all photos: Lexie Moreland

January is all about reinvention. So, it seems fitting, that a few days before her fortieth birthday, we got to sit down with Deesha Dyer in New York City to talk about the whirlwind nine years she’s had since landing a job as an intern, and then social secretary, at the Obama White House. To say her career path has been non-traditional would be an understatement; a native of Philadelphia, she graduated from the Milton Hershey School, and would later drop out of college to work odd jobs, eventually resuming her studies at the Community College of Philadelphia. We spoke about her tips for pursuing higher education smartly and affordably, how she was able to land the gig in the White House and what it was like to work for the Obamas, things that drive her (then and NOW) and how to stay hopeful and positive in 2018 and more, so read up on all of that below, and be sure to follow Deesha on IG and Twitter to stay in the know about all her latest projects and speaking engagements.

BYT: Lets dive right in. What did you imagine you’d be doing career-wise as an adult when you were growing up? Anything like this?

Deesha Dyer: It was interesting, I actually just put this on Instagram today; when I was growing up, I didn’t really think about what I wanted to be, probably until high school. When I was little, I joked around that I might like to be a teacher or a nurse, those sorts of stereotypical jobs, but there was a TV show called Murphy Brown that came on, and I wanted to be her. I thought she was amazing! She was a single mom who had this thriving career as a journalist, and I thought she was amazing because she wasn’t married, and had a child and a successful career. So I thought, “THAT’S what I want to do.” But I went to a school that was very rooted in family values, and they were like, “You need a husband.” I thought, “Why do I need a husband?” So I think I started there. Also, I’ve always really loved talking to people and listening to people, and there was a moment where I thought I wanted to be a psychologist, and then I got a D in psychology my first year of college, so I thought, “Maybe not.” Then I was going to be a teacher, and when I went in with my friend (a teacher) to one of her classes, there was a lice outbreak, so I thought, “Fuck this! I can’t be a teacher!” Then… I kind of just stopped, dropped out of college and did a bunch of odd jobs until I went back to school when I was thirty.

BYT: Right, and there’s been a lot more discussion lately about what is the right or wrong way to pursue higher education, especially because of the massive amounts of student debt people face. Since your trajectory wasn’t “traditional”, and your success goes to show that people don’t necessarily need to follow a cookie cutter path, do you have any thoughts or advice on this subject?

DD: It wasn’t until I hit my thirties that I realized how important education was. I think people should go to college, but I think what they don’t realize is that you don’t have to have it figured out as soon as you graduate high school. You’re seventeen or eighteen, leaving your parents’ house for the first time, and you don’t even know what the world is like or what’s out there for you to do. So my advice is for people graduating high school, and contemplating going off to college, is to go to community college first to start your general requirements.

First of all, it’s a lot cheaper, and second of all, you still have to get all your classes done and over with. When I graduated Community College of Philadelphia (I was at the White House at the time), I got a whole bunch of letters from other schools where they had partnerships, and so I had full rides to really good schools, simply because I did well in community college. And in community college, I had a payment plan. So I walked out with no debt.

I think that’s what people don’t realize – a lot of the stress of college is finance, and so if people can go to community college and discover what they like, go volunteer to see if they like things, I would advise that. Unless you’re dead-set on a career, you need time to figure it out. I just wish I knew that back when I was graduating high school, because it (community college) didn’t seem like an option then. I don’t even know if I knew it existed at that point. I know almost nobody that could straight up afford college; everybody had loans, everybody had debt, and while people did and do make their own way, if you can do it easier, that’s what I’d advise.

BYT: Yeah, I wish someone had told me that, too! Now, what was the moment in all of this that you decided to pursue an internship at the White House? 

DD: I used to mentor young girls in Philadelphia, and I used to get information about scholarships and internships and other little things to pass onto them, and that’s how I saw a White House internship application.

Before that, I wasn’t into politics, but I think I was mesmerized by the Obamas and what they were talking about. It felt like fresh voices, fresh faces, fresh everything, and that really got me engaged to the point that I was reading and looking things up on my own. I just wanted to be involved, so I’d to the local office and ask for ways I could volunteer. I can just describe it as a time that it felt like everyone was in unison. Maybe it’s just because I was in my own little liberal world that I wasn’t thinking about people who didn’t like Obama. Everyone came together to elect this man, and there seemingly wasn’t this tension between race and gender and sexuality and disability. It was an awesome time.

I didn’t do that much work on the campaign, because I was working so much, but once he got elected, I had his picture on my desk (I was a secretary at the time), and I was just like, “I want to work for him.” When the internship application came across, I looked at it and thought, I’m in community college, I’m thirty-one. I don’t think I’m going to get this, but I’m going to try.” The application was fairly easy; it was mostly writing essays, and I was a hip-hop writer on the side at the time, so I felt like I could easily complete the application, and then I got accepted.

It was a total, “What?!” moment, like, “Where am I going to live?! What am I going to wear?! Are you sure?! Have you done a background check on me?!” But I think that was my in; I didn’t know how I was going to get in, but I thought, “I’m going to volunteer every time he comes to Philadelphia. I’m going to get in front of them, because on paper I don’t look that impressive, but I swear, if they meet me and see my drive, I can do this.” And that’s what ended up happening!

BYT: That’s incredible! So what was an average day in the White House like for you? Or was there an average day in the first place?

DD: As a Social Secretary, which was my last two years (I went there as an intern in 2009, and then I got hired in 2010 and did different jobs here and there, and traveled with them), an average day if we didn’t have an event was usually waking up, getting into work around 9 o’clock, and just reviewing all the events and invitations we had for the next three months out or so. I’d go over all of this information with the social office team, and the Secret Service, and the communications team, and it would be all meetings all day. I was on the phone all the time, either to track down event information, asking the Obamas what kinds of food they wanted, which musicians, etc. So a lot of the time it was getting on the phone to negotiate budgets, because it was taxpayer money, and we couldn’t just say, “We want this artist, and we’ll pay $70,000 for them.” It was like, “If you’re coming in to do something on behalf of President, let’s figure out a way we can do this without it being an arm and a leg. You’re a multi-million dollar artist, and I’m sorry I’m asking you to do this for pennies, but it’s taxpayer money.” So the negotiating part of it could be tough, but that was an average day.

And then on the day of the event in question, we’d do all that, but we’d have to get ready for the event too. Two hours before we’d work on getting the decor up, then all the guests would arrive, the Obamas would come, we’d brief them, they’d go to the event and then leave. The events started to run like clockwork after a while with the exception of a few, the Pope was obviously a different situation. But meetings, phone calls, memos and decisions were more of the average day. And also creative strategy, asking questions like: “How can we do something different? How can we do this last state dinner, or this last concert?” Some things are very much in line with tradition, and they stay the same, but we tried to mix it up when we could.

BYT: Did you have any favorite moments over the course of your time there?

DD: I always say the Pope, but that’s a pretty predictable answer. We did a lot that was wonderful and memorable and special, but I’d have to say (and it’s because it happened a year ago today according to my Facebook memories) surprising Vice President Biden with the Medal of Freedom, and he had no idea because we’d kept it a secret, was definitely a highlight. Seeing him and all his family be so emotional was really special. It was a good way to go out for us.

But also things like the Brown v. Board of Education anniversary, the Smithsonian National African American Museum…I brought in a marching band to do a show on the lawn, and the people were asking: “You’re doing what?” And President Obama was like, “I don’t know…okay, we’re going to trust you, this sounds great.” And all I could say was: “I swear, this is going to be great, ma’am!” And I remember she was getting her hair and makeup done for the event, and her aides told me that she came out when they were practicing, and she her reaction was: “Oh my goodness!” So… that was pretty cool and fun.

BYT: Well, things are decidedly less cool and fun since the changeover. Just for an average person who wasn’t directly involved in the previous administration it’s been incredibly tough, so I can’t even imagine how this transition has been for you…

DD: I worked the last day, January 20th, and I was one of the last people to leave the building. I slept in my office the night before, and I remember I put my pajamas on and brushed my teeth in the bathroom, and I thought, “I’m going to go walk around the White House in my pajamas.” So I walked around one last time. It was really quiet, and you could’ve heard a pin drop. There was a weird vibe in the air that the house didn’t belong to us anymore, and it felt that way.

The next day we woke up at the crack of dawn, and there’s a tea that happens at the White House with congressional leadership, and it was hard, but it was still my last event, and I knew I had to make it stellar. I was focused on work, and I think it all became real when we had to put them in the car in front of the White House to go to the Capitol. They did the tea, all got in the car and drove to the Capitol Building together, and I think that that was probably the hardest moment, because number one, we were running late, and I was mad because it was my last event, but also, once the cars pulled off, I knew that the Obamas weren’t coming back. And seeing them say goodbye to all the butlers and chefs and the residence team…that was really hard. And then me saying goodbye to them was really hard. As soon as they left, the transition team comes in and starts preparing the house for its new occupants, and for the parties they’re going to have after the Inauguration, and I just looked around and thought, “I basically have to get out.” So I went and turned in my badge and walked out. We all got on the bus, probably twenty or something of us, and then we went to the hangar where Mrs. Obama addressed everybody at Andrews Air Force Base.

It was an eerie feeling, but it also was a feeling that it felt like it was time. It couldn’t have gone on a day longer. And we always knew January 20th was coming. We obviously didn’t know what the outcome of the election was going to be, but it felt like it was time, and once the Obamas got in the car, I thought: “That’s it. My bosses are gone, the people who lived here, and now it’s turning over to another family. It’s still the country’s, but I don’t belong here.” So I got my stuff and got out. I thought it’d be a big emotional thing, but I just got my things and went. I haven’t been back since. I think about it a lot.

BYT: I feel like everyone has been trying to navigate ways to stay positive and to resist on a day to day basis, but do you have anything specific you’ve incorporated into your routine?

DD: Number one, something I have to do is not get so cynical when I look at the work that we did and feel down. I have to remember that we did what we were supposed to do, and we did it to the best of our ability, and it was an honor to serve the Obamas, and also the country, but we did the best we could with the time we had, right? To try and not look back and think, “Oh my god, they’re ruining everything we did!” It’s just, you know, you can overturn policies all you want to, but the hard work and the heart that we put into what we did will always remain. I think I don’t allow the new administration or whatever else is going on to dampen my experience at all. To me, that’s the first step.

The second thing to remember is that I’m a citizen; I was always a citizen, and even before I was at the White House I was a social activist. People will say, “You’re so vocal about stuff now!” But I was always that way.

My rebellion (resistance is a very soft word for me, so I use the word rebellion) is needed right now, so that’s where I fall in line. I’m not trying to start anything new, but I’m trying to join groups and communities and say, “What do you need? Where do you need me?” And it’s whatever I feel strongly about. Right now it’s Black women and girls and sexual assault. “Where can I fall in line with being supportive to you?” There are groups that are out here doing all this work, and they’re killing it! And these youth now! These kids are so woke these days! That fires me up enough to stay positive. And I think that that’s honestly how I make it through. It’s really hard, like this morning I woke up and saw the news and thought, “Every day it’s something,” but I also look at it like, in the end we’re going to be okay because we have to be okay. I don’t know how that’s going to end up, but we’re going to be okay. Also being here at Ford, an foundation that gives money to communities that are doing social change. Knowing I work in a place like this, where they give money to somebody on the ground that’s doing something on behalf of internet freedom or equality or child marriage or whatever it is, that’s a good feeling. So I’m contributing where I can, and that’s how I really make it through. And yoga. And lots of sleep. [Laughs]

BYT: You’ve also been very active with your organization to help teen girls travel! Do you have any tips for people (teens or otherwise) for how to broaden their horizons even if they’re not able to hop on a plane or a train?

DD: Of course! Thanks for asking, that’s my heart. It’s called beGirl.World, and I run it with one of my best friends out of Philadelphia, Marcella, and we started it in 2014 when I was still at the White House, but I wasn’t able to focus full-time on that since I was working. So Marcella really took the brunt of that and helped run it. When the White House ended in 2017, I was able to take it over full-time. Every two years we have twelve to fourteen girls, and they’re high school girls in Philadelphia, and we take them through a two year program. So the first class was 2014-2016, and they learned about culture, they learned about different foods, about study abroad, about foreign exchange, foreign service…so everything in travel and travel careers. They learned how to use the resources to plan trips: Expedia, Airbnb…they learn all that, and then at the end of the program we take them on a trip.

In 2016 we went to London and Paris, and we just started a new class (we took off a couple of months to regroup), and these girls are amazing; they’re all freshmen and sophomores in high school. In 2019 they’ll go on their big trip. One thing we don’t do is travel shame. Instagram is very good for showing people who went to Morocco, and it’s beautiful, but not everybody has that, so we tell the kids things like, “If you live in Philadelphia, you can go to New York, and that’s traveling. You don’t have to get on a plane. You can get on anything and you’re traveling.”

We really want to plant a seed in them so they’ll have a sense that they are part of a global community, that they have the option to do what they want to do, whether it’s going to Brazil and study, or working in foreign service. Black study abroad and foreign service have very low numbers, so we just want to present them with these options so they know what’s out there. Communities that want to get involved with beGirl can. You can throw a passport party with music and food, and we’re going to teach girls to fill out passports, and we’re going to raffle off a fee so they can get a passport processed for free. Or have an Asian night where you teach them how to make sushi, or go to the airport to meet with a pilot.

We tell people to just explore what’s out there; everything’s global. It is just important to get started.

BYT:That’s great! And what are you excited or hopeful for in 2018?

DD: I’m hoping there’s a candidate that emerges on the Democratic side that we can all start getting behind now. That’s number one. Number two, I’m hoping to be very involved in the 2018 elections, and I’m hoping to be able to go to Idaho or California or wherever’s needed.

I remember how November 2016 felt, and having to go into work the next day, and having to welcome the Trumps to the White House the following day. And I said to myself, “Remember this feeling when it’s time to work.” So, I’m hoping I can fall in line when it comes to the candidacy in 2018, like, “Where do y’all need me? Putting up signs? Throwing parties? Wherever I’m needed.”

I’m also hoping that the narrative of Black women comes to the forefront more, all the stuff with sexual harassment and assault, especially as it applies to poor Black girls. I’m hoping to start looking at that narrative more, and that we start to equate R.Kelly (the singer) to Harvey Weinstein; we should be in front of his house and his concerts. I’m hoping that comes to the forefront more so we can all have healing. I want more people to tell their truths. I’m just excited to see all the community organizations still doing their thing. It’s unbelievable, and we don’t see it enough the good work that people are doing with their own resources. And there are a lot of people like that. We’re good people, we really are, but right now, it’s being controlled by crazies. Everywhere you go there are crazies, and I’m hoping people realize how important local elections are in 2018.

BYT :Absolutely. And finally, what fuels you? What drives you to get up every day and want to be the best version of yourself?

DD: I don’t have any kids, so I think my nieces and nephew. They’re biracial, and I know they’re watching me and watching what I do. They look at me like their woke aunt; I’m the one giving them activist books for Christmas, and I’m like, “You’ll understand this when you’re older, but you’re not getting toys from me!”.

They drive me a lot, and I worry about them a lot. I worry about them being Brown, especially my nephew. I want him to understand the dangers of being Black, but also the dangers of patriarchy, and I want to understand his responsibility to protect women, to protect his sisters, even though he’s the youngest, and to protect all women if he sees an injustice. You know, when he goes to college, or in high school, that he doesn’t participate in that behavior. I’m really hoping if he doesn’t listen to me then he watches my example and what I’m involved in, because it would just crush me otherwise. But he has a responsibility, so it’s not just about him getting pulled over and the police doing something; it’s also like, you have a responsibility to call out when your friend is touching a woman’s butt or catcalling or doing anything like that. You have a responsibility to say something. That drives me.

I think that food (I’m obsessed with food) drives me.

And the truth. Not just women, but men’s stories, too. The men that are coming forward to talk about how they were assaulted, too…I want people to have their own comfort level; if you don’t want to talk about it, that’s your own business, but people that are telling their truths about that (and anything), it’s comforting, because you think you’re the only person who goes through stuff, and it makes you more open to talking about what you’ve been through, and to heal and to help other people.

I think people coming together and sharing and being honest with each other is really what drives me, too. I just had an Elle article come out yesterday, and it’s probably one of the most honest ones that has come out, and it talks about how I was pregnant. I had an abortion. That’s actually public; I wrote about it years ago, before I was even at the White House. But people have said, “I went through that as well!” And you don’t have to tell your business, but I want people to know I was a Social Secretary and I have real fucking life issues that came with it. So I’m hoping they’ll be motivated enough not to let what they’ve been through feel like a stopping point. Like, “I went to jail, so now I can’t do this,” or whatever it may be. You can. And so I’d say that what fuels me.