You’re Always Winging It: Lessons on Success and Entrepreneurship as Parents

“We have this fear that if we let our cracks show people will disappear on us, people won’t respect us, people won’t appreciate us.”

Tiffany Dufu is often described as a catalyst-at-large in the world of women’s leadership. With leading roles in the Lean In launch team, at Levo, and now as the author of of Drop the Ball: Achieving More by Doing Less, Tiffany works to educate and empower millennial women. She recently joined Caroline Clarke for a Heleo Conversation on defining success as an ambitious, working mother in today’s social media-heavy world. Caroline is an award-winning journalist, senior editor at Black Enterprise magazine, author of Postcards from Cookie, and host of Women of Power.

This conversation has been edited and condensed. To view the full conversation, click the video below.

Tiffany: One of the questions that I have is around sustainability and the leadership lessons that you’ve learned. Can you talk about what it means to stay the course, and what it means to be successful at a brand for so long?

Caroline: So much has changed since I went to Black Enterprise. The media has changed, I’ve changed, the company has changed—grown, shrunk, and gone through all sorts of iterations.

Sustainability, it’s an interesting thing. It’s a very personal thing. I’m always fascinated when I interview others who have been at companies their entire careers—Ursula Burns, at Xerox, is one. She’s about to transition, but she’s a lifer at Xerox, and she managed to rise from intern all the way to CEO. That’s mind boggling to me. That was never my goal, never my intention. I had no designs on running the company, on building a brand, on being anywhere for this long. I think, at any time, no matter what business is doing, it’s about checking in with yourself, knowing who you are, knowing what you need to feel successful, and to be satisfied with what you’re doing.

What’s worked for me at Black Enterprise is that the company has gone through such dynamic shifts over the time that I’ve been there. We went from being purely a magazine publishing company with one magazine, to diversifying so that we included television shows, one of which I hosted. I launched a book division at one time, and we’ve had radio, and now a very strong events business that’s anchored by the Women of Power summit. As the company changed and I was able to step in to do things that were entirely new, that I never foresaw, my career changed.

I was always challenged, always exhilarated, always looking to the next thing and feeling critical to the health of the company. Which made me feel needed and validated, and as if what I was doing was really important, not just to the company, but to those we serve. The satisfaction meter was always super high, and that’s what it’s about. When that starts to dip you have to pay attention. That may mean it’s time to shift within a company, that may mean your job itself is not fulfilling, or that may mean it’s just time to go. You’ve got to know you.

Tiffany: Very early in your life and career, you knew that journalism was who you are, that that’s what you wanted to do. You have a daughter who’s twenty-two: what kind of advice do you give to her about making a decision about what you can do?

Caroline: I didn’t always know I wanted to be a journalist. I loved to write, and when I was in college, I decided to major in English, and my chemistry professor father said, “That’s nice, but what are you going to do to earn a living?” He thought the only thing you could do with an English degree was teach. There was no way I was going to teach. I really put those pieces together, like, “How do I write, and get a paycheck every two weeks?” Journalism was the answer. It was not that I had some deep-seated passion. It became that in graduate school. For this generation of kids, they have so much more information than I had. In a sense, they have so many more opportunities, but they’re more splintered, and a lot of them are more ephemeral. All of them require a more entrepreneurial mindset.

“Social media has a place, social media can be great, but you have to manage it and not let it manage you.”

I work at a brand where we interview business people all the time, and entrepreneurs in particular. Not everybody can run a business, not everybody is entrepreneurial. You can train yourself to be that, you certainly have to in this environment, but it just doesn’t come as naturally to some of us. Entrepreneurs have a chip, and it enables them to create something out of nothing, and have a level of persistence and confidence and dedication that is not second nature to most of us. My daughter is that kid. She’s not the most confident in herself, because she doesn’t clearly understand yet exactly what she wants to do, and she has a sense, because of social media, that all of her peers do. Which of course they don’t.

What I tell my daughter, and all of my mentees who hover around that age range, is don’t be fooled by social media. Don’t get drawn into that world in such a way that it drags you to a place that makes you feel less than, because that’s the real risk. It’s this constancy of comparing ourselves to each other, even on this mystical plain where people don’t know you’re looking, and people don’t know you’re measuring yourself against them, but you are. Sometimes you don’t know that you are, and it can work this very insidious thing on you that suppresses who you really are, and what you really bring, and how you really feel about yourself and your future. It’s like, “Oh, I’m not that,” and, “Oh, she’s doing that.” Enough of that. Social media has a place, social media can be great, but you have to manage it and not let it manage you.

Tiffany: That’s right, because you end up with this pressure to meet unrealistic expectations about who you’re supposed to be.

Caroline: None of us are that. None of us are our Facebook self.

Tiffany: You shared this moment about your daughter being in kindergarten, and her going to a book signing the first time that, you might say, she was in awe of you and who you are, because she saw you in a different way. Often our expectations about who we’re supposed to be are very much intertwined and entangled in the relationships we have with our mothers. How do you think that your success has played a role in how she feels about who she is in the world?

Caroline: It’s interesting. So many of us now have somewhat of a public face. We get opportunities to speak, to do videos. That’s not something that we saw our mothers do. When my first book came out we had this book signing, there were maybe one hundred and fifty, two hundred people there, and I spoke. I looked out into the audience, and my daughter’s five-year-old face just took my breath away. I still see that little face, especially on those days where my stuff is a wreck. I’m like, “Oh no, you want that person that she thought was so great.” She had never seen me in that realm, I was just mom.

I think it changed something for her, when she saw me as larger-than-life and very different from mom who was in her sweats dusting, cooking, and scrambling to get cupcakes made for some birthday or bake sale. You wrote your epiphany about the bake sale, “Let it go.” All those things that you’re scrambling to do. Motherhood is the ultimate in winging it.

At Black Enterprise, when they asked me what I wanted to call my blog, I was instantly like, “Winging It,” because that’s all I’m ever doing. How much preparation do we get for most things? A lot of it you’re like, “Lord, please, just don’t let this whole thing fall apart.” Most of the time it doesn’t, but parenthood is the ultimate in winging it. You jump out there, you have a baby, you have only the resources that you were given being parented. It is really tough. I needed my daughter, and I need my son, too, to understand that that is what most of us are doing.

“That is what drives me as a journalist. Yes, I love to write, but why I came to love journalism is I need to know. I’m not that girl who can live with question marks.”

You’re not always going to know what the ground rules are. You’re not always going to know even what the expectation is. You’re not always going to be sure that you have what it takes. You don’t get to back down, because if you don’t try, you’ll never know. That is what drives me as a journalist. Yes, I love to write, but why I came to love journalism is I need to know. I’m not that girl who can live with question marks. It might be the worst answer in the world, I’d rather have the answer than the question mark. That’s why you keep trying, why you keep risking, why you keep putting yourself out there, because you want to know, “What am I capable of? Can I pull it off?”

Sometimes you can’t, but maybe it was just that day. Maybe the next week you nail it. So you keep coming back, and that’s what I want my daughter to know, what every mother who’s lived long enough knows, that you wish you knew when you were starting: if you just keep showing up, in the most basic way, not picture perfect, you can get there. It’s not going to be a straight line, may not be everything you expected. I’ve done a lot of jobs I didn’t expect to do, even within one company. But you’ll have those moments where you’re like, “Wow, I got this.”

Tiffany: It turns out that your questioning and your curiosity are in part what led to a very personal and important discovery that has shaped who you are. Can you share a little bit?

Caroline: I was adopted at the age of a month. I didn’t know anything about my birth parents other than that they had been very young and they couldn’t keep me. My mother told me a very beautiful story about how all of my deceased grandparents were in heaven and had chosen me out from all the little baby spirits that were waiting to come down to Earth because I was meant to be their child, and they had sent me just to them.

I believed that story. It is corny as all get out, but I love that story, and I still believe that. I was really content. I had the most wonderful parents, I believed I was where I was destined to be, but I knew that I could get medical information, and once I had my own children I wanted that. I went in search of it. I was presented with what’s called a social history, which did contain some medical information, and also extraneous facts about my biological family. I realized, in hearing these facts, the number of children in the family, birth order, that I knew this family. It turned out my birth mother was the oldest sister of a dear friend of mine.

It’s amazing, but I wrote the story because I feel that my story demonstrates if you really lean into life and trust it, trust that it’s going to hold you up, it’s not going to let you fall, it’ll do just that. It circles back around in the most amazing ways. I hope that the book will uplift and reassure people of that, because I think it’s a fundamental truth. We’re not here to fail. We’re here to flourish. If you believe in it, and yourself, you’ll see it all happen all the time.

“We have this fear that if we let our cracks show people will disappear on us, people won’t respect us, people won’t appreciate us. It’s not enough to just run every day, you have to run a marathon. It’s not enough to bake a cake, you’ve got to make this unbelievable creation. It is enough. You are enough.”

Tiffany: Absolutely. Do you have any parting wisdom that your mothers, looking down, you feel like they would give to us today?

Caroline: We’re all constantly trying so hard to be unflappable. We use the word “perfection” all the time. But we’re human. It wasn’t my mother, it was my father who said every single day, “Nobody’s perfect.” We have this fear that if we let our cracks show people will disappear on us, people won’t respect us, people won’t appreciate us. It’s not enough to just run every day, you have to run a marathon. It’s not enough to bake a cake, you’ve got to make this unbelievable creation. It is enough. You are enough.

What I tell my children is what my parents told me. “You are enough. God created you, only you can bring to the world what he intended you to bring to the world. Bring that, whatever it is.” It’s not about what the other person’s doing, it’s not about what your boss wants from you. It’s about what the universe wants from you, needs from you, intends to get from you that only you can give. That is not about perfection. It’s about being in touch with who you are and what you want to give to the world. You’ve got to give it something, or what’s the point? But it’ll be enough. Whatever it is for you, it’s what we need from you, and it’ll be enough.