The Obamas’ former social secretary has advice for Philly girls

It wasn’t her time as the Obamas’ social secretary that inspired Deesha Dyer to pen Undiplomatic: How My Attitude Created the Best Kind of Trouble.

It was the 46-year-old’s commitment to boosting young women’s self-esteem that inspired Dyer, founder of begirl. World Global Scholars, a nonprofit that encourages Philadelphia girls to travel, that motivated her to tell her life story.

“I work with young girls and they tell me all of the time: ‘I’m not worthy. I’m not valued. I’m not deserving. I’m dumb. I’m ugly,’” Dyer told me in a video interview. “[Young women] have always dealt with these feelings. This book is my way of sounding the alarm about it.”

Everything about Undiplomatic is Philly. Its cover features the city’s skyline and the bottom half of her face — complete with nose ring and sparkling hoops — hovering over it like a full moon. When we meet Dyer in the book, it’s 1987 and she’s 9-years-old, with divorced parents, starting boarding school at Milton Hershey School. There she would be branded a troublemaker, a reputation that would haunt her feelings of self-worth for decades. She later enrolled at the University of Cincinnati and dropped out due to poor grades.

Dyer moved back to Philadelphia and landed a gig at a Center City real estate company. She wrote freelance articles about the Philly hip-hop scene for local newspapers and websites and on the weekend, danced the nights away at Five Spot, Zanzibar Blue, and Fluid. In 2009, she applied to be a White House intern while working and taking classes at Community College of Philadelphia. When she was offered the internship, her life changed. But her bout with imposter syndrome was just beginning.

“Washington is very crème de la crème, very buttoned up. Very zipped up,” Dyer said. “I didn’t follow the diplomacy, the protocol.”

As the Obamas’ social secretary Dyer brought The Roots, DJ Jazzy Jeff, Jill Scott, and Kendrick Lamar to the White House. She hosted Pope Francis’ 2015 Capital City visit and coordinated state dinners. Still, Dyer didn’t feel like she belonged, sacrificing her health and well-being to prove her worthiness. It wasn’t until she left the White House that she was able to reflect. “My rise was unconventional,” she said. “But it’s [also] what got me promoted to a top White House job.”

Today Dyer is married, owns Washington-based corporate consulting firm Hook & Fasten, and regularly talks to young girls all over the country about how to deal with imposter syndrome. She offers this advice to young girls — and women — struggling to feel like they belong.

“I don’t give girls advice on how to thrive in the workplace,” Dyer said. “I give them advice about how to thrive as a whole person.” To Dyer this means keeping up with doctors’ appointments and seeing a therapist. The answer isn’t always to do more, but sitting a spell. “I don’t come at young women with the mindset that being successful in anything — especially the White House — is to do more, more internships, more jobs. Sometimes it’s about doing less and honoring your capacity.”

“People are always telling women to be professional,” Dyer said. “They expect 18-, 19-, 26-year-old women to behave like they are 46, like they have it under control. Well, that’s not realistic.” We can’t ask young women to ignore who they are now to accommodate who they may become later, Dyer said. So, “if these women want to wear cropped tops, I’m OK with it. If her hair is shaved or in an Afro or a lace front [wig], that’s fine too. We say we are an open society, but way too often we judge. I want girls to be who they want to be, that’s the only way they can figure out who they can be.”

“[Young girls should] meet themselves where they are,” Dyer said. “If they don’t want to go to college — and I know Mrs. Obama would kill me for saying this — then perhaps they shouldn’t go right now.” Dyer tells teens to figure out what they want to do. “Maybe it’s going to community college, maybe it’s doing a gap year. Listen to the voice in your head.”

Imposter syndrome is a form of oppression, Dyer said. The bottom line is that it’s not real. And there is always something from our past that’s triggering why we feel that other people’s credentials and life experiences overshadow our own. “You have to get at the root,” Dyer said. “Sometimes it’s from social media, sometimes it’s because you didn’t get something you wanted. Sometimes it’s from gaining or losing weight. What is that made you not feel worthy?” Dyer asked. Once you determine that, then it’s about overcoming it through therapy, faith, and being aware. “Imposter syndrome may never go away, but it shouldn’t define who you are.”

Deesha Dyer will read from and sign copies of “Undiplomatic: How My Attitude Created the Best Kind of Trouble” at Barnes & Noble, 1708 Chestnut St., on Tuesday, April 30, at 6 p.m. Dyer will be joined in conversation by Errin Haines, editor-at-large for The 19th. Space is limited. Register through eventbrite.