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Michelle Obama Shares Her Chicago Lessons

Transcript of interview follows essay.

At her core, Michelle Obama is a girl from the South Side of Chicago. And so are her people.

The former first lady has always talked lovingly of her working-class roots and salt-of-the-earth parents in South Shore. Like many black Chicagoans, Obama hails from the Great Migration, which left an indelible mark on the city and all its people. Her life and her perspective have been shaped by the city’s deep legacy of race, segregation and inequality.

Growing up, her life teemed with backyard barbecues, bid whist and sounds of Stevie Wonder. Riding in her dad’s Buick Electra 225 provided simple and joyful memories. She enjoyed a big extended local family with cousins, uncles and aunts -- including one who was a hard-edged music teacher and taught her piano at age four.

Obama’s grandfather Southside rigged a makeshift turntable sound system to blast jazz. She told me her other grandfather Dandy “was a postal worker and was frustrated with the limitations race put on his abilities because he was a brilliant man... frustrated with as smart as he was, he could only rise as high as the post office.”  

I talked with Obama on the eve of the release of her much-anticipated memoir Becoming. I interviewed her in a computer lab at Whitney Young Magnet High School, her alma mater, where she spent the afternoon with 20 female high school seniors. She hugged each of them. They squealed with delight and listened aptly as she gave them advice on college essays and belonging.

Already excerpts of Becoming resonate -- fertility struggles, opening up about seeking marital counseling, never forgiving President Donald Trump for his birtherism claims against her husband. The first black First Lady who time and time again had to fight off the Angry Black Woman trope.

She’s not only the descendant of the Great Migration, but of enslaved people. Obama writes about the hurt, anger and lessons she learned as a political wife on the campaign trail and in the White House. The book is warm and beautifully written, but I wanted to spend my limited time understanding the place -- the South Side -- that shaped her, and someone like me.

It starts with school, segregation and white flight. In the 1960s, a young Michelle Robinson attended Bryn Mawr, a public neighborhood elementary school. In kindergarten, her class was racially diverse. By eighth grade, there were no white kids.

“The pernicious fear of black people like us moving into the neighborhood and the neighborhood becoming a ghetto. Those weren’t things that I thought about at the time. But you could feel it. I could feel it in my classrooms. I could feel sort of a change,” Obama said.

When the star student got accepted into Whitney Young, she questioned whether she was good enough to compete. She thought maybe she wasn’t meant to be there. Obama again felt the same way when she enrolled at Princeton University. That nagging question persisted: do I belong here?

“It took awhile,” Obama told me when I asked how she pushed through. “So I landed on this campus. Princeton is one of the most ivy of the Ivy Leagues. Very wealthy. Very elite. Kids arriving to campus in limousines. For me, I tried to recreate a community of comfort for myself.”

She describes herself as a poppy seed in a sea of whiteness.

Obama, ever the pragmatic and box checker, no doubt influenced by being a first-generation college graduate, completes Harvard University Law School. She lands a job as a corporate lawyer, upwardly mobile, living a content buppie life in Chicago. But it left her unfulfilled. Turns out, she never wanted to be a lawyer; it’s what she thought she was supposed to do. So she learned to “swerve,” as she calls it, in part by meeting bookish Barack Obama, a young upshot who didn’t care about material things and measured success in a nontraditional path. She’d look over at him staring at the ceiling and find out he was contemplating income inequality.

Let’s be clear, she doesn’t hand over her agency to Obama. She could teach a master class in marriage for wives with young families that makes you want to pass a collection plate.

In describing a rough patch in their marriage, Obama took control over her happiness. “I learned how to keep moving forward and not waiting for husband. And I wanted to teach that to my girls, as well. You move forward in your life as a woman. You have power and agency to define your life outside of the man in it. That was an important turning point for me.”

I asked her what was hardest about writing this book and whether she allowed herself to be vulnerable.

“Over the years, I’ve become comfortable and proud of my entire life. Not just the high points but the bumps and the bruises,” Obama said. “It’s also important as someone who’s viewed as a role model to young people that they get the whole truth. I just don’t think it’s fair for us to sit on our role model pedestals and pretend like this was easy or that we didn’t struggle. Kids need to hear, yes I failed the bar the first time. Michelle Obama failed something. Michelle Obama feels hurt. Michelle Obama feels fear. The hope is that gives so many others the permission to feel those feelings and to know it’s not the end of the world, it’s part of that journey of becoming.”

As a South Side girl myself, that’s a message that many young black women in Chicago long to hear. It’s a pick-me-up that confirms our value, reminds us of our gifts, and emboldens us to press on after we’ve fallen. Though our city offers many hard lessons and produces many unfair realities, Obama stands as a symbol of what’s possible for all South Side girls.

TRANSCRIPT

Michelle Obama: We are people of Chicago on both sides of my family. We have southern roots. South Side. My maternal grandfather was from Alabama and Dandy, who's my paternal grandfather, came from South Carolina. So like most Chicagoans, our roots were in the south.

Natalie Moore: As a child you notice the transformation of your neighborhood -- white flight, segregation. How did that shape our impact your identity as a black South Side girl?

Obama: You know I didn't realize what was happening when I was young. I was only reflecting back over the years that I realized what was going on that slowly, literally the white people in my life were disappearing overnight. And I put in two pictures in the book of just to show the stark difference of my kindergarten class or first grade class. It's a very diverse picture. You know we had Mexican kids ... South Korean kids and I mean it was a mixture of everything. By eighth grade in that same school there were no white kids. I would come to realize that they were all moving south because of you know the pernicious fear of black people like us moving into the neighborhood and the neighborhood becoming a ghetto. And now again those weren't things that I thought about at the time but you could feel it.

Moore: We're sitting in Whitney M. Young (Magnet High School) right now and I remember reading you talk about wondering if you belonged here. The same with Princeton. How did you work through that self-doubt and say you know what I do belong here?

Obama: So I landed on this campus of Princeton is one of the most Ivy of the Ivy League very wealthy very elite. You know for me what I did was I tried to recreate a community of comfort for myself and I did that by pretty much staying very close to the black community that was there. It was a place of comfort for me in this bastion I call it. I was a poppy seed in a sea of whiteness. But this isn't something that I encourage kids to do what I did. You know I kind of just stayed with my community and I think I missed out on a lot.

Moore: So then you got to Harvard Law School you're a corporate lawyer you're living in upwardly mobile buppie life, happy hours, but you didn't feel fulfilled in you used this term a lot in the book: when someone takes a swerve. What was your swerve?

Obama: Whoo! I think my first swerved I had many words I learned to swerve the White House was probably my biggest swerve politics with my husband was a big, huge swerve. But the first babies were was sort of recognizing that I had been building my life up until that point based on things I thought I was supposed to do. So I had landed a wonderful job as a lawyer in a big corporate firm but I didn't want to be a lawyer and I had never taken time to think about why I was going to law school. That was just the next step. And meeting Barack Obama and falling in love with him and having somebody in your life that you cared about that influenced you and encouraged and encouraged you to take some risks and helped me begin to start my swerve and to leave the law and to start going into public service and working for the government. But I don't think I would have had the courage to completely do that as quickly as I did without him.

Moore: Work life balance is something that women before you have struggled with women after you are going to continue to struggle with. But at one point in your marriage you thought about your own agency and creating your own
happiness. What was that like?

Obama: One of the things I learned in marriage is that two individuals leading separate lives and coming together you know when important and necessary and when there's time works really well until you have kids. We were starting to
feel that rub and we needed to take a moment to kind of think about you know how we got here and what we're going to do over the course of our counselling one of the things I learned through counseling was that I was responsible for my happiness. You know first and foremost Barack can love me but I have to decide in my life what I want and I can't wait for permission from him or even his agency to help me do it.

Moore: What was the hardest thing about writing this book. How vulnerable did you allow yourself to be on the pages.

Obama: You know I am a pretty open book. Over the years I've become comfortable and proud of my entire life. Not just the high points but the bumps and the bruises; I've had to learn how to make sense of all of that in order to get to this place. So for me that process is part of the story. I also think it's important as someone who's viewed as a role model to young people that they get the whole truth I just don't think it's fair for us to sit on our role model pedestals and pretend like this was easy or that we didn't struggle. You know kids need to hear, 'Yes I failed the bar the first time.' Take that in everyone: Michelle Obama failed something. You know? Michelle Obama feels hurt Michelle Obama feels fear you know and the hope is is that that gives so many others the permission you know to feel those feelings and to know it's not the end of the world that it's part of that journey of becoming.


 is WBEZ’s South Side reporter. You can follow her on Twitter.


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