Valerie Jarrett's leap of faith that started her path to the Obama White House

Salon talks to the former senior adviser to President Obama about Michelle, public service and trusting herself

By D. Watkins

Editor at Large

Published June 26, 2019 3:00PM (EDT)

Valerie Jarrett (Salon Talks)
Valerie Jarrett (Salon Talks)

In 2008, lost me sat in the middle of a trap house (or "illegal drug distribution center," if you prefer) in the middle of a bunch of BGF (Black Guerilla Family) gang members. A small flat screen mounted over a makeshift table played “Fresh,” “Paid in Full,” or whatever hood movie we watched on repeat every day. At the time, I had retired from selling drugs. I was never in a gang, but these were my remaining childhood friends, the people I enjoyed smoking weed with the most.

My friend Free flicked through the channels, sick of watching the same movies all the time, and stopped on MSNBC. There I discovered the young senator from Illinois who was running for president. Barack Obama was a sharp, smooth politician — the only one I had ever connected with. My introduction to Obama and the way he spoke gave me a different type of hope, one that I never imagined. For the first time in my life, I had a vision of something to look forward to. I dug deeper into politics, read more about the issues our country faced, and said goodbye to wasting time blowing weed in trap houses. I truly wanted to make an impact and do something positive with my life.

In 2008, a driven and focused Valerie Jarrett was secure in her position as an advisor to soon-to-be president Obama. Jarrett was a believer, and had always been a believer, since she saw something special in a young lawyer named Michelle Robinson during an interview decades earlier.

Jarrett, who had been working in the Chicago mayor’s office, was infatuated with Robinson’s resume and recommendations. When she offered Michelle the job on the spot, she didn’t accept it initially because she wanted to talk it over with her fiancé.

“Who is this fiancé and why do we care what he thinks?” Jarrett wondered.

Jarrett later had dinner with the young couple and developed an immense respect for their relationship and how they made decisions together. It would give her career new purpose. She went on to work alongside the Obamas throughout their careers, joining the White House team on January 20, 2009, as senior adviser to America’s first black president. She stayed in the role longer than any presidential senior adviser in U.S. history.

Jarrett attributes much of her success to luck, something that so many people leave out of their come-up stories. It’s crazy how Jarrett, the great-granddaughter of the first black person to attend MIT, the granddaughter of a legendary architect who built one of the largest housing complexes in the world, and the daughter of a successful doctor in a family where it seemed like everyone went to college still needed luck to find her way.

She and I sat down together for a conversation on "Salon Talks" to discuss her journey and her new memoir “Finding My Voice,” in which she discusses her work ethic, her dedication to public service, and how she’s grappled with her family’s legacy and her love life along the way.

I'm drawn to your book title, “Finding My Voice,"  because regardless of race, gender and ethnicity, finding our voice is something that we all have in common. It's a constant journey and it's extremely important. How did you find your voice?

It took a while. I will say I grew up painfully shy, D, which is hard for people to believe now since I can't seem to stop talking. But back in the day, I was and I didn't really know what I wanted to do. And I was around a lot of people who had clear visions of their life, and I thought let me make one up myself.

And so I just made up an idea of what I wanted and a 10-year plan, and I looked up in 10 years and I was miserable. I thought I'll got right to college, then law school; I'll find my passion in the law. I'll fall in love, get married, have a baby by 30, and then live happily ever after. And I had executed on that plan, and my book begins sitting in my very fancy office in a big corporate law firm in Chicago, in a very unhappy marriage with a new baby, and I would just sit there and cry.

Can you talk about the pressure? You mentioned planning. It sounds like you're a Type-A personality and you want everything to happen a certain way. My grandma used to always say you can make a plan, but you can't plan the outcome.

That's exactly right. Wise lady. I think you make these plans and then they get very comfortable. And in my case, I was the first lawyer in my family, so my parents and everybody was very proud. So you start to think, okay, everybody thinks this must be great, I guess it's great. But the key is, and the key to beginning to find your voice, is to listen to the most important voice, and that's the voice inside of you. And the voice inside of me was saying this is not my calling.

Particularly, after I had my daughter, I went back to work and I'd leave her every day, and I'd say I'm leaving her and I'm doing something so completely unfulfilling. Mayor Harold Washington had just been re-elected Mayor of Chicago, first black mayor, and I had knocked on doors for his campaign. I was just like thousands of people across the city who fell in love with him, and for the first time felt really connected to the city. Before Harold Washington, I didn't know who my local alderman was—I probably didn't know how many aldermen there were. I didn't know anything about how the city worked because it didn't seem relevant to my life, but he made me feel like he was my mayor.

It’s crazy that you said you have to listen to yourself. In my experience, and I've had these fights with my friends, I feel like no one lies to you more than yourself. How did you beat that?

Well, this is how I felt about my marriage. I felt I can just will this to work. And if I just am accommodating, and try to be solicitous, and try to think of all the different ways that I could make this person respond to me the way I want them to, then I can make it happen.

We think we can change people.

What my grandmother says is, you cannot change a leopard's spots. They kind of are the way they are. You can work around the edges, but their basic core, I think in my case, I married the fantasy of who I thought my husband was. I had had a crush on him since I was eight and he was 12, and he didn't pay any attention to me at all until I was 25. And when he looked at me, I thought, "I'm going to marry you." So little thought went into such an important decision because I thought if I married somebody who looks good on paper and he will complete me, and he will make me happy.

He was a doctor.

He was a doctor like my father. Our moms grew up in the same apartment building. Our dads were friends. There was so much that made sense in terms of him being figuratively “the boy next door,” but I hadn't actually gotten to know him.

The question is are you being honest with yourself? Are you doing that gut check to say does that fantasy actually bear any resemblance to reality? I had this fantasy of a life, and I was getting a lot of positive reinforcement. My friends were so envious that I had this high-paying job and fancy office, and all this stuff. And what my friend who had worked for Harold Washington said, "Look, you need to feel like you're a part of something bigger and more important than yourself. Just simply working for these clients at the private law firm isn't fulfilling, so why don't you think about public service?"

And so I took this leap of faith, and everyone thought I was nuts because I took a cut in pay, my office had a window facing a cubicle facing an alley. It wasn't even an office. And I just said this is going to be right for me. And the worst thing that would have happened, D, is I could always go back to the law firm, right?

You could have always gone back to practicing law.

I think one of the other mistakes I made early on is that I also thought I was superhuman, a super woman. I was going to have it all as I defined it, which meant doing it all myself and never asking for any help. I did lie to myself about 'Oh, I have this, I have this.' Anytime anybody tried to help me, 'Oh no, I got it.' Meanwhile, balls are dropping all around me and things are a hot mess.

That's a common theme many women are now talking about—can you have that perfect relationship, can you have that perfect child, can you maintain that perfect career, can you go out to brunch with your girlfriends on Sunday and talk about how perfect everything is?

That's not life. I'm now at the stage just having written this book where I spent a lot of time looking back, and to me the question isn't did I have it all, was everything perfect? The question is did the multiple chapters add up to a whole life? Each one has tradeoffs. Each one has challenges.

I can remember when my daughter was young, I felt like to your point, if I were just smarter, more efficient, better organized, then I could do this. And there must be something wrong with me that this is so hard. It took me a while to realize no, no, no, it's just hard.

It was hard for me, with so much going for me, what about those working families that are doing two shifts at minimum wage with no safety net around them, and one paycheck away from bankruptcy if somebody gets sick or in an accident, or whatever might happen to you? It's part of what drove me when I was in the White House to try to advocate on behalf of those families that didn't have what I had. But the question I think I started to come to terms with is, look, I have to be more willing to open up and tell my story.

Was that difficult?

Very hard, very hard because I had to admit first of all to myself this marriage is actually not working. Okay, this fancy law firm is not fulfilling to me. And when my marriage broke up, I actually felt I was a failure. And it took me a while to realize, oh no, it just didn't work out, and you can't let your things that don't work define you as a failure as a human being. It just didn't work out. Nobody died. I think my message to young people particularly is don't set such high expectations for life because you can't possibly meet them, and then you'll be a disappointment to yourself. Be more adventuresome, and it's OK to fail, it's OK to stumble and fall.

I think you're extremely qualified to put that message forward, and I say this because you have a rich family legacy where everybody went to college and everybody took education seriously. I'm a first-generation high school graduate, so I didn't have those pressures. You saw what perfection looked like.

I did come from this family of high achievers, beginning with my great-grandfather who was the first African American to go to MIT, but his father was born a slave. And so I always think about how did his father, once he was freed, figure out I should save money and value education, and even think to know to send his son to MIT? Where did that even come from? And so it gave me confidence that trailblazing can work, and I became comfortable being the first person to walk in a door, whether I was a woman or a person of color. I also felt responsible for leaving the door open and helping other people come through it.

Were you aware of that powerful legacy when you first got into public service, or was it just something that you became aware of over the years?

I knew about it because my grandmother, Pudd'n, talked about it all the time, and she had photographs of all of these folks in my family on the walls of her home. And she would make me listen to these stories because she wanted me to appreciate where I came from, and that people had sacrificed for me to have opportunities that perhaps they didn't have, and that I needed to be mindful of that as well.

Then my parents reinforced the same thing. They used to always say, "You know what? You're black, you're a woman; you'd better work twice as hard. But even if you do, you have to be lucky. Just don't think because you're successful that there's something all that extraordinary about you, because a lot of people are just as hard working but the breaks don't fall their way.” All of that, I think, grounded me and gave me a safety net of love and support that I could take chances that a lot of people aren't in a position to take. And for them, I'm very grateful.

You held a number of positions in Chicago, beginning in the mayor's office. What are you most proud of in terms of your public service there?

This one's very personal. The Robert Taylor Homes, which at one point was the largest public housing development in the world, was named after my grandfather, who had been chairman of the Chicago Housing Authority. It was named after him about five years after his death. I remember going to the opening—I think I was about six at the time—and feeling this tension from my mother, and her sister, and her grandmother because my grandfather believed that public housing should be a part of the urban fabric, that it should be architecturally the same, and that families should be given the resources that they need to get back up on their feet. And it should be temporary, a temporary way station.

It should not be these high rises that isolate families without jobs, without good schools, without parks that are safe, without places to shop, where they're not food deserts where you can't get affordable food, but rather a part of the community. He resigned from the housing authority because he couldn't get the city council to allow him to build public housing throughout the city of Chicago.

When I was Commissioner of Planning and Development, I was responsible for overseeing the transformation plan, which was to tear down these large, dilapidated public housing developments and build back in mixed-income housing. I'm very proud of the work that we did on that. It wasn't perfect. We had to listen a lot, and there were often conflicting goals from the residents and the residents' lawyers. But in the end, our goal was to give people a better life. And I think that the ones that have come to play so far are successful. And we're building these mixed-income communities, which give the people in public housing the respect that they need, and that they aren't stigmatized for any reason whatsoever, because they're just trying to get a leg up, too.

I tell the story about a very special woman in the book who was not extraordinary. She lived in public housing. She moved in when Robert Taylor was first built. She raised her children there, sent them all to college, and that's not the story you hear on the nightly news. I wanted to be able to give those families the opportunity to live a good and decent life, and hopefully find the skills that they need to be upwardly mobile.

When you did tear those homes down, where do those families go?

That's a good question.

How does it work? The only reason why I'm asking is because I was in Chicago a couple of months ago and I felt like I had to drive 20 minutes to see some black people.

Where were you? Because I live about 10 minutes from the Loop.

I was downtown and I drove to the south side.

You shouldn't have had to have gone very far to see some black people! One of the downsides to the Chicago Housing Authority is that because so many of the units were uninhabitable, a lot of them were vacant, and so we were able relocate people in one building and tear down the second building. We were able to give people vouchers so that they could move out of the public housing into privately subsidized housing if that's what they wanted to do. And those who complied with their rent and were in good standing when the housing was built could move back in, but we made sure that it wasn't, because again, these high concentrations horizontally what we'd torn down vertically, we wanted to have an economic mix.

In your book, you also talk about your relationship with Michelle Obama, who was Michelle Robinson when you first met her in Chicago. The funny thing is, she ended up interviewing you for the position that you were interviewing her for.

She did turn the tables on me. She turned those tables in about 10 minutes flat.

Did you see parts of yourself in her?

I thought she was much more confident than I was at her age. She was about 27 at the time I interviewed her. She had been at a big law firm for a couple of years, so she figured out quicker than I did that it wasn't right for her. But she just was so over for her years. She was wise.

What she did that I did not do in the interviewing process is she wanted to make sure at the front end that it was a good fit, so she asked some very hard questions. And then after I gave her a job offer and she talked it over with her fiancé, neither of them were satisfied. So they were like, you need to come have dinner with us. And I respected that. I respected the relationship, the partnership that they were forming. When people have said to me ‘wasn't that odd that she wanted her fiancé there?’ and I have said that there wasn't a major decision he made in his career without Michelle Obama right there at the table with him.

So you show up to this dinner with Michelle and Barack and you're prepared to answer questions about the position, and he's like, "Uh, so you grew up in Iran?"

Yes, he went right there. And it used to always make me uncomfortable when people would say ... Because as a young child, I think I was kind of traumatized when we came back, when we came to the United States. For my parents, they were returning home. My dad had left with my mother because he couldn't get a job when he came out of the Army at a major teaching hospital comparable to his white counterparts. They had taken this huge leap of faith, gone all the way to Iran. He headed the department of pathology and started a new hospital in Shiraz, Iran, and I was the second baby born in that hospital. Then we went to London because of the research he did in Iran, and then he went into staff at the University of Chicago.

He would say sometimes that the shortest distance to where you want to go means you've got to be prepared to take the long way around. But I never used to like to talk about being born in Iran, even though at the time the United States had strong diplomatic relations with Iran, but it made me different. When my parents plopped me down in my public school, I had a British accent from that one year in Great Britain, and they'd say where are you from, and where is that country? I wanted to just be like everyone else.

When I had dinner that first night with Barack Obama and he said, "Well, where are you from?" I said, "Chicago." He said, "Did you grow up here?" I said, "Yes." He said, "Were you born here?" And I went, "No, I was born in Iran." And he said, "Oh, that's interesting." And then he told me about his life in Indonesia, and we saw that there was really a lot in common in terms of how we were raised outside of the country, the appreciation that gave us for the United States, and how we realized that the United States really is a part of a global world, and we're not the only country on Earth.

The first time I remember ever seeing you was back in 2008 on MSNBC.

Did I look terrified?

No, you didn't look terrified. It was a world that I didn't really understand. Obama was my entrance into politics.

Just like Harold Washington to me, huh?

Yeah, it was 2008, I'm selling crack. I got shot. I was in a whole different space. I had no jacket, no glasses. It was a different situation. And I'm here because of luck.


I'm here because I've had an opportunity to be able to understand some things outside of my own social context. But I'm also here because if I would have never left, then maybe I would have been in more trouble.


But I went right, and I was in less trouble. And I think it's unfortunate that we have to say that, but it's a hard truth that we have to say. I would like for you to speak to something that I also think is important as far as your career path goes, and that is, elevating the voices of women in the White House. Could you speak to that, and could you speak to some of the current movements we have going on right now with MeToo and Time's Up?

I think because when I worked for city government, where I truly found my voice in how to advocate for others, was in part because I had an African-American woman who was my mentor, and Lucille pushed me in more ways and supported me in more ways than I could ever possibly thank her for. And so I thought I want to be that person for other people because it made such a big difference in my life.

In the White House, I did notice that women's voices were shrinking a bit. And when I mentioned it to President Obama, he said, "Well, that's not the culture I want to have. I handpicked them all. Let's have a dinner and talk about it." At that dinner, everybody kind of said why they were feeling hesitant and a little intimidated, and he said, "Look, I value your perspective. I believe that diversity of ideas will make my administration stronger, and so you need to fight for me. It's not about you, it's about your ideas and how they will help me."

I think it was so incredibly liberating and empowering for him to do that, and because I had this pre-existing relationship with him, I knew the kind of culture he wanted to build. And the women who were there were bringing the baggage from where they'd been before, right, and they didn't know him that well. And I think at that dinner, it really began to send the important signal that I value you and I want you to speak up.

Thinking back to the Obama years, now we have the exact opposite in the White House. How do you feel about that? Does it change how you think about this country?

This is the thing about our democracy, is it is always a work in progress. And if we aren't vigilant, we can't just presume we will always take steps forward. We can take steps back, in fact, he said I want to make American great again, like go backwards. Well, you know what? Go backwards for black people, I don't think that's so good. Go backwards for women, I don't think that's so good. Go backwards for those people on the border, I don't think that that's so good.

What gives me optimism and hope is that as I have traveled around the country, and you mentioned for example the MeToo movement, the day after the inauguration, we saw the Women's March, millions of women who came out and were actively engaged in trying to send a strong message about how they felt about the new president. The young folks from Parkland who excited the country with a March For Our Lives, where again, millions of people all over the country protested this epidemic that we have. And not just in cities like yours and mine, but all over the country over gun violence.

The MeToo movement, Time's Up, the number of people who ran for office in the midterm elections, people of color, women—more women elected in Congress in history. Six women running for president, two black people running for president and a Latino.

It all says a lot about how our country is responding.

I think the election was a wake up call, and I think people realize 'I can't just presume.' 43 percent of eligible voters didn't vote. That's a travesty, but I don't read too much into it because Hillary Clinton did get the majority of the votes. She lost in three states by less than 100,000 votes, but what can we do to wake up that 43 percent?

Michelle Obama and I started a new organization called When We All Vote. It's non-partisan and we want to change the culture, particularly with young people who have the most to lose.

By D. Watkins

D. Watkins is an Editor at Large for Salon. He is also a writer on the HBO limited series "We Own This City" and a professor at the University of Baltimore. Watkins is the author of the award-winning, New York Times best-selling memoirs “The Beast Side: Living  (and Dying) While Black in America”, "The Cook Up: A Crack Rock Memoir," "Where Tomorrows Aren't Promised: A Memoir of Survival and Hope" as well as "We Speak For Ourselves: How Woke Culture Prohibits Progress." His new books, "Black Boy Smile: A Memoir in Moments," and "The Wire: A Complete Visual History" are out now.

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