Feeling Out of Place in Obama's White House

0:01This is a Global Player original podcast.

0:11Well behaved women rarely make history. Bloody difficult women do.

0:24that was a roller coaster just wait for when this guest tells me about the time she was in the white house organizing the pope's visit with barack obama and she had to have a sudden emergency abortion welcome to difficult women

1:03The plot of this difficult woman's life is political Cinderella story. The theme is imposter syndrome, how a girl who had a difficult childhood, an Apache education, ended up running state dinners for presidents in the White House. Yes, we are vibing with Deesha Dyer. And we're going to find out how an often excluded black schoolgirl became a hip hop star, writer and a sexual health activist, actually called the condom queen at one point, who applied for a White House internship and ended up the Obama's social secretary. What a story, Disha. Only you could have written him undiplomatic. I want to start with your childhood.

1:46Yes, of course. Thank you for having me. You are. I mean, this is such a great book. I so enjoyed it. The childhood was was complicated and difficult. You went to a boarding school where you you weren't shown a lot of love. You went to college and you applied to a college. You didn't get into Howard, which was the kind of cool place where you wanted to go to find your tribe. Anyway, so just can you give us a sense of your childhood? Yes, of course. And so, you know, for me, you know, my parents got divorced rather young. And there was a school called Milton Hershey School, which everybody knows as the chocolatier that was opened for orphan boys.

2:27And then they ended up expanding it to people that were basically from financially difficult backgrounds. And so my parents, my mom put me in the school thinking, you know, and I think well intended that it was, you know, going to be this amazing place for me to get an education, you know, stability, those kind of things. And it started out good. You know, I think as I was younger, I was excited to live with 16 girls and I had these new best friends. It was a boarding school. It was a boarding school. Right. So I stayed there. And that was fifth grade. I went. And then as I got further along into ninth grade is obviously when girls start the adolescence and menstrual cycles and all the things, the hormones.

3:08And and it just didn't vibe, I think, with with the school and the way that the school wanted us to kind of have a very centralized. This is how you have to be fit in the box for success. And so, you know, I was always kind of spoke up. I was always a bold person. And so I raised a lot of issues and, you know, went against authority a lot. And just, you know, that was seen as someone who was, you know, aptly difficult. Another theme in the book is attitude, your attitude and how you didn't fit within the box. You were a square peg in a round hole or whatever. There was one episode at Hershey where you were really punished for wearing the wrong shoes in church.

3:53And I just thought that was cruelty. Yes, yes. I was punished. And it was punishment. There was humiliation. So I was made to clean the wrestling mats after the wrestling team in front of the wrestling team, which was I was dating a guy on the team. And so it was very much a humiliation, you know, not just a punishment. It was, you know, it's beat you down enough to make it so you don't do this again. So, yeah. And would you say that you came away from education thinking that you weren't going to make much of your life? I mean, when did the imposter syndrome really start to bite? You know, I believe that it started to bite most likely when I was in high school, because that's when, you know, people start looking at your grades for university.

4:40And I was an average student, but I was very much more on the social activist, community leader aspect, which back then in the 90s, it wasn't valued. You know, now we have, you know, shirts and we celebrate it, but it wasn't, it was you are very, you're loud and you're, you know, you're boisterous and all these things that were negative. So I think that the imposter syndrome started to kind of be a conscious voice then, although I believe it was planted, way younger than that. Can you read this passage about it? I was led to believe that everything I had growing up in Hershey was solely because of luck, not because I was deserving of an alternative, stable environment and a good education.

5:22I was lucky to have a roof over my head, lucky to have food on the table, lucky to go to a boarding school, lucky to have clothes and shoes. It made me feel indebted to the givers of these gifts. I believe that I owed someone for my survival. Seeds of imposter syndrome were watered heavily in me at Milton Hershey School. You're an incredible writer. Thank you. And it's interesting that the seeds, when they're sown, you go through life and the seeds can be watered, But there's always the seed within. Yes, yes, yes. And that seed, you know, it produces roots. And then that roots produce a tree. And then that tree produces branches and leaves.

6:13And all of that is really how it all happened for me. Yeah. So then you went to university in Cincinnati. I mean, there's so much more we could talk about your childhood. But, you know, it must have, it was an unusual childhood because boarding school is not common in the States. and to have that separation from your caregivers at such an early age. There's a whole attachment theory around that, which we could talk about, but we've got so much else to get through. You went to college in Cincinnati. Yes, I did. I did. I went there, but I wasn't ready. I wasn't ready financially or mentally to go to college.

6:53I was 17. I wanted to have fun in life. I didn't want to sit in class. so yeah that so that lasted only a semester yeah you're you kind of were in real estate and you were in a rental with your dog I think yes yes making pasta sauce one night in a hot night yeah and you were in I think Philadelphia yes I was in Philadelphia and then you know I always think there are two or three one or two maybe phone calls or emails or texts that change people's lives. Do you want to tell our listeners about the call that changed your life? Yes. And so the college was about was about 18. And then this was a decade later that I was back in Philadelphia.

7:36And I got an identified number call. And it was from the White House internship program. Scheduling in advance was the department. And they were calling to do an interview with me for a White House internship in Barack Obama's first year, which was 2009. Yeah. And you'd sent off an application, even though you were pretty nonpolitical. You said you were swept up in the excitement of the Barack Obama Clinton administration and arrival at the White House, the first black man in the White House, the first woman vice president in the White House. So explain how you became slightly more politicized then.

8:16Right. So I think for me, it was it was really Barack Obama. You know, he was running against, you know, Hillary Clinton. And I had been a community advocate all my life. But it was the first time I'd seen that public service and politics intersect. I always thought they were so separate because politics to me was for people that didn't look like me. You know, whether it was just being a woman or a black woman or even somebody that was from a poor background, you know, that I wasn't connected. And so as I started to hear Barack Obama talk about, you know, just his life and his vision for the country, I became excited about, you know, well, I want to figure out how to work for him.

8:53So it had nothing to do with, for me, wanting to be in politics as much as it had wanting to work for this person that I saw so many common goals with. And then that's what led me to then apply for the White House internship. And I was back in school at that point. So that was a decade later. I was back in school at 30 years old. So, yeah. And then you went hell for leather to get it. Yes. I mean, you did the interview like then and there while the pasta sauce was cooking on the stove. Yes. I did it then and there and thankfully we didn't have Zoom then so the people couldn't see what I looked like um but I did the interview and and you know I was like that was a great interview but still the imposter syndrome was like you know but you're not going to get it this is so competitive and he's so popular that you know of course every Ivy League or every connected senator's son or daughter is going to be interviewing too so yeah but then you were picked and you and you and this This was an unpaid internship.

9:51Oh, it was. But your company, the office kind of really helped you on the way there. They did. The real estate company, not only did the employees do a fundraiser for me, I didn't know, but then the head of the company actually gave me a really nice sizable check. And this was after I accepted. This was after I found a very cheap apartment. And so I didn't know I was getting that money until right when I left to go to the internship.

10:34So you've got your stuff in a U-Haul. You had your box set of West Wing. Yes. I did. You arrive in the White House. Tell us what happened next. I mean, I arrived thinking that there would be a reason they would kick me out. You know, I thought they haven't seen me. They've got the wrong name. And so as I gave my passport to the Secret Service agent for the first day, he was like, welcome to the White House. And I was like, are you sure? You know, and from there I joined the cohort of interns. And in my department, I did the schedule and travel with President Obama. and so I assisted the staff in that which was amazing because I got to travel places and I got to you know get introduced to him in a different way that other interns hadn't and so that was a semester and then I left and then got hired back full-time.

11:23And I love the story of your first flight on Air Force One. I've heard about the peanut M &Ms were like branded with Air Force One but what do you remember when about of course you remember the president was still strolling around like it was his living room and he saw you. Yes, he saw me. The president saw me and he just, you know, got introduced to me and he said, I didn't know that interns, you know, were on Air Force One. Got to go on the phone. Because, you know, and he was saying it very candidly, very nice, not no problem. And I just casually told him that I'll jump off. I'll jump off. I was so tired and I was just like, I don't know what else to say to just get out of here.

12:00And he put his hand on my shoulder, as Barack Obama does, and said, it's great to have you here and just walked away. as he does. So at what point, how long did it take you to realize? And I think there's a line in your book which says, I wasn't the ideal candidate, but I was the right one. Yes, yes. How long did that take? I mean, honestly, it took all eight years, you know, to realize that. I think that it took me until almost the very end to say I did all of this with three promotions. I had this big visible job and they weren't looking for the perfect candidate. They were looking for the right candidate for the administration, for them and for the country at the time.

12:42And now looking back, you have made a huge career since you left the White House, which we will talk about. But just assessing the legacy of the Obamas, do you think the Hopi changey thing was only a thing? Or do you think it really changed America? What I would say is that it changed America at the time. I think that it is not as of where we are right now is that there is no sign that that ever happened. You know, I'll just say that politically. And that's the way I feel. I feel that it changed people in America, like individually, like myself and other people. But what I think is that as we get further away from it, I feel like it fades away.

13:26And it was a utopia moment in time that, you know, I'm not sure we'll ever experience or see again. And so I'm happy that I was there to live it and to help live out the legacy. Before we get into difficult times, I think everyone would love to know more about your day to day in the White House. I know you write very vividly about kind of getting your officeware from thrift stores and working out, you know, and the hotels and kind of managing your life and sort of all of your life being aimed towards facilitating their lives. and then increasingly their social life and kind of knowing who to invite and where to put them.

14:05I mean, how did you have the background, the chops to know how to do any of those things? Yeah, this is the thing I'll say, and I love saying this, is that I've always been an organizer. I've always been somebody who put events together. And so the fundamentals of what I had to do were exactly the same as when I did, you know, an HIV AIDS march in Philadelphia. You know, you had to get the right people. You had to make sure it was safe, make sure the press saw all the things. And so I had the fundamentals down. So what I had to learn was the diplomacy and the protocol part of it and the who's who.

14:36And that was something that had to be learned, just like everybody has to learn on a job. And so I was very lucky that I had a lot of great teachers. And I also had a record of the past social secretaries, all the work they did. And so I was like, oh, the Pope's coming. well the Pope came during Bush's years so let me talk to that social secretary and say how do I do this and she's like well here's the paperwork you know so it was a very friendly like you know people helping me but the elements and fundamentals of the job I always knew how to do it was just the kind of building on okay this is a new environment what do I have to learn about the environment not about so much the duties of the job yeah but also you had to kind of absorb a huge amount of political information really quickly.

15:20I mean, when you're giving a state dinner, and I think we will get to the Chinese state dinner because that was like one of the worst, most complicated times, I think, in your career there. But so before we get to that, what do you look back on and think, that was my pinch me moment? I hate that phrase. But when you thought that was amazing, I was there. I will say that the Pope visit, Pope Francis, because he was his first visit as Pope. He was a very popular pope. We had a very popular president. We had 12 ,000 people on the lawn. The weather was beautiful. There were no protesters. Everything was so great.

15:58I would say that once I looked on the stage and saw the pope and the president kind of swaying to the black gospel choir that I was able to bring in, that's the moment that I was like, oh, man, you did this, and you were made for this moment. So that, to me, was like my pinch me moment. It didn't last very long because I had the state dinner right after it. But I definitely, that moment was the moment I thought, I'm a hip hop girl from Philly, but like, look at what we could do. You know, like how amazing is this? And you're still a hip hopper girl from Philly. Still. I'm still, I'm still the same girl.

16:32I wear hoops. I still dance. I still listen to hip hop. I still do the same exact thing. Yeah. I know. You can't take that out of you. I can see it. And that's why you worked in their White House. You write candidly of a terrible health crisis and decision you had to come to at a time when a big, big event was coming to a climax. Yeah. And so during the right before the Pope visit, I found out that I was pregnant and I knew that I was going to not keep the baby. And but there was no time to have an abortion because the Pope was coming. And so out of all the times that I've ever, you know, that all the events that we've had for the Pope to come and right before that, me finding out I was pregnant, I think that was so difficult.

17:15And so kind of just like the stars aligning in a way that was that was just really like the timing. And I, you know, for me, the most important thing I took out of that was that's what woke up my imposter syndrome, because after I had the abortion, I took zero time off. I came right back to work because I was afraid that people were going to somehow say she's you know the people didn't know but they would say she she took time off why she taking time off and I think that for me is was my wake up call of like your physical health is suffering because you're afraid to put yourself first and so that is really what woke up my imposter syndrome but yeah that was that was a rough couple of days definitely yeah I bet it was and especially the fact that it was the Pope because you know what the Catholic Church has to say about the dilemma you found yourself in could not have been more stark.

18:09It could not have been. And I think for me, I was very lucky and blessed that, you know, I had Barack and Michelle Obama who do believe in a women's right to choose. And so did they know? No, I told them later. They found out later. But I bet they were super sympathetic. They were supportive of, you know, of course, like, you know, whatever you need, whatever time off you need. but I hid it for a long time because I was just like I just don't want people to think bad about me or you know she's this unmarried black woman who of course got pregnant and so I didn't give myself that grace and so that's what woke me up from saying like you gotta put yourself first your story I mean has the film rights been bought yet?

18:48no no I think right now people aren't touching anything political but hopefully in the future this is just an the arc of this is amazing the arc is amazing yes I hope so I hope one day Do you think that your imposter syndrome meant means I'm going to say present tense means that you you feel you can't bring all of yourself to that workplace or to work? Yeah, yeah. A hundred percent. But I believe that's for all of us, too. I mean, I think that we all have to compromise sometimes. You know, for the most part, I am very authentic into who I am. And, you know, that's what got me the promotions. That's what got me the accolades or the Harvard fellowship or anything else I've done is because I'm myself.

19:37Now, I will also say that I've also lost stuff because of that. I've also probably lost opportunities and I've lost, you know, here she comes. She's so she wants to talk about this and here she's so loud. But I have to accept that because I'd rather be myself and be a little turtle on the train of success than do it fast and not recognize myself at the end of the day. I mean, since you've stopped doing social stuff for the Obamas who are, you know, obviously no longer in the White House, you've done a ton of other stuff. You've done activism. You as you mentioned, you hold some sort of professorship at Harvard, which is fantastic.

20:15That's fantastically, you know, that's big. Yes. I mean, Harvard is. I know. Which is hilarious. Yes, it's fun. It's fun. It's a resident fellowship that I did. And then I sometimes guess go back and guess lecture. And you've written a book. I mean, you know, there's so many things you do, nonprofit stuff and activism. Where where now do you do you think your passion lies? That's a great question. I think my question, my passion currently lies in the mental health and welfare of people. I think that, you know, our world so much is happening that I'm not quite sure people are healthy, you know.

20:51So making sure that people have access to what's going to keep them well, whether that's medical, mental health therapy. And so I think my passion lies there, but it also lies in traveling and seeing the world from a personal perspective. And so I hope my next move I tell my husband is just so like, even before all the politicalness is like, just leave America for a while and live somewhere else and see what life is like. And so that's kind of like my dream as of right now. What's it like in America now? It's rough. It's tough. I mean, I think it's really hard. I think it's scary. You know, I'm very lucky that I have a great community and we have joy and we eat and we dance and we have fun.

21:35But I think dealing with the day-to-day unpredictability is very hard and very depressing. I also understand that I have privilege. You know, I have a job. You know, I'm making money. I have a husband. You know, I have these things. You have a roof. I have a roof, you know, so, you know, I'm sure there'll be a different answer from somebody who doesn't. But I would say that I it's it's a it's a really hard space to be right now. But you're you're still living in in the States for the moment. For the moment, we're living there. My husband's job is there. So we'll be there for a little bit. Yeah.

22:07So, yeah.

22:24I mean, people say that a lot of Trump's determination to become president in the first place and let alone in the second place was the roast at the White House Correspondents' Dinner when Barack Obama poked fun at him. Wow. I believe it. I believe that his election period, Barack Obama's election, was the catalyst to probably a lot of this, because I think that we are in a space where people that oppose Barack Obama will do anything to make sure that that does not ever happen again. And so that is what we're faced against. I think that had Barack Obama not been elected, I don't know if we'd be in this same space.

23:04We wouldn't have Trump too. At all. No. Absolutely not. Absolutely not. Sorry, that's the wrong way around. We wouldn't have Trump one, let alone Trump two. And there was obviously a personal animus between the Clintons and the Obamas. You know, the way Trump even just said Barack Obama's name, Barack Hussein Obama. And he would like emphasize his otherness, that whole Bertha story. I mean, America must miss the Obama's White House. Very much so. I think that we... Not just democratic America, but quite a wide swathe of America. I think that we just miss somebody who's just competent at talking in conversation or not making fun of people online and all of these things.

23:49I think that that's very missed. But when Trump does that, I think a lot of that is activating a base. And that's what it is. It's keeping them happy and keeping them entertained. But unfortunately, that entertainment comes at a consequence of a lot of people. lives and health care and everything else. And so that is kind of what we're dealing with is it's not really funny when somebody, you know, gets their benefits, you know, taken away for health care or food or anything else, you know, but it ignites the base and keeps people entertained. So it's going to keep doing it. Yeah, unfortunately.

24:26As we speak, Disha, Macron, he's in town for a state visit with his wife, Brigitte, and it struck me that the press the media attention that first ladies get is often horrific and some of the suggestions that have been made about Brigitte Macron echo some of the suggestions that were made about Michelle Obama these are both mothers of children and yet people say they're men you know that their husbands are gay I mean when you're inside the house, you know, living in the belly of the beast. What is it like when all this stuff is going on? How easy is it for you and your bosses to tune it out? Yeah, I think that for me, it was easier to tune out because it wasn't personally being said about me.

25:18But I would say that when I would see that reflected, you know, in, you know, Michelle Obama or her children or the president, you know, there was a certain, you know, I'm from Philadelphia, so there was a certain amount of anger that would rise in me and say, you know, I'll go fight these people. You know, I'm ready. Like, if that's what we're doing, let's roll, you know. But I think that they were truly the model of grace and patience. And never responded. Yeah, never respond. And she addresses this in her book about how it was. And, you know, she just says, of course it was horrible to hear those things.

25:54And it hasn't stopped. They've been gone for eight years and it still hasn't stopped. But I what I applaud is that she has a handle on who she is enough to say, I'm not going to believe what they say about me, nor am I going to put that on my children. And so just watching their grace and patience navigate that was, was admirable for me, really. And she gave a wonderful, a testimonial for your book. She said it was a must read. And I totally agree. Bring us up to date. Maybe should I on on the briefly the range of things you're doing now before we get to your difficult time? Yes. And so the brief the brief version is I run my own company called Hook and Fasten.