Welcome to UnF*ck Your Brain. I’m your host, Kara Loewentheil, Master Certified Coach and Founder of the School of New Feminist Thought. I’m here to help you turn down your anxiety, turn up your confidence and create a life on your own terms, one that you’re truly excited to live. Let’s go.

Hello my friends. We are having a conversation today about a lot of things, but especially about a word that I would say comes up a lot in coaching and people are using it without necessarily really thinking through what it means. And that word is authentic and authenticity, which I feel has become a very popular buzzword. And we could all use it to have a better kind of understanding of what that means and what we’re talking about when we talk about it.

So, I’m super excited to be here with Deesha Dyer, who has an amazing resumé and has worked in the White House, has a book which has possibly the best book title I’ve ever read called Undiplomatic: How My Attitude Created the Best Kind of Trouble. And if you know me, you know that I’m all about women and other marginalized people making some trouble, so I’m excited to talk about this. So welcome to the podcast. Can you tell us a little bit about your journey, how did you end up working in the White House? What led you to write this book? Give us your life story.

Deesha: Yeah. So, first of all, thank you so much for having me here. It’s such an honor and I’m so excited to talk with you. For me, writing this book was definitely not something that was on top of my radar, but neither was working at the White House. And so, I had dropped out of college when I was 17. Went back to college when I was 29. The only college that would take me was community college and that was around the same time Barack Obama was running for office.

And I was a big community advocate, but I wasn’t plugged into politics. I wasn’t plugged into the elite part of politics. I was kind of just like, that’s government and that’s not what I do. I do activism. And then this man started to appear everywhere and I was like, “I really like, who’s this person?” And God bless his heart, he’s definitely not going to win. We’ve never seen a Black president and so, lo and behold, he won.

And right after the election, I got an application for a White House internship. And someone asked me to pass it along to the youth in my community who were in college. And I was like, “I think I’m not going to do that. I’m going to apply for it myself.”

Kara: I’m also in college, this is perfect.

Deesha: I’m also in college, so I know that there’s a 10 year difference but I’m still going to do it. So, I filled out the application, got the White House internship in the fall of 2009, Barack Obama’s first year. Then got hired back at the White House in 2010 and then just stayed there till the very end through several promotions to get the top job of social secretary, which is running all the parties and events and state dinners and all that stuff. But the whole time I was there, I was like, “What am I doing here? I don’t belong here. This is not my jam. This is not my thing.”

But I kept excelling and so Undiplomatic takes people through that journey. And it also takes people through, it wasn’t that I got a job at the White House and I was so confident. It was definitely, I’ve got to figure this out because my physical health is being impacted by me feeling like I don’t belong and so that is really what the book is about.

Kara: I feel we could have a whole podcast episode just about this, the last two minutes of everything you said. So, first of all, I mean, I love the story of you having dropped out of college and then coming back ten years later. So many people I think, think, well, something went wrong or I made a mistake or my life went off track somehow and now that’s it. The number of people that I coach, literally from ages 18 to 80, who are telling me, “It’s too late. I already screwed it up.” People have that thought at every stage.

So, I’d be curious before you even kind of get to the meat of the book, what was your thought process? Was it hard for you to go back to school? Did you have to change that kind of thinking? What was that like for you?

Deesha: Definitely. I mean, for me, I’d always wanted to be a social worker, and I thought that just because I was a nice person who cared about people, that I could go help people. Why do I need a college degree? And so, I think, eventually when someone was like, “You actually have to go to school.” I was like, “What?” That is why I started going back, really, because I know what I want to be now. It’s completely unrealistic to be 16 and applying for college and being like, “Oh, I want to be this, or I’m going to stick to this.” I think it’s an unrealistic expectation that we ask of our kids.

And so of course, being a psychologist at 17, saying, “I wanted to listen to people’s problems,” was not correct. And so, when I eventually went back to school, it was simply because I’d finally figured out what I wanted to do, but no school would accept me. And so, I had to go to Community College of Philadelphia in order to get into a four year college. And it was amazing because I’d never looked at community college before because I was like, “It’s a 13th grade, it’s junior college. It’s for people who aren’t smart.” But it was the best decision ever for me. So, it was amazing and it was wonderful.

Kara: My husband also had a kind of misspent youth in some ways. I’m not saying that’s what you had. That’s just what happened to him and had dropped out of a couple of colleges and then went back to community college first and then became a lawyer. But community college was also really big for him to get him back on that educational path.

Deesha: Yeah. It was the best, it was time slowed down. It was my pace. It was just really great for me. Four year college wasn’t, I didn’t have the discipline for that at 17 or the money, so yeah.

Kara: Yeah, which makes sense. Okay, so let’s talk a little bit about your book and let’s talk about authenticity. So, you say in the book, authenticity is more than a buzzword, which, yes, I want it to be, yes. Can you tell us, what does authenticity mean to you?

Deesha: I feel authenticity means living in the truth in the present time that you are in. So, I think that we often look at it as something that we get when we’re four or five or whenever we start having consciousness and we have to stay that way, true to myself, I’m going to stay true to myself. And oftentimes people look at that as true to themselves, I’m not going to change for anybody. But you’re growing older, you’re maturing, you’re having different experiences.

So, your authentic self is going to change with different situations. And how I act with my family, I’m not going to act the same way with my girlfriends on vacation. You know what I mean? It’s not inauthentic, it’s just that it’s a different circumstance. So, I think that sometimes we say that and it’s making people, I think, feel stuck in a space because they are looking for, this is how I have to be at all times. But no, you should change and it’s okay to change as you are. So, authenticity is how you are in the present moment and being true to yourself due to the environment around you.

Kara: Yeah, I love that because there’s this idea, I’m a fixed static self through time and through different situations and that’s the real me. As if it’s a rock you can discover in the forest, that’s a real concrete thing.

Deesha: Yeah, exactly.

Kara: But really the question isn’t, am I being exactly the same every moment? Because nothing in life is consistent, no animal is consistent that way. But what are the motivations behind how you’re acting? Are you acting differently because you’re hiding who you really are or you’re uncomfortable with yourself or you’re people pleasing or you’re not comfortable showing up? That’s such a much more interesting question. Why am I being the way I am in this scenario not, am I being my authentic self?

Deesha: I completely agree with that and I love that outlook on it because I also feel it’s one of these things where you start to feel, I feel maybe with maturity, you start to feel in your gut. And maybe it’s not you, it’s just the environment. Perhaps that’s just not the place that you could be yourself. So, then you have to make a choice, do I want to keep pleasing these same people in this environment? Or do I just want to get out of it? So, the question even on belonging, I don’t even ask. So, I’m just like, “If I don’t belong somewhere, maybe it’s because it’s not for me.” Not that the environment’s bad, but it’s not my vibe and that’s cool.

Kara: It’s not a match. So, you worked at a place that I imagine had a lot of structure. There’s ways of doing things in a White House, and anybody could look at either of the Obamas and tell they ran it like a tight ship, probably. So, I’m curious, what was your experience with being somebody who’s like, “I want to do things my way,” and then being in a place that had a lot of rules and structure, what was that like?

Deesha: Yeah, I would say it was 50/50, hell and heaven because the hell part was that I didn’t come from the political world. So, all the decorum stuff that you need to know or you should have or even who the donors are or who the players. I had no idea who these people were. I was like, “I don’t know who you are.” So sometimes I’d have to ask a lot of questions or I’d say, “Well, let’s do it this way because I don’t really know the traditional way of doing it.” Which then was the heaven part because I got to do things in a non-traditional way.

I got to be undiplomatic, I got to be like, “Well, why don’t we trial having a live band outside of the White House?” And people were like, “What?” And I’m like, “I don’t know, I think that sounds like a great idea to me.”

Kara: If it’s fun, what’s the problem?

Deesha: What’s the problem. They’re like, “Well, usually we have a string organ.” And I’m like, “That sounds lovely, but let’s give local musicians a chance to maybe just play their guitar.” And the heaven part was the Obamas gave me the authority to be like that. They were just like, “We trust you.” And I was like, “Okay, are you sure?” So that was the great part because I had these two untraditional people that were just like, “We’ve never been here either, Deesha, let’s just do things different.”

And so, it was hard, I think, many times because I was going against the grain. And then also you have to realize, if you do your own thing and you’re so in tune with yourself, people don’t like you. And so, I had to be like, “Well, I’m not going to be included in this fancy event or this, whatever, happy hour because here comes Deesha.” So, I’m like, “It is what it is.” So, I’d say it was a 50/50.

Kara: I’d like to talk more about that because I think I’m often teaching similar to what you’re saying. It’s more important to be yourself, to show up as you are, to resist these kinds of oppressive structures. And then of course, a very natural response is, “Yeah, but there’s consequences for that sometimes.” You can negotiate at work and then we have the studies showing that women and people of color when they negotiate may actually decrease their compensation. Or you get this boomerang effect of the sexism or racism or whatever else from the other side.

And a man’s assertive and a woman’s a bitch, all of this kind of thing. So, I’d love to hear kind of what are some actual tips you have for listeners to try to bring their whole selves in even when that’s not the status quo, that’s not what people usually do. And how do we think about the risk reward of there potentially being consequences when we do that?

Deesha: Yeah, I think it’s a great question. When I think about the risk, I’m very upfront and honest with people because people look at me and they’re just like, “You’re so yourself and I love that you’re a truth teller.” And I’m always extremely honest and say, “I want you to know there are consequences to that. The consequences are, we love being in group activities and being in community, sometimes I’m excluded from those things.” People talk about me and sometimes it’s like, “Here she comes.”

And I have to be okay with being talked about because at the end of the day, I know that I’m going to bed, being like, “I did the best that I could for myself and my community.” And you have to know that it’s a long game. You’re going to feel better about it a year later, opposed to the time right then and there. And so, I think that for me, that’s what I have to tell myself. And I give people the advice of, “You have to be okay with finding that group that’s for you, that may not be your co-workers. It may be a different department, it may be outside friends.”

And so, I think that being yourself will always pay off in the long run. But you have to be willing to understand that it will be a little lonely sometimes. And as long as you’re okay with that or you have other things to fill that in, then you should always bring yourself. But I’m also understanding that I also speak from a place of privilege, I work for myself. Not everybody has that. So, I don’t ever want to give that advice to people and them say, “I need my job. I can’t afford to do that.”

So of course, in the safety of financial, physical, mental, do what you need to do, but make sure that you have therapeutic things outside of that to remind you of who you are. So, you don’t adopt this philosophy of, I’ve got to fake it, I’ve got to be somebody else.

Kara: I think also the thing I’ve been thinking about a lot is that there is a little leap of faith required in believing that if where you are isn’t the right fit for you, that there are other options. I think about this a lot with, well on a lot of different fronts. But I think one of the most insidious things about socialization is it not only tells us who we’re supposed to be and who we’re not supposed to be, but it also makes us think that everybody shares this belief, so everywhere is the same.

So, if one job, if one boss doesn’t think working moms do a good job, there’s no point in trying to go anywhere else, everybody’s going to think that. And it’s so pervasive, I mean, I think it’s true along so many different identity elements. And so much of the work is being, so when I was dating in New York as a fat person and seeing every single fucking, profile is no fatties, height and weight proportionate.

So that’s real and I just need to believe, okay, it can’t be possible that everybody thinks this. Fat people have been having sex since the beginning of time, there’s going to be some people. And the same is true in your job, whatever it is. So, I think that we’re never about, well, not on this podcast, never about denying that there is a risk benefit scenario of showing up as yourself and your identity and not doing all the code switching that’s usually required. Or not get it going along to get along or not conforming.

But make sure when you’re thinking about that risk reward scenario, you’re not taking the oppressor’s story about what’s available to you and what the options are to you. And just believing, okay, nobody will accept me if I show up as my true self. No job will want me like this. No man will want me in this body. Because otherwise it’s such a reinforcing cycle. You’re in a bad place or a bad spot, and then you’re like, “Well, I have to stay here, there’s no other option.”

Deesha: Right. And I think that’s where imposter syndrome often gets it wrong. And I always tell people, it’s a delusion because we do adopt in that situation, the oppressor’s thoughts about us. And not only do we adopt them, but then we make it our fault. You know what I mean? It’s my fault, I can’t date in New York because I’m Black and all the people up here, they want light skinned women. You just start to be like, “But I wish I was, well, only if I was.” Instead of being like, “This is just the way I am and I can’t change that.”

And honestly, I don’t want to. I’ve never wanted to wish I was somebody else. Of all the things, I wish I had been born to a rich family, all these, but I’ve never wished I, in this body, in this skin with someone else. And I think that that’s where imposter syndrome changed a lot for me because I was like, “This is my fault and if I would have had more education, if I would have had this.” And then I’m like, “Wait a minute, I made it to the White House, what am I saying?”

Kara: Yeah. Where am I supposed to go from there? What else could I even be doing?

Deesha: Yeah, what else? And so that’s what I’m addicted to now is, what else can I do? How exciting is all of this. But I do believe that oppressive language is what kind of makes us turn on ourselves and beat ourselves up and talk mean and all those things. And I’m just like, “I’m not doing that crap anymore. I’m just not doing it no more.” So yeah.

Kara: So how do you think those of us who are managers now or who have gone up the ‘ladder’ a little bit or have more connections or have a little more power. How can kind of leaders of organizations champion their employees to be their authentic selves? What can you do, if you are a leader of people or manager or whatever else, to make your work environment more welcoming of people being their full selves?

Deesha: Yeah. And I’m going to say, something that I say and people, not laugh, but they’re always just like, “What?” But I always feel we as managers or leaders, we’re always looking at things that we can do to make other people comfortable without fixing ourselves. And so, I look at myself constantly and say, “Deesha, what community do you have your unconscious bias that you are putting into the world? Just because you are a DEI leader and you’ve done all these things does not mean that you are not being harmful to a community or to people.”

So, I think that the first thing as a leader is, get yourself checked. Figure out, what biases do I hold? How does that impact the people that I lead? And start there because again, we think we’re untouchable because we’re leaders of things. And I’m like, “No.” I’ve definitely had thoughts or actions against communities that I’m not proud of, but I need to work on that before I try to lead somebody else. I think that’s number one.

I think number two, having equal accountability throughout organizations. I think that oftentimes we talk about DEI and we talk about different things and well, we’re going to have trainings for that. But with sexual harassment and with other things, there is no training, you’re fired, you know I mean? And I’m not saying that everybody should get fired for stuff. What I’m saying is, we need equal accountability for when we make a workplace harmful. And being a leader that stands up and say, “We need to have that.”

But I think it’s also pouring into your employees all of the time, not just when there is a performance review and there’s a big project. How can I help them continuously grow? So, I think as a lot of leaders, is that we keep people in place so they stay at our workplaces. I love them, we just had somebody in my job, move on. And I’m like, “Oh, my God, my assistant’s leaving but she got a really kickass job. Good for you that you felt that empowered to move on.” And so, I think that us pouring into and making it an environment that people really want to be in versus one that people are just there for a paycheck.

Kara: Yeah, I love that. I think also I have been working a lot in my own leadership on being okay with conflict, allowing there to be conflicts. So, in our executive team meeting now we always say before we start, “We have permission for friction to advance our mission.” Our little thing we say because I think that especially people socialized as women and everybody’s personality comes into it. I wouldn’t say about myself, I’m non-confrontational. I’m very direct and honest.

But I’ve made a point of really only surrounding myself in my personal life with people who don’t fight, who have very calm discussions all the time, don’t have any conflict. That is my personal life preference and of course I’m not saying I don’t want people in my organization who scream at each other, but it’s just different. It’s a different situation. It’s not a personal relationship, it’s a professional workplace. I’m selecting people on a different basis and allowing there to be conflict without freaking out about that or making it mean something’s gone wrong.

I feel I have seen my leadership team, which are all women, two-thirds of which are women of color, blossom a little bit more into their full selves is allowing for that conflict and that not meaning that it’s bad, someone’s in trouble. So, I think that’s, especially for people socialized as women, how comfortable are you with allowing for natural friction to occur?

Deesha: Yes. I think that also having scenarios or phrases, just like everything else of how you approach that conflict because some people just don’t know and we just haven’t been taught. So, if I’m having an issue with a co-worker or whoever, how do I go to them without getting a personal feeling where they feel attacked?

Kara: Right. So many people don’t have conflict resolution skills in their personal life either, so they’re not going to have them at work.

Deesha: Yes, 100%. That’s something that I’m also personally working through just being from Philadelphia. I’m constantly like, “What are you talking about, what do you mean?”

Kara: Yeah, I’m from New Yorker parents so I’m just like, “No, bad idea.”

Deesha: Moving on, moving on. I said, moving on. So yeah, that’s a personal thing for me.

Kara: That’s why the podcast conversation has been so concise and to the point, because we’re both like, “Let’s go.”

Deesha: Yes, exactly.

Kara: So, everybody should obviously order your book, which is again called Undiplomatic: How My Attitude Created the Best Kind of Trouble. Where can people find you if they want to follow you, learn more about you?

Deesha: Yes, they can find me just, I have a website, deeshadyer, first and last name D-E-E-S-H-A D-Y-E-R.com But then I’m on Instagram actively, probably the most, it’s D-E-E-D-Y-E-R 267. On my website it says all the places you can buy the book. Of course, we love supporting independent, color bookstores and marginalized people, bookstores is also the Amazon and Barnes & Noble and all that on there. But it’s just exciting to have the story out there and it’s just great that people have been receiving it so well, so yeah.

Kara: Awesome. And we’ll put it all in the show notes. And I always like to say, if you really can’t afford to buy a book, go request it at your library. All of that helps with demand and showing institutions that people want to read this book.

Deesha: 100%.

Kara: Amazing. Thanks for coming on.

Deesha: No, thank you. Thank you so much.

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