How Michelle Obama handled falling in love at work

Still smitten.
Still smitten.
Image: Reuters/Jim Bourg
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In 1989, Michelle Obama was a 25-year-old junior associate at a prestigious Chicago law firm when she experienced an existential work crisis, one she describes in detail in her captivating new memoir, Becoming (Crown, 2018).

The trouble started with an ordinary office request, as she writes:

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.

That intern, of course, is a 27-year-old Barack Obama, a first-year law student years away from becoming the US president.

Like 10% to 20% of married Americans (surveys vary), the former first couple met at work, and in Becoming, Michelle deftly explains how she navigated that situation, one that she clearly would not have chosen for herself. When they met, pragmatic Michelle, at that time Michelle Robinson, had sworn off dating entirely, making work her priority.

But the hold she describes, the one that’s starting to slip, has nothing to do with her stance on dating. Rather, she’s referencing the astoundingly accomplished, comfortable, but predictable life she has built for herself as a young adult. Besides an academic prowess that would land her at Princeton University and later Harvard Law School, what brought her to this moment in 1989 at the Sidley & Austin law offices, where she worked in the marketing and intellectual property group, is what she calls an affinity for “box checking.” She explains the recurring theme here:

I was a box checker—marching to the resolute beat of effort/result, effort/result—a devoted follower of the established path, if only because nobody in my family (aside from [my brother] Craig) had ever set foot on the path before.

Unlike the incoming summer associate, she had not taken time off to work between college and law school. When he arrives in her life, she is already successful, assigned to an office in a tower she used to admire as a child growing up in a largely working-class neighborhood on Chicago’s South Side. From her desk, she had a view of the lake, and could see a sliver of her old neighborhood. “Is there anything to question? It doesn’t seem that way,” she writes.

But with Barack’s appearance, the questions begin to gather.

A troubling lack of clarity

First comes her skepticism about this rumored-to-be exceptional character who landed a summer job a year earlier than most law school students. She’s prepared not to be impressed. “In my experience, you put a suit on any half-intelligent black man and white people tended to go bonkers. I was doubtful he’d earned the hype,” she writes. She certainly isn’t knocked off her feet by him, not right away. In fact, she attempts to set him up with a friend. But eventually, the friendship expands and deepens and they find themselves in a daily ritual, touching base to chat at the end of the day, drawn to each other.

Next we witness the relationship crossing a border into romance: We see the charismatic couple at the movie bumping into senior partners, at a company event they together ditch, and sharing an ice cream on a curb in Hyde Park. Thus the Obamas find themselves in a situation that will be familiar to the more than one third of Americans: they need to be inconspicuous about their new status at the office.

For Michelle, the situation is worrisome. She writes that she found herself “arguing silently with myself. Was there a way to do this unseriously? How badly could it hurt my job? I had no clarity about anything—about what was proper, about who would find out and whether that mattered…”

Even by today’s standards, where companies have established clearer rules about disclosing relationships and prohibiting dating between managers and their direct reports, the Obamas’ situation was not complicated. As Barack would point out, Michelle was not his boss. Her job as a mentor to him to was to make sure he felt socially connected—not that he needed any assistance there, she learned. And he would be leaving the firm at the end of the summer to return to Harvard.

He apparently had to make his case several times, Michelle writes in the memoir, calling him “a deadly combination of smooth and reasonable.” She continues:

More than once in the coming days, he laid out the evidence for why we should be going out. We were compatible. We made each other laugh. We were both available, and furthermore we confessed to being almost immediately uninterested in anyone else we met. Nobody at the firm, he argued, would care if we dated. In fact, maybe it would be seen as a positive. He presumed that the partners wanted him to come work for them, eventually. If he and I were an item, it would improve the odds of his committing.

“You mean I’m like some sort of bait?” I said, laughing. “You flatter yourself.”

What’s more, around the law firm, the response from Michelle’s colleagues was warm, which fits with what little research exists on the topic. “When workplace romances happen because of a love motive, all the studies show that colleagues react very positively to that,” Harvard Business Review’s Alison Beard explains in a recent episode of Harvard Business Review’s Dear HBR podcast. “Individual productivity goes up. Job satisfaction goes up for the people involved and their commitment to the organization increases.”

More compelling than the reaction of colleagues to the Obamas’ budding romance, however, is how the young lawyer grapples with the experience internally.

A wholesale change in careers

The launch of an office romance would be only one of many pivotal changes in Michelle’s life around that period. She also loses Suzanne Alele, her dear friend from Princeton, to cancer, and soon after loses her father, Fraser Robinson, to complications from his multiple sclerosis.

The sense that “life was short and not to be wasted,” as she later writes, became shockingly obvious following the death of these loved ones. The law, a profession she admits she was partly drawn to because of the looks of approval she received from other people when she declared it as her goal, suddenly wasn’t enough for her.

It feels inevitable that Michelle would have begun examining her life this way eventually, even if she hadn’t met Barack, but he was there, too—an unmissable model of an alternative way of living. He followed his inner compass rather than any well-worn route to wealth or status. Michelle writes:

What struck me was how assured he seemed of his own direction in life. He was oddly free from doubt, though at first glance it was hard to understand why. Compared with my own lockstep march toward success, the direct arrow shot of my trajectory from Princeton to Harvard to my desk on the forty-seventh floor, Barack’s path was an improvisational zigzag through disparate worlds.

After some soul searching, she would leave corporate law, where she had been considered a future partner, and take a job at Chicago city hall as an assistant to the mayor, the first step in a new career devoted to public service and community organizing. The transition was a process. She had spent several months contemplating the right move for herself, investigating possibilities at schools and nonprofits, networking outside of her field, making lists of the issues that moved her, speaking to mentors, and weighing the potential budgetary impact of switching tracks.

She looks back at that era with the benefit of age and quotes two lines from her diary: “One, I feel very confused about where I want my life to go. What kind of person do I want to be? How do I want to contribute to the world? Two, I am getting very serious in my relationship with Barack and I feel that I need to get a better handle on myself.”

As she reads the diary in the present, she sees her personal struggle, and her solution; she sees “what a no-nonsense female mentor might have said to me directly,” she writes.

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.

She longed for a job that would resonate for her, and she wanted to maintain her individual integrity while uniting with a powerful personality. She had “wanted to feel whole,” she writes, so she entered community service, and she would, in time, have a platform to urge millions of young Americans to do the same.