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“You Don’t Know How Many People Are In Your Corner Until You Remove Yourself Out Of Your Own Way” – Deesha Dyer On Taking Risks and Tackling Imposter Syndrome

by Brendan Dowling on April 26, 2024

In her candid and vulnerable memoir, Undiplomatic, Deesha Dyer shares stories from her extraordinary life, whether it’s flying on Air Force One or a memorable job interview with Michelle Obama. Dyer was a thirty-one-year-old community college student in Philadelphia when she applied for an internship at the White House. Dyer knew she was an unconventional candidate, but she quickly proved herself to be an invaluable member of the team in the Office of Scheduling and Advance. Following her internship, Dyer was hired to work full time in the same office. She earned a series of promotions, and was ultimately appointed to serve as the White House Social Secretary for the final two years of the Obama administration. In that role, Deesha oversaw all official and personal social events given by President Obama and his family. Her tenure included what observers at the time called a “diplomatic trifecta”: a visit from Pope Francis, a state visit by President Xi Jinping of China, and the President’s reception for the UN General Assembly, all taking place within the span of a week. Dyer has remained similarly active since her time at the White House, serving as a Resident Fellow for the Harvard Kennedy School Institute of Politics and founding Hook and Fasten, a social impact firm. More than a political memoir, Undiplomatic serves as a clarion call to eradicate imposter syndrome, as Dyer vulnerably shares her lifelong struggle with self-doubt, how it haunted her at various points in her career, and the step she took to confront it. Author photo courtesy of Ellen Shope-Whitley.

I wanted to start by talking about the role of music in your life. It starts with you listening to Jill Scott and music plays a huge part throughout the book. Can you talk about your relationship with music?

My parents always listened to music—just like every other Black family, cleaning the house and listening to Anita Baker, Patti LaBelle and Sadé. My love of music really comes from my parents. As you’ve read the book, you know I love theme songs of shows. I just always thought they were so catchy and fun. 

When I got older, I was always very much into the lyrics. I’d be the person that would record a song on the radio and then keep playing it to write the lyrics out for no reason. I just found an escape in music. Like in my Fiona Apple time, if I was going through a breakup, I’d be like, “Yeah! She’s speaking for me!” (laughs)

I’ve always been into hip hop, but I think that my love of hip hop really started and was cultivated when I discovered breakdancing and graffiti. I got deeper into it once I realized that women were not recognized as pioneers in the game.  They were all underground or behind the mic, and I was like, “No, we need to figure out a way to highlight them.”

Is that what prompted you to work as a music journalist when you were in your twenties?

It definitely is. Every element of hip hop—from breakdancing to beatboxing to being a DJ to being an MC to being a graffiti artist—I was not talented enough to do any of those things professionally or even as an artist. But I didn’t see that as a bad thing, because it was like, “I’m a fan,” you know? And I think that there’s a space for fans. But what I did know how to do was write. I just reached out to a friend and was like, “I’d love to start writing more about the culture—the women in the culture, the underground culture.”  And it was when everybody was coming out with their little websites with forums in the day. So that’s what started it, being able to take two things I love—writing and hip hop—and combining them.

The reader goes on such a journey with you. We start with you as a community college student finding out you got an internship at the White House and end where you are now, running your own company. Can you talk about how you chose to structure your memoir?

I had to remember that a memoir is not your whole life. I’m educated in a lot of things, but I’m very clear when I need to say, “I don’t know how to do this.” I’ll admit that I don’t know! (laughs) It was very scary writing a memoir, because I had to pick a certain time in my life. But that’s so revealing. I had this really cool job and I went through this really excruciating impostor syndrome thing. I wanted to grab the reader in the beginning by describing what my internship and that process looked like. As soon as I did that, I was like, “Okay, now I want to take people back to the time where I first started feeling like I wasn’t worthy,” which was as a child. I wanted to set that up so people saw the different worlds. I didn’t want it to just be, “Okay, she had this thing at the White House, great. Now, let’s go through her whole career.”  I’d be doing myself and everyone else a disservice if I decided to say, “I have impostor syndrome and I had this job. I didn’t know where [the imposter syndrome] came from.” No, I knew where it came from.

I tried to structure it in a way so people saw the evolution of me through the book, so they didn’t get to the glory days of like, “I went to therapy and am now doing better, blah blah blah.” I didn’t want to skip the hard parts. I tried to put [the hard parts] throughout, and it was very important for me to put it there in the beginning.

As a reader, I definitely had the sense of watching someone learn and grow throughout the course of not only a lifetime but also the eight or so years that you focus on at the White House. What went into deciding what stories to include and what stories to leave out?

I think a lot of deciding was my own fear of how people would receive some of the things that ultimately could have been in there. I think although it’s my own truth—and I was walking my truth, I believe in my truth—I’m still not inconsiderate of people’s feelings. Even if they did me wrong, it does no good for me to put out this energy of “this person effed me over.” It doesn’t solve anything. That’s not what I’m trying to do, right? I decided to leave out those stories, but I also decided to leave out a lot of the more traumatic or triggering things. I believe that if you lived through something you’re allowed to talk about it. I don’t feel like we should be policing when people need to talk about their trauma or not. If you don’t want to read it, don’t read it. But for me, this memoir is focused on my White House time and so that’s what I wanted to highlight. I knew that people wanted to hear the fun stories and I knew they wanted to hear the insider stuff. I tried to put stuff in there that would catch the reader’s eye, make them laugh, or go behind the scenes. Something like, “she lives in this world,” but also for [readers] to say, “Wow, she was on top of the world with these amazing, fun stories, but she still felt this way.” I wanted to humanize it a little bit because if I just stuck to White House stories all the time, come on! “Oh, wow, this privileged person! Look at her writing a book about parties!” No, I wanted to be humanized, because I feel like if I share real experiences and real stories from my life then people can relate to me more. They can maybe see themselves finding more confidence in themselves and reverse this imposter syndrome that so many people feel.

One of the really poignant parts of your book is when you write about an experience you had while working at an Au Bon Pain as a teenager. For me, I was able to draw parallels to your experience as a high school student to similar experiences you would have had in later work environments.

Exactly. I think that that’s the thing. I also wanted to make sure people knew that I didn’t walk out the womb to the White House. I worked at a mall, you know what I mean? I say that because I wanted to show the different levels that exist when it comes to Black women in the workplace, or somebody who’s more bold or somebody that speaks a lot. I wanted to show that it’s on all levels. When I worked there, we didn’t have social media, so we didn’t know anybody else was going through this.

I want to get back to talking about applying for the White House internship, because that chapter specifically is so crucial to the book. You write, “I wasn’t what I would call the ideal candidate, but I was the right one.” Can you talk about what you meant by that?

I feel like I was not the person who, if you were putting [together a list of] who wants a White House Internship, like no one was coming to find Deesha Dyer in West Philadelphia, you know? Nobody was looking for this lack-of-formal-education-kind of person who had been evicted and had no money. That wasn’t ideal, right? But I say I was the right one because those qualities absolutely made me the right candidate for it. I had this community background. I was thirty-one when applying for the internship. I feel like I was right for that job. There was a mystique that surrounds White House internships and it’s just like, “Let’s get our ideal candidate because that’s what people want.” It’s the normalcy of it all. And that’s the Harvard grad or so-and-so’s daughter. No, actually, that’s your ideal candidate, but that’s not the right one, because you perhaps need somebody who’s had some life experience or somebody who has a different take on the political world. We had a Black President for the first time and a Black First Lady. So maybe you don’t need the ideal person. Maybe you need a person who will look at it and say, “This is new, this is something different, and I want to approach this in a different way because we’re actually dealing with a different President, a different First Lady and a different agenda.”

When you explore your time after the internship and you’re back in Philly, you write, “It was safer to stay in a box I knew instead of constructing one with an unknown outcome from scratch.” It seems that so much of this book is how you learned to become comfortable with taking the leap into unknown outcomes. What shifted in to allow you to begin doing that?

Honestly, I think some of it was age and maturity. At that point I had a list of things I had accomplished, really big things and really hard things. I was just like, “I have a roster of evidence that when I take a chance, it works or it doesn’t. And if it doesn’t work, I don’t die.”  It’s hard—I’m not going to minimize that when you get disappointed, it’s hard. But it was fine!  Life kept going after I had mourned it or grieved it. When people ask me, “How did you get there?,” I almost felt like I had no choice. I didn’t grow up with a lot of money. I had to work or I would have been homeless, you know what I mean? There was no fallback plan ever. So I was like, “Well, why not take a risk? What’s going to happen? Great, I’m not going to get the internship and still be going to school and doing what I’m doing.” It wasn’t a bad thing. I feel like I take risks because that’s one thing I’m not afraid of, because I’m just like, “Why not? What’s the consequence of me not doing this?” The consequence is I’m in the same place I was, which most of the time is not a bad place. It’s not. Once I took the risk, applied for the internship, and got it, I also became really addicted to like, “What else can I do?” I was like a mad scientist. (laughs) I was like, “Oh my God, what else can I do? Oh my God, I can get promoted. Oh my God, I can travel the world. I can go to Harvard.” It became an addiction of like, “This is kind of fun!” So that’s how I looked at it. And you know, I’ve slowed down a little bit in the risk factor, but I still do that even today.

That carries throughout the book. Without spoiling anything, towards the end you share an experience of being disappointed by something that didn’t work out. That’s such a powerful moment, because even after all your amazing accomplishments we see there are still disappointments. You seem to be saying, “There are still setbacks, and I’m still going through them.”

Yeah, definitely. I wanted to be honest and real about that because there is—again, I use the word mystique a lot—but there is a mystique of like, “Oh, I worked at the White House and I was a fellow at Harvard and I did all this stuff so the world is at my hands. Like duh, who wouldn’t hire me? Who wouldn’t want to have you as a fellow? Who wouldn’t want to give you all these opportunities?” I wanted to be honest about that because it isn’t our accomplishments that give us confidence, it’s about who we are at the foundation that can’t be shaken. Yes, I tried to build something on that foundation, which was getting a new job, right? I was like, “Okay, I know who I am,” and then it didn’t work. But when it didn’t work the house falls, but the foundation is sturdy. You have to have a foundation of who you are and your worth outside of your accomplishments, because things come and go. Things really come and go. I really wanted to humanize myself because I was like, “These people out here thinking I’m eating caviar for breakfast!” People think the weirdest things about the White House Social Secretary, because it usually is a very crème de la creme role. I’m like, “Yeah, I brought a different crème de la creme to the table.” (laughs)

When you write about taking on the role of the Social Secretary, you talk about how you made the conscious decision that you weren’t going to seek external validation, but really focus on internal validation. Can you talk about the skills that you brought to that role that allowed you to thrive?

I’ll be completely honest, I think that all started off with my community. The role that I had as White House Social Secretary was convening, gatherings, events, and making people feel welcomed. The President and First Lady—the First Lady especially—their thing was opening up the house. “How can we open it up so it can be the people’s house?” Again going back to the foundation, that is someone I was before I even knew who Barack Obama was. I always was an inclusive person. I always had gatherings, whether it was with no money or with a lot of people. I always was like, “Let’s bring people together.” I was always about that life. Once I went to the White House, I think that was a strength of mine that helped me. I think the other part was that we had a Black President and First Lady. I think that having a Black President and First Lady who were cool, who were cultured, who were organizers from Chicago, all of that gave me a confidence to be like, “I can do this job, because I feel like these are people I would have met in my life. I’ve met people like this in my life at other points in time, so this is just like we’re community-building together. We’re problem solving together like we were at a small organization.” I think I had the ability to see them as Barack and Michelle Obama from Chicago, which is how I encountered them when they first came on my television.

I never lost that.  I never lost the wonder of these two people. Even though we’re at the White House, and they were the President and First Lady, and obviously there was the diplomacy and all that stuff, I think in the end because I always saw them these are two people who wanted to change the world—the same feeling I had in 2007, when I heard the first speech right? That ability to see them in that way was such a unique thing for me, because I was able to be like, “Oh, all right, I got this. This is what I used to do. This is who I am.” There was stuff I had to learn of course, right? But I think that was the basis of why I was able to do my job so well.

You write in the book about how you did all this volunteering and community outreach in your twenties with different organizations, but you also continued to do volunteer work during your time at the White House, right? Why was that important to you to still maintain that aspect of your life even when you had this incredibly prestigious position?

You know, it was important for me because that was my family. That was my home. That was when I felt most like myself. That is where I belonged. The White House—I belonged there too, obviously. But I would go to Carpenter’s Shelter and I’d serve dinner and sit around and play checkers or play with the kids. It was a sense of normalcy for me. They didn’t know I worked at the White House, they didn’t know who I was. I was a volunteer coming in. I was also giving back for selfish reasons of making sure that I felt like I never left my community. I felt welcomed and loved and I had a great time and I was able to help serve people. It was important for me to maintain that part of myself, because I wanted to stay in touch with the community. The White House is an amazing place. We definitely welcomed in community, but to go somewhere and meet someone on the level where they are—to go in their house, to go in their home, to go in their shelter, to speak to them like a human being—that’s my gift. It was very important for me to maintain that and to never lose sight of that. And to have fun! I had a great time. You know, I had a great time. I would go volunteer with women who were formerly incarcerated. Just listening to them and hearing them made me better at my job, because it made me never forget why I’m there. I can’t change their life, but I can invite them in for a tour. How amazing is that? That was something I felt like I had to do and I loved that, you know? So that’s why it was important.

A huge part of the book is you writing candidly about your experience with impostor syndrome throughout your life. Can you talk about what imposter syndrome is? Could you share some of the strategies that have worked for you dealing with it?

So imposter syndrome is a term that basically says you feel like a fraud. It makes people feel like they don’t deserve things, that people are going to find out that they’re imposters in the workplace or their professional life. They don’t feel deserving of their promotions or opportunities. They’re always questioning, “Do I deserve this” or “do I belong?” My relationship with impostor syndrome has evolved. In the book, it basically says that now in my present body at forty-six, I’m like, “This is a sham.” It’s a sham, because who told us that we were not qualified? Any messages we got from people saying that or insinuating that or microaggressions/aggressions, those are all systems that play to keep us where we are. It affects mainly those who have been historically oppressed—Black folks, LGBTQ folks, people with disabilities—we’re the ones who suffer the most from impostor syndrome, because this world is not meant for us to be in power, to be equal. I started having this realization, “Wait a minute, this is not my fault or my responsibility, because I know that I’m qualified. I just did eight years at the White House. I got hired and moved up.” Once I realized that, I had to do the deep work of reversing it. I had to get my confidence that I never knew was there. Where do I find it? Because I didn’t know. Now that I’ve moved this weight off my chest—of impostor syndrome being my fault—where do I find the confidence? I think the book really takes you through the evolution of that.

It would have been really easy for me to write the book in the present body in which I am where it’s just like, “I’m healed! Praise the Lord!” Instead I wanted to take you through the evolution, because most people are not where I am. I talk to so many people who come up to me after speaking gigs. They all are in this place of, “I don’t think I deserve it.” It does me no good to give you the ending. Let me let you see how I went through it.

One tip is realizing that it’s a sham and accepting that it was not your fault. Then going back from there and saying to yourself, “Look at all that I accomplished. Look at all that I am. I did this because of who I am. I deserve these things. I curated these opportunities.” People should look at their roster of what they’ve done and what it took to get there to make it happen. But then also going back and digging up the root of when you started feeling this way. At what point did you start feeling like an imposter? Was it when you went to college or high school? When you didn’t make a sports team? That’s stuff you have to work through. I feel like we have to go back and dig it up. Whether it’s therapy—however people want to deal with some of the things that happened in their young life—deal with that. It doesn’t have to be a big trauma, but deal with it. Then learn to walk with your head up and your shoulders back. Talk to yourself better, get people around you who think you’re a big deal. You don’t know how many people are in your corner until you remove yourself out of your own way.

The book plunges you into your life, and you capture these really specific moments—whether it’s in your job interview with the First Lady or getting ready for a visit from the Pope—that make the reader feel they’re right alongside with you. What went into figuring out what details to include to make those scenes come alive?

For me what went into it was how can I not break the trust and privacy of the Obamas. I’m very intentional. I don’t talk about anything personal. That’s not my business, that’s not my life. That was really top of line for me. I really wanted to focus on my story, but my editor would tell me, “People want to smell what’s in the room.” I remember reading a book called Somebody’s Daughter by Ashley C. Ford. I love that book so much. She was so vivid about her grandmother’s room and the doilies and the way it smelled. I swear to you, I felt like I was in my grandmother’s room. For me, I wanted readers to think in their mind, “I can picture this room.” It sounds so nuts, but that’s why I tried to describe everything in detail. I want you to picture what it was like, I want you to feel what it’s like, I want you to see it. If I just said “the Blue Room in the White House,” people would be like, “What do you mean? Is it blue furniture? What are you talking about?” Most people won’t go inside the White House. Most people won’t look up what the rooms looked like. I wanted people to have that feeling that they could be in the story. That really was important for me.

Something that you’ve shared on social media is how you’re part of this cohort of 2024 debut authors, where you’re all very intentional about sharing and promoting each other’s work. That seems to be another piece of the importance of community for you. Can you talk about your involvement with that group and how that came about?

It came about because I was having a hard time writing. I needed help in the sense of community. I just felt so alone and I didn’t know who to ask. I have friends who are writers and I would ask them questions, but I needed a support group. I need community, and I think whenever I try to do something by myself without community, it’s so hard. I reached out to my agency. They have an author, Karen Tang, and they said, “I think she’s part of a group.” She added me to a Slack group called 2024 Debuts. I don’t know how many people are in the group, but it’s broken down by announcements and there’s a BIPOC channel and there’s a DC/Maryland/Virginia channel and there’s an LGBTQ channel. It’s so supportive because you can ask the question, people answer, but you realize we all are going through the same thing. Part of what we do is that we try to lift each other up with the books. But we share this because it’s hard. I’ll do whatever I can to be in community. Audre Lord’s ninetieth birthday was last month. I gathered a bunch of Black women who either wrote books or are coming out with books for a dinner. We need to be there for each other because it’s really hard. Harder than I ever thought.

Wasn’t that an event where you didn’t necessarily know everybody ahead of time?

I slid into people’s DMs, child, I slid into people’s DMs. (laughs) I was just like, “I know you don’t know me,” and I would send them a link to my stuff so I didn’t seem out there. “This is my website, you can Google me, and I’m having this dinner.” I tried to focus on Black women who also were writing comics, fantasy, romance, YA and thrillers because I feel like we don’t give them as much support, because the genres for Black women steer so much in the self-help and memoir lane. There are these dope women that are doing fantasy novels, right? Let’s bring everyone together. That’s what I do.

Finally, what role has the library played in your life?

For me, it’s almost like CandyLand, you know what I mean? I love candy, and it’s like walking into one of the stores that has penny candy with so many selections, and they’re all satisfying. You’re like, “What can I get today?” The library’s where I got my love of Choose Your Own Adventure books. I loved those books because I feel like they took me to a different place, you could escape to anywhere, and it was free. I’m old enough for the Dewey Decimal System, and I remember being so excited when I would write down the numbers and go to the shelf and find that book. It was almost like a treasure hunt. For me, the libraries provided a solace. They provided me a way to escape and discover literature, and also music as I got older.  I’m dating myself with CDs, but I would check out CDs I couldn’t afford. Before I got a computer, I’d go to the Cincinnati library all the time and use the computers. It was only a half hour slot, and I would just go to the first floor, then go to the second floor, and just sign up for all of them. They weren’t connected so nobody knew that I was already on the first floor. (laughs) It really helped me just get on the computer. I had my first tech experiences at a library. It makes me sad the state of where it is now, because the librarians I’ve always encountered, including my really great friend Tim in Ohio, they just want people to read. They’re people who are there just for the love of reading. 

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