As the Social Secretary to President Obama, Deesha is no stranger to VIPs and fancy parties, nor the doubt, pressure, and eventual confidence that comes with embracing such a prominent role while being true to herself.
In her newly released book, Undiplomatic, Deesha details her journey from a community school graduate with a passion for hip hop to serving in the coveted seat of Social Secretary at the White House. She recites stories from her book in a candid and powerful conversation with Michele Smith, a fellow trailblazing Black female executive. The two women, who have known each other since school days, shared their journeys, insights, and visions for the future. Their conversation was a blend of personal anecdotes, professional triumphs, and a profound commitment to community and cultural legacy.
Deesha began her early days as a hip-hop writer covering The Roots, or as she likes to say, before they were The Roots. Reflecting on her career path, she spoke candidly about imposter syndrome and the importance of authenticity. “I’m a good, lovable person…learning how to love myself out loud, that process is freedom and liberation.” she shared, emphasizing the need for self-love and continuous personal growth. Her experience at the White House was marked by a commitment to bringing community voices into the political arena, organizing significant events like Pope Francis’s visit, and infusing Black culture into the fabric of the White House. “I wanted to open the door and let people in,” she said. “I wanted to make the White House the people’s house. It was a magical time.”
Michele, who recently joined The Museum of Pop Culture as CEO, emphasized the transformative power of museums, describing them as platforms to celebrate cultures and untold stories. Michele recounted her involvement in strategy, operational planning, and activism over the course of a rich career, now focused on making museums accessible and community-oriented.
The conversation turned to the evolution of Juneteenth from a little-known holiday to a nationally recognized celebration of Black liberation. “Before George Floyd, Juneteenth was not celebrated widely,” Deesha noted. “Now, it’s woven into the fabric of the country, a day of liberation and recognition for those who fight for freedom, past and present.” Michele added, “Our museum was the first to recognize hip-hop as a genre. We opened our online portal of hip-hop artifacts to people all over the world.”
Both women shared their experiences with bias and the strategies they’ve used to overcome stereotypes. Deesha recounted her challenges at boarding school and in her career, where she often felt dismissed due to her lack of a college degree and her outspoken nature. “In school I was told I was bad, my attitude was bad,” she recalled. “But now, I know I am deserving and amazing, and I’m going to claim that.” She also highlighted the significance of bringing diverse voices into leadership roles and creating spaces for underrepresented communities. Michele likewise shared her commitment to continue self-improvement through coaching and learning, and her approach of always being prepared with multiple plans.
Looking ahead, Michele and Deesha are focused on creating lasting impacts in their fields. Under Michele’s leadership, The Museum of Pop Culture is preparing to celebrate its 25th anniversary, extending its mission to showcase the power of popular culture in changing public discourse. Deesha, through her public service and advocacy, aims to bridge the gap between education and pop culture, using her experience and platform to engage and educate younger generations.
In sharing their stories, Michele and Deesha offered powerful examples of resilience, leadership, and the enduring impact of cultural advocacy. Their conversation concluded with a call for women to uplift each other and work together to create inclusive and supportive environments. “We are in community today,” both women celebrated. Michele added, “We must uplift each other as women. It’s time to elevate, talk, and connect.”
