Tiffany Dufu Wants You to Cut Yourself Some Slack

May 19, 2017 | Filed in: Woman of the Week

When you ask Tiffany Dufu about her job, her answer sounds more like a mantra: “My work is to advance women and girls,” she says. Indeed, her resume reads like a one-woman crusader’s checklist: She helped launch an all-girls middle school, served as the president of the White House Project (a non-profit that worked to increase female representation in businesses, institutions, and government), and is currently the chief leadership officer at Levo League, a company that helps millennials plot meaningful careers. Last spring, she published her first book, Drop the Ball: Achieving More by Doing Less, a memoir-slash-manifesto about how women can create higher-functioning lives by giving themselves a break (Gloria Steinem wrote the foreword). A few weeks ago, we visited Tiffany at her apartment in Harlem to talk about mentorship, moms, and why finding your purpose might be easier than you think.

I’VE ALWAYS BEEN SURROUNDED by women. When I was little, I spent a lot of time getting my hair done, which takes a good six hours—my mom would even blow-dry it after she took the cornrows out. During this time, she also did her work as a preacher’s wife—there were always women in our home, bringing cakes, talking about things happening in the church. They would gossip, and I would listen to their stories and soak up their energy and wisdom. Being a child in the presence of women who had been there and done that, so to speak, made me want to keep building that ecosystem around me as I grew up. 

ANOTHER REASON I HAD MENTORS at a young age is that when I was 16, I lost touch with my mom. I don’t talk about it a lot in my book, because I wanted to write about experiences I thought would resonate most widely, and I didn’t think this experience would resonate far enough. But during that time in my life, the women at our church really embraced my sister and me. They looked after us and made sure we were taken care of. Now, I seek out that kind of guidance—I crave it, and have a bit of an addiction to it. I think I manage it well, in that I also trust my gut, but my younger sister always says, “Oh my God, Tiffany, you’re so boring. You never want to learn a lesson yourself. You can’t just live your life and make a mistake and learn from that. You always have to get advice from other people.” And it’s very true.

Tiffany wears the Alex 2.0 dress in graphite.

I DO FEEL PRESSURE to make sure that I’m not a burden on my mentors, and I manage that by being a superstar. I do everything I can to ensure that the people who invest in me will get a return on their investment. Every time I get on stage, every time I write another chapter of a book, every time I have a conversation with someone in the media, I’m very cognizant that I’m here because of the people who have supported me, and I want to make them proud. I want to make sure that as I move along in my life and my career, the person who had coffee with me 20 years ago can say, “I know Tiffany, and I’m glad I invested in her because she’s making a difference in the world.” I use those relationships to fuel my impact, because I feel like if I don’t make a difference, I will have wasted those people’s time.

WHEN I GRADUATED from college, I sent an email to two professors that had made a huge impact on me. I said thank you, and let them know what job I was taking and that I would keep them updated every six months. That was about 20 years ago, and since then, I’ve kept adding new people to that email list—now there’s about 400 people on it. That’s a group of people who have gotten an update twice a year for the last 20 years. I call it my “village updates,” and depending on when you joined the village, you’ve seen me get married, have kids (who are now eight and ten), become president of the White House Project, write this book and get a New York Times review. People sometimes ask me how I’ve maintained all these relationships, and that’s how. Even though we now have social media and I’m on those platforms, it’s not the same—getting emails makes people feel closer. These people are on that list because I have a special relationship with them.

SOMEONE YOU’VE KNOWN a long time can give you clarity and guidance in a way that people you just met can’t. They can say, “Tiffany, we’ve been there before. This is the same issue you’ve already had. When will you learn?” Once, I was in angst about a job opportunity that was in another city, and didn’t want to transplant my family. A mentor said, “Tiffany, I’ve noticed that you’re consistently worried about decisions you don’t have to make. You have all this anxiety over moving to a new city, and you haven’t even applied for the job! If you spent more energy on generating options for yourself, as opposed to agonizing over decisions you don’t even have to make, you would be much more successful.” A person has to know you to be able to recognize a pattern and help you shift your behavior for your own good.

Tiffany wears the Pauline dress in true olive.

I GREW UP THINKING I’D BE AN EDUCATOR. I was going to be a teacher, and when I got to college, someone suggested I become an English professor. At the end of my Master’s program, I was planning to go straight into my Ph.D. program. One day, I was having lunch with one of my favorite mentors and she asked me, “Why are you going to be an English professor?” And I just kind of sat there. I couldn’t even remember when I had decided that. The only thing I could say was, “When I was a little girl I wrote a lot, and I got good grades on my English papers.” And I thought, What a lame answer! My mentor picked up on it, too. She looked at me and she said, “You do realize that the world is your oyster, right? You can do anything!” I was so struck by that, because it’s something you would tell a ten year old girl, not a young adult who knows where they’re going. It sent me into a career amygdala hijack, and I went to this career development program that was based on the book What Color Is Your Parachute? It was the first time I opened my mind and my horizons to what I could be. It led me to my purpose—which is to advance women and girls through the nonprofit sector. I left my Master’s program, decided I wasn’t going to do my Ph.D. program, and got a job at a foundation.

WE HAVE THIS MYTH about purpose, that it’s something majestic: You’re walking down the street and the skies open up and you drop to your knees and the voice of God says, “You’re here to serve orca whales.” I don’t think it’s that complicated or mystical. I think your purpose is simply a commitment inspired by experience. It’s a decision. I believe it can be engineered. I spend quite a bit of time with women helping them align their story and figure out their purpose based on their experiences.

Tiffany wears the Aditi 2.0 dress in persimmon.

SOMETHING THAT SHAPED my purpose is that my mom got pregnant with me when she was 19. She gave me a very different upbringing from the one she had: Every day she told me I was smart, beautiful, and loved. But when my parents divorced, I discovered overnight that all of the social, political, and economic capital that I thought was our family was really only our dad. He was the breadwinner; he was the one who worked outside the home as a preacher, and he was the one who had the awards from the community. It hit me in a very deep, unsettling way, to have my mother be the woman I knew growing up and then, based on the decisions she made and her reliance on men, end up a victim of domestic violence and living in poverty—you can never shake it. I tried to save my mom and I couldn’t. At some point I realized that she didn’t have the mother that I did. Now, I spend every day trying to instill that same agency that she gave me into as many women as I can. And that’s what Drop the Ball is. It’s me whispering in a woman’s ear saying, “You are so smart and beautiful and loved. You are the most powerful agent in your own journey, but in order for you to do that, you have to cut yourself some slack.”

WOMEN ARE SO SOCIALLY CONDITIONED to be caregivers that we often don’t look at the financial impact of our decisions. We’re told that we need to have careers that are passion-driven; otherwise, we have a hard time justifying why we would go to work and not be at home. Think about the strangeness of that: Economics is a primary factor of providing for your family, and why people work. Providing for your family, as any man would tell you, is a tremendous source of pride that women haven’t been conditioned to believe they can have. In fact, we’re told the opposite—that we’re selfish for wanting to make money, as opposed to spending time with our children. That’s a very privileged place to come from. Think about the immigrant woman who had to leave her children in another country in order to come here and provide for them. For her, earning money is an amazing source of pride and an avenue through which she demonstrates love for her children.

Tiffany wears the Alex 2.0 dress in graphite.

I USED TO TRY SOMETHING ON and ask myself, “Can I wear this dress?” Now I ask myself, “Can this dress wear me?” I think personal style starts with how you feel, being clear about who you are and what you represent, and exuding that through whatever you’re wearing. If I decide I want to look good in a dress, I look good in a dress. I spent a lot of time being self-conscious about my body when I was younger. I’m very small-framed, and while we live in a society where that is worshipped, it was not worshipped in the community I grew up in; you were supposed to have meat on your bones. Now, I love to wear clothes that fit my body well, let me move, and lend me credibility. What I love about your clothes is that they don’t take away from me. I feel like myself in your dresses. The designs don’t distract from who I am and what I want to be in the world.