite school, and to most everyone I knew growing
up, elite meant not for us. Its gray stone buildings almost literally had their backs
turned to the streets surrounding campus. Driving past, my dad used to roll his
eyes at the flocks of students haplessly jaywalking across Ellis Avenue, wondering
how it was that such smart people had never learned to properly cross a street.
Like many South Siders, my family maintained what was an admittedly dim
and limited view of the university, even if my mom had passed a year happily