Looking back on it, I’m sure I was only capitalizing on what felt like a rare opportunity to speak with a woman whose background mirrored mine but who was a few years ahead of me in her career trajectory. Valerie was calm, bold, and wise in ways that few people I’d met before were. She was someone to learn from, to stick close to. I saw this right away.
Before I left, she offered me a job, inviting me to join her staff as an assistant to Mayor Daley, beginning as soon as I was ready. I would no longer be practicing law. My salary would be $60,000, about half of what I was currently making at Sidley & Austin. She told me I should take some time and think about whether I was truly prepared to make this sort of change. It was my leap to consider, my leap to make.
I had never been one to hold city hall in high regard. Having grown up black and on the South Side, I had little faith in politics. Politics had traditionally been used against black folks, as a means to keep us isolated and excluded, leaving us undereducated, unemployed, and underpaid. I had grandparents who’d lived through the horror of Jim Crow laws and the humiliation of housing discrimination and basically mistrusted authority of any sort. （Southside, as you may recall, thought that even the dentist was out to get him.） My father, who was a city employee most of his life, had essentially been conscripted into service as a Democratic precinct captain in order to even be considered for promotions at his job. He relished the social aspect of his precinct duties but had always been put off by city hall cronyism.
And yet I was suddenly considering a city hall job. I’d winced at the pay cut, but on some visceral level I was just intrigued. I was feeling another twinge, a quiet nudge toward what might be a whole different future from the one I’d planned for. I was almost ready to leap, but for one thing. It wasn’t just about me anymore. When Valerie called me a few days later to follow up, I told her I was still thinking the offer over. I then asked a final and probably strange question. “Could I please,” I said, “also introduce you to my fiancé?”
* * *
I suppose I should back up here, rewinding us through the heavy heat of that summer, through the disorienting haze of those long months after my father died. Barack had flown back to Chicago to be with me for as long as he could around my dad’s funeral before returning to finish at Harvard. After graduation in late May, he packed up his things, sold his banana-yellow Datsun, and flew back to Chicago, delivering himself to 7436 South Euclid Avenue and into my arms. I loved him. I felt loved by him. We’d made it almost two years as a long-distance couple, and now, finally, we could be a short-distance couple. It meant that we once again had weekend hours to linger in bed, to read the newspaper and go out for brunch and share every thought we had. We could have Monday night dinners and Tuesday, Wednesday, and Thursday night dinners, too. We could shop for groceries and fold laundry in front of the TV. On the many evenings when I still got weepy over the loss of my dad, Barack was now there to curl himself around me and kiss the top of my head.
Barack was relieved to be done with law school, eager to get out of the abstract realm of academia and into work that felt more engaging and real. He’d also sold his idea for a nonfiction book about race and identity to a New York publisher, which for someone who worshipped books as he did felt like an enormous and humbling boon. He’d been given an advance and had about a year to complete the manuscript.
Barack had, as he always seemed to, plenty of options. His reputation—the gushing reports by his law school professors, the New York Times story about his selection as president of the Law Review—seemed to bring a flood of opportunity. The University of Chicago offered him an unpaid fellowship that came with a small office for the year, the idea being that he’d write his book there and maybe eventually sign on to teach as an adjunct professor at the law school. My colleagues at Sidley & Austin, still hoping Barack would come work full-time at the firm, provided him with a desk to use during the eight or so weeks leading up to his bar exam in July. He was now also considering taking a job at Davis, Miner, Barnhill & Galland, a small public interest firm that did civil rights and fair housing work and whose attorneys had been aligned closely with Harold Washington, which was a huge draw for Barack.
There’s something innately bolstering about a person who sees his opportunities as endless, who doesn’t waste time or energy questioning whether they will ever dry up. Barack had worked hard and dutifully for everything he was now being given, but he wasn’t notching achievements or measuring his progress against that of others, as so many people I knew did—as I sometimes did myself. He seemed, at times, beautifully oblivious to the giant rat race of life and all the material things a thirtysomething lawyer was supposed to be going after, from a car that wasn’t embarrassing to a house with a yard in the suburbs or a swank condo in the Loop. I’d observed this quality in him before, but now that we were living together and I was considering making the first real swerve of my life, I came to value it even more.
In a nutshell, Barack believed and trusted when others did not. He had a simple, buoying faith that if you stuck to your principles, things would work out. I’d had so many careful, sensible conversations at this point, with so many people, about how to extract myself from a career in which, by all outward measures, I was flourishing. Again and again, I’d read the caution and concern on so many faces when I spoke of having loans to pay off, of not yet having managed to buy a house. I couldn’t help but think about how my father had kept his aims deliberately modest, avoiding every risk in order to give us constancy at home. I still walked around with my mother’s advice ringing in my ear: Make the money first and worry about your happiness later. Compounding my anxiety was the one deep longing that far outmatched any material wish: I knew I wanted to have children, sooner rather than later. And how would that work if I abruptly started over in a brand-new field?
Barack, when he showed up back in Chicago, became a kind of soothing antidote. He absorbed my worries, listened as I ticked off every financial obligation I had, and affirmed that he, too, was excited to have children. He acknowledged that there was no way we could predict how exactly we’d manage things, given that neither of us wanted to be locked into the comfortable predictability of a lawyer’s life. But the bottom line was that we were far from poor and our future was promising, maybe even more promising for the fact that it couldn’t easily be planned.
His was the lone voice telling me to just go for it, to erase the worries and go toward whatever I thought would make me happy. It was okay to make my leap into the unknown, because—and this would count as startling news to most every member of the Shields/Robinson family, going back all the way to Dandy and Southside—the unknown wasn’t going to kill me.
Don’t worry, Barack was saying. You can do this. We’ll figure it out.
* * *
A word now about the bar exam: It’s a necessary chore, a rite of passage for any just-hatched lawyer wishing to practice, and though the content and structure of the test itself vary somewhat from state to state, the experience of taking it—a two-day, twelve-hour exam meant to prove your knowledge of everything from contract law to arcane rules about secured transactions—is pretty much universally recognized as hellish. Just as Barack was intending to, I had sat for the Illinois bar exam three years earlier, the summer after finishing up at Harvard, submitting myself beforehand to what was supposed to be a self-disciplined two months of logging hours as a first-year associate at Sidley while also taking a bar review class and pushing myself through a dauntingly fat book of practice tests.