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Embrace the Zigzag: Valerie Jarrett on Taking Career Detours

It's all about learning to be comfortable when you're uncomfortable.

By imassimo82/Shutterstock
By imassimo82/Shutterstock

Serving as a senior advisor to the President of the United States and writing a bestselling book about the experience was never Valerie Jarrett’s goal. Neither was becoming a CEO, founding a non-profit or being named a boardmember multiple times over. But that’s exactly where she ended up, all thanks to the decision to deviate from her original career path and walk away from a prestigious position at a highly-respected law firm to pursue her passion for civil service. Needless to say, Jarrett doesn’t put much stock in rigid plans anymore.

“I thought that once you start a job… you should will it to work. Sometimes, though, that’s not possible,” Jarrett said. “My family and friends were really proud and impressed by this fancy office and big salary that I had, but it wasn’t rewarding to me. And when I took that pivot into local government for the city of Chicago, it changed my life completely.”

Jarrett largely credits her life-changing leap of faith to finally listening to what was inside her all along: “I had to learn to listen to the most important voice — the quiet one inside of all of us that we all too often ignore,” Jarrett explained.

In the latest episode of Glassdoor’s podcast, IN PURSUIT, Jarrett discusses her career journey, her work within the Obama administration and her choice to embrace her authentic voice with Glassdoor Editorial Director Amy Elisa Jackson. Read on for a few highlights, and download the episode to hear their full conversation.

Amy Elisa Jackson: When you look back at your career, what has surprised you the most about it?

Valerie Jarrett: How much sense it seems to make now, and how circuitous it seemed at the time. I did a lot of zigzags. I was always afraid when I made these big changes, and I didn’t appreciate that with that fear comes exhilaration and a sense of adventure. And now when I look back, each of the different steps added up to a whole life. When I was younger, I didn’t know how it was going to turn out, but it turned out pretty well.

Amy Elisa Jackson: I love the line in your book where you write that you wish you would have “embraced the thrill of the zig and zag rather than crave straight lines.” What do you think has been your best detour?

Valerie Jarrett: My smartest detour was leaving a big law firm. I was about six years out of law school in the middle of a bad divorce, and I had just had my daughter, Laura, not long earlier. Going back to work, I thought, “I’m leaving my daughter to do something that my heart isn’t in. Will she ever really be proud of me if I’m doing this?” The separation was getting to me and the work was getting to me, and I thought, “Let me do something that I care passionately about,” which meant I had to learn to listen to the most important voice — the quiet one inside of all of us that we all too often ignore. I think that that’s what I’d been doing. I’d been doing what seemed to make everybody else happy. My family and friends were really proud and impressed by this fancy office and big salary that I had, but it wasn’t rewarding to me. And when I took that pivot into local government for the city of Chicago, it changed my life completely.

You don’t have to change it radically, but you have to do your part when you’re here on Earth.

Amy Elisa Jackson: How did you find yourself having those conversations with your daughter? I think a lot of mothers struggle with saying “Mommy has to go to work,” or “Mommy’s traveling.”

Valerie Jarrett: One of the strategies that I had with Laura was to try to demystify what I was doing when I wasn’t with her. And so I took her to my office all the time, particularly on weekends. If I had business meetings around the city of Chicago, community meetings, I would take her to those. She traveled with me whenever possible, so she was able to close her eyes and imagine where I was. The other thing I always did, no matter where I was or what I was doing, was take her call if she called me because I wanted her to know that no matter what job I had, she was my first priority.

There are a lot of people who are in jobs where you don’t have that flexibility, but sometimes we just don’t ask for it — and if we asked for it, we could have it. When I was earlier in my career, Amy, I was so busy trying to pretend that all there was, was work. Even pregnant, I can remember just trying to pretend nothing was happening below my neck. It was obvious to everybody, but I thought it would diminish the seriousness with which people took me. And I think that’s wrong. We should tell our children about what we’re doing when we’re not with them, and we should bring the rest of our life with us to work. The reason that’s important is number one, people can’t help you meet your demands outside of work unless they know what they are, and number two, it’s how you build relationships. You have to be open and vulnerable, and you have to be a whole person in order for somebody to really care about you — they can’t just see your work product. Yes, it better be excellent, but that, plus them getting to know you, is what really solidifies the bonds of trust so you can be as productive as you can and so that people want to mentor you, advocate for you and invest in you. They’re not going to do that for somebody who just works — there has to be a human dimension as well.

Amy Elisa Jackson: What was the most challenging part of going from local politics to being a CEO, advisor and now boardmember?

Valerie Jarrett: Getting used to change. I come from an administration that believed in hope and change, but nobody said those were easy. I’m not a spontaneous person by nature. I’m a planner. And I think what I had to do was get comfortable with the notion that initially, change was going to feel uncomfortable. I was going to feel imposter syndrome and feel unsure about whether or not I would be able to meet expectations — just those natural insecurities that most people have but don’t talk about. And I had to say, “With your track record, you know now that it’s going to seem really hard on the first day, and then it’s going to get better.” I wish that when I was 30, I would have known that it does get better. Once it sinks in and you develop new skills, you can meet the challenge.

Amy Elisa Jackson: One of the passages in your book that I highlighted is: “I had ambitiously created this plan for my life. I had this notion that by sheer force of will, I could drive my life in a rigid linear path, and that it was a sign of strength if I had the self-control to never waiver from my intended course.” When you hear that now, what comes to mind?

Valerie Jarrett: I took pride in fulfilling what I set out to do. My parents used to say that when you start something, you have to finish it. So if I started taking piano lessons at the beginning of the school year and I didn’t like it, I had to finish it out. It took a while to get comfortable with this notion that there are always going to be zigs and zags. Some of them are intentional, but some of them just come at you, and learning that it’s okay to change course is important. I thought that once you start a job, or even start a marriage, you should will it to work. Sometimes, though, that’s not possible. But just because something doesn’t work out doesn’t define you as a failure. That’s how I felt when I got a divorce initially. I used to say to Laura, “Look, if you have one happy parent, that’s more than most people have.” I knew that if I’d stayed married, she would’ve had two unhappy parents.

Amy Elisa Jackson: A family legacy of educational and professional success can be inspiring and empowering, but it can also conjure up the fear of never living up to it. How did you navigate that?

Valerie Jarrett: My parents and my grandmother were very open about, and proud of, our family history. My grandmother talked about my great grandfather, who was the first African-American to go to MIT. His father had been born a slave, freed after the Civil War and saved enough money as a carpenter to send his son from Wilmington, North Carolina to Boston. I looked at how successful he was and thought, “That’s a steep climb for anybody.” But on the other hand, anytime I would get nervous, I would think about those folks. I would think, “If you could get on a train, go to MIT and be the first African-American student there, then I can do whatever it is I have to do.” It gave me strength and courage. Then my parents were very good about saying, “What’s most important is effort. Effort will lead to excellence.” But excellence doesn’t always mean getting an A+ — it’s defined by whether you did the best you could. Knowing that my parents loved me unconditionally — and that they would catch me if I did stumble and fall — motivated me.

It takes a certain level of confidence to say, “I’m going to try something really different, even if everybody’s telling me it’s a mistake.” Sometimes, we get so caught up that we don’t realize that when something doesn’t work out, you just move onto something new the next day. [Your career is] a marathon, and each leg of that marathon has different challenges, trade-offs, opportunities and setbacks. You often hear, “Can you have it all?” But when you look back, maybe the question should be, “Did I have a whole life? Did I love, and did people love me? Was I purposeful? Do I feel as though I have the respect of those who I love and cherish? And did I do something to make the world a little bit better?” You don’t have to change it radically, but you have to do your part when you’re here on Earth.

I’ve learned not to plan too far out in the future.

Amy Elisa Jackson: What has been the most impactful thing you’ve learned in the last 10-15 years?

Valerie Jarrett: One of the many lessons I learned in the White House is that you cannot get thrown off course because if you do, you’re wasting time. There were times when I would come in flustered and President Obama would say, “Have you been looking at cable TV?” It was kind of a subtle reminder to take the long view, and to look beyond that 24-hour cycle and say, “Where are we really trying to move our agenda forward?” Yes, we have to react if there’s an oil spill or a hurricane, or even mistakes like when the Healthcare.gov site crashed, but you can’t let that distract you from moving forward with your agenda. Learning that balance is a skill I had to hone. And in doing so, you have to learn to absorb pain, because there were a lot of people who aren’t going to be with you taking that long view. You’re asking them to change, and people don’t like to change. The Affordable Care Act was unpopular for so long, and now the only reason it’s the law of the land is that everybody rose up and said, “Wait a minute, don’t take my healthcare away from me.” But it took a while, and we could have easily said, “We’re burning through political capital — maybe we shouldn’t do it.” President Obama’s attitude was, “What’s the point of having political capital unless you’re willing to use it to be a force for good?” That level of selflessness is what belongs in public service. It’s not about you — it’s about service. But that does take an inner core of strength and resilience that I’m still working on.

Amy Elisa Jackson: In your book, you talk about having a clear and firm voice — this unwavering calm. How did you harness your authentic voice while being in the political spotlight?

Valerie Jarrett: When President Obama took office, we were in a horrible economic crisis. Banks were on the verge of collapse, the automobile industry was in bankruptcy and we had two wars — we had a lot on our plate. There weren’t always good options or great options on the table, and we had to figure out how to make informed, thoughtful decisions quickly, then move on to the next decision. You can’t be myopic when you have 10 things going wrong — it’s like playing whack-a-mole every single day.

People often say to me, “How on Earth did you last for eight years in the administration?” First of all, it never in my wildest dreams occurred to me to leave. I went in knowing that this was going to be the best job I’d ever have. I was working for a president who I don’t just respect but love like a brother. There’s a lot of pressure and you’re working 24/7. I would wake up every single morning terrified about what was going to happen that day — would we be able to rise to the occasion? But after the first term when he was reelected, it was so affirmational.

Amy Elisa Jackson: How would you describe your voice today, in this new chapter of your life?

Valerie Jarrett: Today, I have a portfolio of things that I’m doing. When I left the administration, I did some soul searching. And I thought, “Now that you don’t have a job, you can wake up in the morning and do whatever you want to do. What is it that you really care about?” I thought, “Well, I care a lot about gender equity,” so I started an organization called the United State of Women together with Tina Tchen as an outgrowth of the work we did at the White House Council on Women and Girls. I care a great deal about civic engagement as well, so I’m helping President Obama with the Obama Foundation, which aims to teach the next generation the best practices in civic engagement. And then Mrs. Obama and I started an organization called When We All Vote, a nonpartisan project designed to change the culture around voting in our country. I joined the faculty at the University of Chicago Law School where there’s just a treasure trove of both smart faculty and students that are helping in areas like criminal justice, which I also care a great deal about. I joined the boards of companies where I share values with the CEOs, and their mission is one that resonates with me and is making the world a better place. I’ve been very, very rigorous in my selection process because time is the most important thing I have in this chapter. And I am going to really love being a grandma.

Amy Elisa Jackson: Lastly, Valerie, as we look ahead to 2020, what are you in pursuit of?

Valerie Jarrett: As I said, I’ve learned not to plan too far out in the future. That 10-year plan didn’t go so well for me — I’m really doing it quarter by quarter. So I know what I want to do between now and the end of the year, which is to help my daughter and son-in-law with his transition into a new family that they have created and be as available to them as possible. I’m also working on the paperback version of my book, which I need to get wrapped up by November. And I want to get back to the University of Chicago and spend some time with the students and my mom.

Originally published on Glassdoor.

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