Former White House social secretary details her ‘Undiplomatic’ way of overcoming imposter syndrome

She was in a role that demands tact and courtesy, but now Deesha Dyer is getting “Undiplomatic,” opening up about her unexpected ascent from community college student to Obama White House social secretary. 

In her just-released book, “Undiplomatic: How My Attitude Created the Best Kind of Trouble,” Dyer recounts a 2009 conversation with her cousin that’s indicative of just how unlikely she and her family viewed her scoring an internship at 1600 Pennsylvania Ave.

“I told her [about the internship], and she kind of looked at me funny in a sense of ‘Why are you just saying part of the name of the store, like just saying White House versus White House Black Market?'” Dyer’s cousin thought her family member had snagged a gig at the apparel chain, rather than the executive mansion.

“And I was just like, ‘No, the White House — like the actual [place] where President Obama works. It was just this disbelief that she had, but it was same disbelief that I had,” said Dyer, who was at that time a 31-year-old part-time community college student. 

After being moved by Obama becoming the first Black president and applying and landing the internship, Dyer worked her way up to White House social secretary, a senior position that made her responsible for spearheading all the events at the White House, dealing with everything from the guests lists, to foods and florals, to the entertainment. 

But as she climbed the professional ladder, Dyer said, she suffered from a sometimes-debilitating voice in her head telling her she wasn’t up to the job. 

“Imposter syndrome is really when you feel like you are fraud, where you feel like you’re not deserving, that you’re going to be found out,” she told ITK in an interview.

“So maybe you get a promotion, and it’s like, ‘Somebody’s going to find out that I’m not really qualified for this role, that I don’t know what I’m doing, that I’m not deserving of it,’” she said.

“You spend a lot of time thinking about how can I make sure I can cover myself so people don’t think I’m dumb?” Dyer, 46, recalled.

Despite the internal struggles, she put together some epic, star-studded gatherings at the White House. 

She remembered a time when she came to Aretha Franklin’s rescue amid a foot-related failure when the late “Respect” singer was at the Executive Mansion to receive the Medal of Freedom from Obama in 2018.

“She had on high heels, and her feet were hurting so bad,” Dyer said. 

In an attempt to make conversation, she pointed out to the Queen of Soul that she had walked over to the event in sneakers, before planning to change into her heels.

“I made a joke about it, like, ‘You want my shoes?’ And she was like, ‘Actually, yes,” Dyer exclaimed. 

“I didn’t think she was really gonna say yes. And I actually gave my shoes to Aretha Franklin and then ended up taking an Uber home because I was like, I’m not walking anywhere, I’m in these heels.”

“I never got those shoes back, but it’s OK,” Dyer quipped. 

But most tales from the White House parties with the Obamas, Dyer said, she’ll forever keep under wraps.

“I think that in writing this book, one of my biggest challenges was [is] it OK if I mention this? If I say this? I don’t want to betray anybody,” she said.

“What happened at the White House, happened at the White House,” Dyer maintained. “Some of these things weren’t my stories to tell — they were really the president and first lady’s stories to tell.”

Dyer said while she might miss the ability to call up just about any celebrity with an invitation to the White House, it’s still possible to throw events that leave everyone talking, even without the power of a presidential invite behind you.

“You make it a memorable event by, like, really catering to your guests, really being like, how can I make this so everybody feels welcomed in this space?” 

“You don’t want people going into any kind of party or space where they feel like they don’t know where to sit down, or there’s not enough food for them to eat or the music is not universal,” Dyer advised.

“Everything that I do, I make it like a house party.”

Dyer’s last day of work at the White House came on Donald Trump’s inauguration day in January 2017, which she likened to a funereal atmosphere. The meeting between the incoming first family and the Obamas, Dyer said, presented one of the most stressful moments of her time there when Melania Trump unexpectedly arrived holding a “very identifiable cyan blue Tiffany’s gift box in her hand.”

“Now, this may not seem like a big deal to most onlookers,” Dyer wrote in her book, “but it was a very big deal to me because I’d confirmed with the Trump advance team that there was not going to be a gift exchange between the couples.” 

“At this point, I’m freaking out,” Dyer recounted, saying “with practically the whole world watching,” the Obamas were in danger of becoming “brand ambassadors for Tiffany and Co.”

Crediting Obama with quick thinking, Dyer said the 44th president took the box from wife Michelle.

“I met him halfway and grabbed the box,” Dyer said, potentially minimizing a total gift protocol snafu.

When she first arrived at the White House, Dyer said, she “didn’t know how to be diplomatic,” hence the title of her book. 

But she today views being undiplomatic as a “gift” that ultimately helped her to overcome her imposter syndrome.

“It was an opportunity to do things differently and to bring in different people, non-traditional people,” Dyer, who now runs the social impact firm Hook and Fasten, said.

 It also propelled her to put her experiences on paper, saying that many young, Black women she works with talk about feelings of not feeling “deserving” or “worthy.” 

“As we go into a presidential election, I’m hoping that it inspires people, who have never been in politics before, to get involved in whatever way they can and not say, ‘I don’t fit the mold.'”