Sometimes, all it takes is one decision to change your life. When Deesha Dyer decided to bet on herself and applied for an internship at the White House as a hip-hop journalist without credentials, connections, and a college degree — she had no idea how this decision was going to change her life forever. After successfully completing her internship, she was promoted to serve as the White House’s social secretary during Barack Obama’s presidency where she often rubbed elbows with top United States and foreign officials.
In her new book,Undiplomatic: How My Attitude Created The Best Kind of Trouble, Deesha invites us into this pivotal time in her career and life as she defied all doubts, discovered the true meaning of self-love, and learned to break free from the little voice in her head telling her she didn’t belong.
Her Agenda had the opportunity to chat with Deesha in a candid conversation about her experiences in the White House and what readers can expect from her new book.
Her Agenda: You’ve had an unconventional and extremely inspiring career pivot. How did leveraging your passion for hip-hop and your journalism skills open doors for you later in your career?
Deesha Dyer: I applied for my White House internship in 2009, and the essay I wrote was about hip-hop. This was the catalyst. I started my career at the White House writing about hip hop and I kept my love for hip hop known the entire time I was at the White House. Eventually, this all came back to me in 2013 when I moved to the First Lady’s office and received the promotion to be the deputy which made me in charge of events and entertainment at the White House. So then it kind of continued from there. I had no idea that when I was a hip-hop journalist, it would have come back to help me.
Her Agenda: How did you work your way up from an intern to serving as the White House social secretary?
Deesha Dyer: The ignorance of not knowing how the White House worked really helped me out because I never really wanted to be in politics. I didn’t desire to move up. I wasn’t from a family or had a background of ‘climbing up the corporate ladder.’ All that stuff was new to me. I just thought, ‘these people seem very tired from trying to climb up these corporate ladders.’ I just wanted to have a good time and pay my bills. I was curious about things so I think as I got promoted at the White House what kept happening was I realized I loved doing certain things. I led with curiosity. It was never about the money because I was happy making money — period! I was really curious and thinking to myself this is really fun. So that’s how I moved up. It was never about climbing the ladder.
Her Agenda: There’s a lot of talk about higher education and college not promising jobs once you graduate. What are your thoughts on pursuing higher education as someone who started their career without a college degree?
Deesha Dyer: That’s a great question. I would love to go back to school now at 46. In my book, I talk about how I always wanted to go to a Historically Black College and University (HBCU) like Howard. I often think: ‘What if I apply now to go?’ I’m more mature, I know what I want to do, and I want to learn more – I’m in my learning girl phase. I do think the traditional way of higher education may not be for everybody. My advice for anybody who is starting their career without a college degree, make sure you’re really confident in who you are. We have a lot more conversations around community college or gaining technical skills. However, there’s still a little bit of a stigma. I would encourage you to feel confident that you bring something that other people don’t bring. The life experience that I brought to the White House — other people didn’t have that, and it’s valuable. Look at it like a trade-off and as if you’re bringing something unique that other people don’t have.
Her Agenda: There’s tons of advice about overcoming feelings of doubt, frustration, and inadequacy, but you, Deesha, said enough is enough! What did it feel like when you finally broke free, and how would you encourage other women to break free from these thoughts they may have?
Deesha Dyer: I love the framing of ‘breaking free’ because it’s honestly what it felt like. It’s almost like you don’t realize it until you do it. I used to laugh at people on Instagram who would be like, ‘I’m free,’ or ‘I’m soft life’ because it sounded a little weird and then it happened to me. I started to care less about people’s opinions and step into who I was. It sounds so strange to big yourself up and say, ‘I look good today’ or ‘I know I’m smart.’ In my day, it came off like you’re being conceited. Then you start to retract like, ‘so do you girl.’ So, for me what it felt like and what it still feels like because I’m still in the process is, I’m so excited because I discovered this before I got too old. I feel like a lot of Black women don’t do that. So, the advice I offer is to really go back and dig up the root of when you first started feeling this way and reflect on where you’re at now despite all of it. So let’s close that door, heal from that, and realize imposter syndrome is a scam to make us feel like we’re not worthy. And you can’t mantra and affirm yourself to death. You have to figure out the root, heal from it, and then say your affirmations so it really sticks.
Her Agenda: I love how you mentioned there’s a roadmap and you can’t skip to the part where you affirm and mantra yourself to death. Now that you’re more confident and sure of who you are, do you have any affirmations you tell yourself? Which ones work for you?
Deesha Dyer: I do. I’m a person of faith so one of my affirmations is ‘God is and always will be.’ This grounds me in the space that whatever happens, I’m going to be okay. The very basic ones like I am worthy, I am gifted – these are things that I tell myself too. Especially during this book process, it’s a lot. You will get a lot of no’s and negative reviews. Another one is I have something to say.
Her Agenda: Why now?
Deesha Dyer: I love this question. One of the reasons why I wrote the book now is because I’ve been seven years out of the White House. I finally understood the experience and what I went through. It was such an amazing experience and looking back, a lot of times, I was walking through a fog because I was thinking I had to prove myself. I had to reconcile with that, forgive myself, and show myself compassion, which took a while. I also think I didn’t feel like I had anything to write about. As imposter syndrome tells you, sometimes it is ‘Great! You have a story, but so does everybody else.’ Then I would go on speaking engagements, and people would ask me, ‘When is this book coming out?’ I spoke at Spelman, and the girls were crying, telling me that I made them feel seen. I had to affirm in myself that I have a gift and I need to give it to people. So now is the time.
Her Agenda: Writing a book is a brave and selfless act. Your words will live on after you and inspire generations to come. What do you want readers to receive while learning about your journey through your book?
Deesha Dyer: I want people to receive that they are this worthy jewel since the day they were born. I want people to walk away, realizing that they are not alone. One of the biggest things I hear from people is ‘I can’t believe you feel that way.’ Or ‘I can’t believe you would do that. You’re so confident.’ However, this book will tell you otherwise. Sometimes, comfort and healing can be found in community. I can’t be in community with everybody, so my book is my way of doing it. I hope people walk away realizing how much they’re loved and how much they’re valued for simply being themselves. I hope people walk away with the inspiration to start seeing themselves differently. I was very careful when I wrote my book because I didn’t want it to be prescriptive on exactly how to do this because I didn’t want to disappoint people when they did something and it didn’t work. I also respect that everyone is different. So, instead, I wrote a book about what worked for me and tidbits that will motivate someone to do what works for them. This is what I hope people walk away with, and some entertaining stories, of course!
Her Agenda: How did you create the title of your book, and what does undiplomatic mean to you?
Deesha Dyer: Well, my husband came up with it, so I have to give him a little bit of credit. Undiplomatic to me, is not a negative thing. It’s how I got here, and it’s who I am. I did not come through the diplomatic channels. I did not know what Washington, D.C., looked like. I did not know how to set a table. I didn’t know how to do all these things that are considered diplomatic for the role that I had. Even going back to the subtitle of my attitude, I was always told that I had an attitude and that I was too loud. I was like, you know what, this is just a label that I’m going to take and redefine. I’m going to say, ‘I am undiplomatic’ with power versus seeing it as a negative. Undiplomatic means to me that you’ve taken your gifts that are not like everybody else’s, and you’ve chosen to succeed with them. I am undiplomatic with pride.
Her Agenda: What was the book writing journey like?
Deesha Dyer: One of the highlights was spending time with myself by myself. It was really great recounting experiences and looking back at the journals that I wrote back then. That was a fun trip down memory lane. Submitting the book was even better. Overall, people receiving it as they read bits and while I spoke to them about it really means a lot. When you’re writing, sometimes you’re not sure if you’re communicating what you’re trying to say. When I would post snippets on Instagram, and people let me know it was dope and that they really felt what I was saying, it gave me confirmation like, okay, we’re getting somewhere.
Her Agenda: I love that your book highlights your self-discovery journey because, as women, we’re more than our careers. What’s been a highlight in your life as you’ve grown and developed into the woman you are today?
Deesha Dyer: I did get married a few years ago. I’m 46, and I got married when I was 44. Finding love in the way that I found it has been amazing. I found someone who reflects the same kind of love that I always wanted and the same kind of love that I always wanted to give. A lot of that came with me loving myself in a way where I didn’t compromise foundational things. Another highlight is discovering the art of play. I miss doing things like cooking for fun, sewing curtains, or going on a walk and picking fruit. I think a lot of times, Black women are from marginalized and historically oppressed communities, where our responsibilities start very young. We become responsible for how we look, how we dress, and a bunch of other things, and the play goes out the window. So, discovering the art of play has been a highlight.
[Editor’s note: This interview has been edited for length and clarity.]
