written by Stacey Lindsay

Take one look at the career of Deesha Dyer—which includes social secretary for the Obama White House, founder and CEO of a social impact firm, sought-after strategist, and author—and you'd be forgiven for thinking: She had it all paved out in front of her. 

The truth is anything but. Deesha's journey is one of significant grit, gumption, and bold dreams. In 2009, then a 31-year-old community college student, Deesha applied for an internship at The White House, a role she saw as a moonshot. She got it—and she spent the next eight-plus years of her life working under President and Mrs. Obama, arranging the official and personal events hosted at the White House, where leaders from Singapore to Italy and icons from Beyonce to Aretha Franklin attended. 

Deesha was killing it in one of the most coveted jobs in the nation, but she still wrestled with imposter syndrome and a feeling of inferiority. She writes about all this with wit and honesty in her new Undiplomatic: How My Attitude Created the Best Kind of Trouble. As the 46-year-old CEO of the social impact firm Hook and Fasten tells us, she's proud of all she accomplished, and she has found a way to step beyond self-doubt, but she wants every woman to know it's still a journey—and we're all in this together.

"Sometimes just knowing that you're not the only one is what you need," says Deesha.

Chatting with Deesha Dyer

Deesha, you're honest about your doubts around applying to The White House and all the things you felt were against you. You write, "I had an eviction on my record and terrible credit, I'd written about a past abortion in a newspaper, and I didn't have any connections to politics." Considering everything you've worked through, what does that line bring up now?

When you're doing things and going through life, you're not thinking, Oh, I'm doing this so I can write a book in 10 years. Or, I will get to see the other side of this. What we see is the right now, and sometimes the right now can be really hard. So what that line says to me right now is it gives me motivation to keep going. We don't always know the testimony that we're brewing or that we're going to tell in the future. Sometimes, we don't even know if we'll survive as women. Now, I look back on those times and think, Whatever you're going through, now you're going to make it through. I try to look at things from that angle. 

It took me seven years to write this book. Partially because it took me a while to reconcile that I spent my entire thirties at the White House. I learned to be kinder to myself. The hard thing about writing the book was that I had to write about my past self. I was so mean to myself. I was down on myself and didn't want to lie about that in the book. I was very honest about the negative self-talk. But I move forward with compassion for myself now; hopefully, most of us can do that. 

You have talked and written honestly about impostor syndrome, which many of us deal with. What's important that you want other women to know?

Impostor syndrome, as I call it now, is an oppressive term of illusion. What happens as women, and especially as a black woman and other historically oppressed groups, is we've been fed these images and messages throughout our time. I'm 46, and when I was growing up, it wasn't a time of girl power or speaking your mind. So we've been fed all these messages, and they dig root in us. Then, the next thing we know, we're growing up as imposter syndrome is growing. We hear messages through elementary, middle, high school, and college, and we go get a job; we look at the statistics of how much women are paid and no family leaves. Of course, we're going to internalize all that. We'll think, do we really matter? And what happens is that we turn that on ourselves. Like we turn it on ourselves to think, This is my fault. I don't have as much education as I should. I wasn't as bossy as I should have been. Or I was too this or too that. 

But now I say, no, no. Don't do that to yourself. You are qualified just as you are. You are worthy, you are deserving, and the standards of success we were never meant to reach will always be out of your way, according to someone else. Once I cut the puppet strings of knowing that it was not my fault and I dug up the root, I was like, Never again. It doesn't mean it doesn't come back. But I say now that imposter syndrome can no longer build a home in me. A part of me had to mourn that I spent all that time thinking I wasn't good enough. I can't ever get those years back. So now, I've got to forgive myself for that.

Politics never interested you until Barack Hussein Obama declared his candidacy—and won. Like so many of us, you were dancing on the streets that day. What did watching President Obama campaign and win teach you about dreaming big?

I am still that person on November 4, 2008, on the streets dancing, when it was pouring down rain, and all these adults were bringing up their old instruments from high school and playing trombone. It was like a crazy party. For me, that magic of that night, that dream, I held on to for eight years, and I never let go of it. I never let myself get cynical, no matter how hard it was. I still feel like that person in the rain in November 2008. My career was so far-fetched to me at one time, and then I saw a pathway to make that happen. But there was no way I was going to be suited up and booted up like a [Washington] DC person. No way. My mouth was almost open for eight years. And no matter how hard it got, I always though, I get to do this. It's still like a fairy tale to me, working for President and Mrs. Obama.

The book is out and it's in people's hands. How has it felt to have people read your story so intimately?

I will tell you that I am completely floored. I'm not a Roxane Gay or Zadie Smith. I just write the way I talk. I did not realize how many people would appreciate the simplicity and the mistakes because life is messy. The reception I've gotten back has been mainly: 'You're so real, yourself, and authentic.' And I can tell you, that's not what I expected. It's a book about my life, but I'm not a celebrity. People have reacted to it in such a way that you know, it makes me feel really good about what I wrote. The biggest compliment is that people say that they feel seen. When writing my book, I knew I didn't want to be prescriptive; I just wanted people to know that they're not alone, and that they’re seen and we're on this journey together. And sometimes, just knowing that you're not the only one is exactly what you need. 

I wanted to be very clear in my book that, yes, I accomplished these great things, and it was so wonderful, but that impostor syndrome came with me. I wanted to be real. That was so important for me. 

You formed your company, Hook and Fasten, in 2020. Tell us about that journey and its roots.

I did a Harvard Residency Fellowship and called Impostor to Impact for the students from September to December 2019. Then, I planned to go overseas and live somewhere and get a great job—then the pandemic hit, and I had to figure out what I would do. I started advising companies how to authentically help communities hurting because of COVID— the Bronx, Detroit, Philadelphia. Then, the murder of George Floyd happened, and the company itself transformed into a place where partner corporations and communities can come together in real partnership. I am the bridge between the two, the corporations and the communities, always making sure that the partnership is authentic and equal. What we're doing is sustainable in giving resources and funds to communities, but that doesn't mean we control them. We ask the communities what they need. So now, because the corporations trust me, and I'm trusted by the communities that form Hook and Fasten. I'm working with an infant formula company where we spearheaded an initiative that gives formula to babies at or below the poverty line. We work with the local organizations on the ground. I've never owned a business, so it's been a journey, but I'm very thankful for it. 

But I have to say, I still want to live overseas one day! 

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Deesha Dyer is an award-winning event strategist, community leader, author, speaker, founder & CEO. Learn more at deeshadyer.com.

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