Permission to Swerve

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By embracing change and learning to listen to her inner voice, Valerie Jarrett has forged a life of purpose and fulfillment.

by JackieKrentzman

In her new memoir, Finding My Voice: My Journey to the West Wing and the Path Forward, Valerie Jarrett, former senior adviser to President Barack Obama, describes being in her twenties and envisioning a straightforward 10-year plan for her life.

1. Graduate from Stanford
2. Graduate from Michigan (law school)
3. Discover my career passion
4. Fall in love and marry
5. Have a baby
6. Be a fulfilled, satisfied, and happy wife and working mom

She began tackling the list and checking off each item. After graduating from Michigan Law in 1981, Jarrett began working at a prestigious law firm in Chicago. She had an office on the 79th floor of the Sears Tower with a breathtaking view. A few years later, she was married with a baby girl. The plan was working.

Yet, something didn’t feel right. Number six on her list wasn’t happening.
So when she reached 30, Jarrett took stock and realized she needed to leave her marriage and find a new career path.

That came from an unexpected place—City Hall. A mentor invited her to join the legal team in Mayor Harold Washington’s administration. In 1987, not without trepidation, she took the plunge (and a plunging pay cut as well).

Immediately, Jarrett knew she had found her career passion: public service.
Today, Jarrett is no longer a fan of 10-year plans or life checklists. She advises women who feel stuck to step back, take stock, and, if possible, make changes.

“I’m not saying that it is easy, particularly if you have the type of personality I had, in that once I made a plan I liked to complete it,” she says. “But I think it’s important that we are all are willing to do gut checks and not be wedded to a plan that is not working. When my plan stumbled, that is actually when the adventure began!
“If you have the good fortune to have a choice, you can keep trying to do what you have always done, or you can listen to the most important voice—the voice inside of you. Listen to it, and give yourself permission to swerve.”

By finding her voice, trusting her gut, and embracing the journey, Jarrett has lived a series of beautiful swerves. She held several senior-level positions in the mayor’s office in two administrations (Washington died suddenly in office in 1987, and Richard Daley was elected). There she learned the nuts and bolts of public administration, and also realized the vicissitudes and messiness inherent in governing with stakeholders who have disparate and competing agendas. In 1991, she was shocked when Daley asked her to serve as his deputy chief of staff. In that position, she toggled between an insider’s and a public-facing role, skills that would later serve her well in the White House.

Jarrett continued to forge a satisfying career in Chicago, serving as the chair of the Chicago Transit Board and the commissioner of planning and development. She figured she was back on her path, albeit with more self-knowledge and an openness to change.

She had no idea how profoundly her life would change when in 1991 she interviewed Michelle Robinson, a recent Harvard Law School grad and a Chicago native, for a job.

Soon, Jarrett, Robinson, and Robinson’s fiancé, a community organizer and also a young Harvard Law grad named Barack Obama, became fast friends and lived three blocks apart. Jarrett connected with Barack on many levels, including having lived outside the United States. He spent part of his childhood in Indonesia; Jarrett spent the first five years of her life in Iran, where her father was the chief of pathology at a hospital. As a victim of ingrained Jim Crow practices, he couldn’t find a commensurate job in Chicago despite his sterling qualifications.

Both Jarrett and Obama, as outsiders, instinctively had the ability to draw out someone’s personal story and journey, and to find commonalities—a trait, she notes, that is of utmost importance today in our oft-fractured and polarized society.

Jarrett learned another valuable lesson from her early years outside the United States: she discovered it was challenging to fit in at school when her family returned to Chicago. She got teased mercilessly, for her accent, her clothes, or whatever difference children manage to find. In later years, she recognized that this “othering” she experienced, coupled with her determination to fit in at all costs, was one of the factors that kept her from accessing her voice and authenticity.

“I regret I that I spent so much of my childhood trying to be like everybody else,” she says. “I do think it’s normal. I think kids are more likely to get bullied if they do not conform.”

Even though she tried to blend in, Jarrett says, she was bullied anyway. “That is why, when I was in the White House, I was a strong advocate for ending bullying. I knew how it made me feel.”

That was just one of her lived experiences Jarrett brought to the White House. When Obama was elected president in 2008, he asked Jarrett to serve as his senior adviser and assistant for public engagement and intergovernmental affairs. She had the latitude to build a portfolio around issues that she was passionate about and which, in many cases, resonated personally. These included efforts to champion equality; fight sexual assault; raise the minimum wage; support early childhood education; and advocate for workplace policies that support working families. The connective tissue among the initiatives was advocating for those whose circumstances were a barrier to getting their voice heard.
Once again, this instinct hearkens back to her childhood experiences.

“I started my life very shy, painfully shy, and it was not until I was a young adult that I really learned how to use my voice to be a force for good,” she says. “It was easier for me to advocate for somebody who I felt did not have a strong voice. When I had been practicing in the private sector, I was advocating for clients who already had a big voice. I was just there to help make sure that they dotted the i’s and crossed the t’s. Their voice did not need amplification. So when I swerved into public service and there was something about being a part of a mission bigger than myself, I learned how to speak up.”

In some cases, speaking up meant persuading the president and holding him accountable. Her closeness to Obama, his respect for her, and her comfort level in pushing back at times helped earn her the nickname “The Obama Whisperer.”

In many respects, the White House is like a large corporation, with the president as the CEO. Jarrett says that, as in a company, the role of Obama’s White House team was to help advise the president to make sure he made the most informed decisions possible. As she knew him so well, sometimes it fell to her to make the hard asks and challenge his thinking.

One example occurred in the first year of the Obama administration. Jarrett noticed that women in the White House, including those in senior leadership positions, were reluctant to voice their views in meetings. These meetings were often heated and confrontational, and women were not wading into the fray. She also noticed that these same women spoke their minds when Obama was in the room, as he encouraged them to participate. But when he wasn’t in the room, they tended to shrink back, and the men dominated the discussion.
So she spoke to Obama about what she saw. To his credit, he understood that it was his responsibility to shape the workplace culture and to ensure that every voice was heard. When he asked her advice on how he could change these dynamics, she suggested that he host a dinner for these women in the White House family residence—which was less intimidating than the Oval Office.

“I think the fact that he stepped right in and said to the women, ‘Share with me what’s going on here and I want to be a part of the solution,’ made all the difference,” Jarrett says. “The other thing he said at the dinner was, ‘Look, I know it’s hard to speak up. I know we all have pride and sometimes we can all get shut down [by others in the meeting]. You can’t afford to take it personally. I need you to speak up. I need your voice in the decision-making process. I will make better decisions with the benefit of what you have to offer.’ That was an incredibly empowering thing to say to the women in the White House.”

In Finding My Voice, Jarrett explores not only why unearthing her voice was foundational for her, but what it means for women in the workplace—or home or community—to feel comfortable expressing themselves. In today’s workplace, women, especially women of color, can struggle to find the right balance between bringing their authentic selves to the job and suppressing a part of their selves, to give them a better chance of landing—and keeping­—a job.

Jarrett understands the tendency to do whatever it takes to fit in to a particular culture, but she encourages women to bring their full selves to the table—not only for their own sake, but because it enriches the community as a whole. “We need to have the courage to share our whole authentic self, knowing that it is a strength to the organization,” she says. “I encourage women of color to speak up. Sometimes it’s scary, and intimidating. You wonder if you’ll be accepted. But the way I look at it, you are actually doing the enterprise a favor because you will ask different questions than people who don’t look just like you.”

Jarrett also counsels women to not be hesitant to inquire about a company culture during the interview process.

“When you are in the interview process, ask tough questions to make sure you are going to be able to thrive in that environment and to make sure you are going to be able to be your whole self. Interviewing is a two-way street. Oftentimes we’re so busy trying to sell ourselves that we forget that we are a buyer. It is better to ask those questions at the front end and find out what kind of culture you are walking into than to get there and realize, ‘Oh, I have a whole part of my life I have to leave behind in order to fit in here.’”

Today, three years from serving in the White House, Jarrett hasn’t slowed down. She is a senior adviser to the Obama Foundation and a senior distinguished fellow at the University of Chicago Law School. She also serves on the boards of Ariel Investments, 2U, Lyft, the John F. Kennedy Center for the Performing Arts, and the Economic Club of Chicago.

Jarrett identifies three current projects that are the most meaningful, in large part because they allow her to do what she does best—advocate for those whose voices have been suppressed, through generations of institutional racism and exclusion or through other circumstances.

The first is the nonprofit campaign When We All Vote, whose mission is to increase voter participation. When We All Vote was launched in 2018 by Michelle Obama, Tom Hanks, Lin-Manuel Miranda, Janelle Monae, Chris Paul, Faith Hill, and Tim McGraw. Jarrett, Tina Tchen (director of the White House Office of Public Engagement under Obama), and political consultant Pete Rouse serve as cochairs.

“The reason why voting became front and center [for me] is that we looked at the data after the last presidential election and learned that 43 percent of eligible Americans did not vote in the presidential race,” she says. “And we were finding this pattern not just in the presidential race. Voting in every race matters. Who is your state’s attorney making decisions about who to prosecute? It matters who’s on your city council deciding the budget and the priorities in your city, and it matters who is in your state legislature drawing maps that determine whether your voice really matters in elections. Certainly it matters who’s in Congress.”

Another initiative is the United State of Women (USOW), which she cochairs with Tchen. USOW is an outgrowth of the Obama administration’s White House Council on Women and Girls, which Jarrett cochaired and for which Tchen served as executive director. USOW advocates for gender equity, equal pay, and workplace flexibility, among other priorities, through several programs, including a biannual summit (with regular regional iterations) and an Ambassador Program that deploys women leaders in the field, working closely with nonprofits and regional and local governments.

Once again, this project is personal. “I did not speak up for myself when I was a young working mom, and I want to empower other working moms to do so,” Jarrett says.
The project that may be nearest and dearest is the Obama Presidential Center. The center will celebrate President Obama’s and Michelle Obama’s legacy. It will also help revitalize Chicago’s South Side by creating thousands of jobs, sponsoring programs for children and adults in the community, and bringing millions of visitors to this historically impoverished neighborhood.

Jarrett is involved in many aspects of the center, including fundraising, planning the building’s physical structure, and programming. “I think the center will be both an economic engine and a beacon of hope in Chicago,” she says. “The president will have an opportunity to continue to teach best practices about civic engagement and how to get people, particularly young people, to feel a responsibility to be a force for good.”
Today, more than 30 years after she left the legal fast track, Jarrett can look back with satisfaction at her journey. Her ability to swerve was instrumental in finding her purpose. So was her openness to embrace its close cousins, the zig and the zag. How could she have anticipated that her best friends would one day be the most powerful couple, arguably, in the world?

By recognizing opportunities and trusting her heart and inner voice, Jarrett shaped a life that has provided her with abundant purpose and fulfillment. At the same time, she recognizes that life is always a work in progress and nothing can be taken for granted.
When asked for a lesson she learned at the White House that can be applied to working women everywhere, she had a ready reply. “I learned the importance of recognizing that no matter how high we go, we have to work hard to use our voice to be that force for good—even if it is uncomfortable. And, by doing so, you will not only be a force of good for others, but be a force of good for yourself.” DW

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