‘Clearing A Path’: Luminary Honoree Issa Rae Drips In Authenticity and Purpose at The Women of Power Summit


She doesn’t step. She doesn’t walk. She just floats. Can’t nothing bring down the real Issa Rae.

Our latest luminary honoree graced the ballroom stage at the Bellagio Convention Center for a conversation that counts with BLACK ENTERPRISE’s VP/Deputy Chief Content Officer Alisa Gumbs. 

Black Enterprise’s Alisa Gumbs and Issa Rae in a conversation “Doing It My Way” at the Women of Power Summit (Image: Black Enterprise)

“There’s such positivity in power, especially when it’s in groups and especially when it’s very well-intentioned. It is about making sure whatever power that we yield is always well-intentioned… and with the right people,” Rae said.

It was a Black girl moment as the ladies’ stunning entrance cued Janelle Monae‘s Float, prompting Issa Rae to shout “my song” and the audience to embrace her authentic response.

“Cheers!,” Issa Rae exclaimed holding a glass of red wine.

Sponsored by United Health Group, the segment “Doing It Your Way” followed the illustrious second annual Luminary Awards and luncheon. Rae, an award-winning actress, writer, producer, and comedian, was honored among our sisters fighting the good fight, creating new paths, and lighting the way for us all.

While Gumbs acknowledged Rae”s overflowing résumé, the room couldn’t resist Rae’s punchlines and jokes.

“It’s not always as easy as it sounds to show up as your authentic self or to bring your full self to work,” said Gumbs as she opened up the stage to ask Rae about tapping into her authenticity.

“There’s a version of me that you present outwardly and then I just want to be at home chilling and not interact,” Rae said.


“Generally I don’t think I can do my job if I’m not authentic to myself. Like being a writer, a storyteller. even in creating businesses I’m always thinking about the most real version of myself,” she added.

Bringing laughter and empowerment to a room of 1,800 Black professional women, Rae broke down her testimony about how she is succeeding on her own terms — “creating authentically while intentionally celebrating the purpose.”

“If I was a false version of myself, or otherwise, it wouldn’t work,” Rae said.

Corporate professional turned creator

Starting in the corporate world, Rae was able to leverage her unique skillset to succeed at her job, but she had other dreams. Corporate just wasn’t for her.

“I didn’t quite fit in,” Rae said. “My corporate experiences actually inspired The Misadventures of Awkward Black Girl. So that was the best part of it.”

The New York Times best-seller, The Misadventures of Awkward Black Girl, was based on Issa’s third scripted web series and the first one she starred in herself.

She continued: “I’m glad I had the experience because it spawned my creativity and made me hungrier to leave this space.”

Although Rae may have jokingly found the title “serial entrepreneur” insulting, there is no denying her powerful presence as a creator and owner in the eatery, hair, and television industries. But she acknowledged her ongoing journey of navigating time management and longing to be around the people she cares about.

On her own terms: The gate is open

With business dreams from an early age, Rae aims to “have a company and several companies that consider us first and not as a stepping stone.”

“There is something about building businesses from the ground up that is so satisfying to me,” Rae said.

According to Rae, breaking out into the television industry is hard. The Rap Sh!t creator is no stranger to the wrath of gatekeepers who told her no. She recalled how disheartening it was getting a lot of pushback in her earlier days, especially as a creator who proudly repped her Black roots. But the craving for that nostalgic feeling of Black love stories inspired her to create.

“I never knew If I could, that I could be successful at that.”


She continued: “Because we’ve always seen that we’re kind of a flash in the pan.”

“This would be my ticket,” she recalled about her previous online creations, “and that didn’t happen” until she started playing by her own rules and building on online following.

“The journey to be fearless and in the pursuit of what I wanted to was absolutely terrifying because in my mind if I take this leap, I don’t why it seemed like a public leap. But it can also be a very public leap.”

She added: “It doesn’t feel like anything to be a trailblazer,” Rae said. In so many ways, I am still having to clear a path and prove myself all over again. And I am willing to do that. But you can’t take that position for granted at all.”

(Image Black Enterprise)


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