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Issa Rae looks back on making it big–and making big mistakes

The Emmy-nominated actor stars in a new Samsung ad highlighting her glow-up. What’s not shown, however, are all the lessons she’s learned the hard way.

Issa Rae looks back on making it big–and making big mistakes

The tagline for season three of Insecure couldn’t be any more applicable to creator Issa Rae’s career: “Glowing up ain’t easy”–she just makes it look that way.

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Rae’s seven-year journey from her YouTube series to a Peabody Award winning HBO show is spotlighted in her new Samsung Galaxy ad, “Made It.” As charmed as Rae’s life may seem in the spot–from watching her first episode of Awkward Black Girl go viral to calling the shots on set–she readily admits that underneath each milestone is a foundation of struggles and mistakes. Even with a hit show that was recently renewed for a fourth season, Rae is still trying to figure it all out.

“There are so many aspects you don’t think about. You’re essentially an entrepreneur,” says Rae of transitioning from YouTube to writing and executive producing a cable show. “That was the biggest learning curve of ‘oh, shit–I have to basically run a company.’ And running a company is something I still struggle with now.”

Part of that struggle for Rae has been learning how to be an effective leader. Having gone from a bootstrapped web series to a fully fledged writer’s room has been a necessary lesson in trusting the collaboration process and not keeping anything too close to the chest.

Insecure is my brain child, but I work with a showrunner, Prentice Penny, and he’s very much my partner. He’s also been very great about putting his ego aside, and I’ve had to do the same,” Rae says. “For me, it’s sometimes an instinctive ‘no’ when I hear an idea that I don’t think may work–that’s how I started out initially. But hearing out ‘bad ideas’ in so many cases led to great ones.”

Immediate communication has also played an integral role in Rae’s leadership style–that is to say, addressing issues or concerns before they have time to fester into something worse.

“It’s always come back to bite me. When you’re like, ‘I wonder if this moment affected our relationship? Well, let me just wait and see,’ as opposed to just checking in the moment, like, ‘Hey, this felt weird, are we good?” Rae says. “If there is a problem, if there’s anything you see, address it.”

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What Rae has learned from working on Insecure is going directly into her upcoming projects Sweet Life, a coming-of-age tale of teens growing up in Windsor Hills (aka, the black Beverly Hills), and Him or Her, an exploration of a black man’s bisexual dating life–just don’t expect her to have any starring role in either show. “I never want to be in a show that I star in and create again,” she says. “It’s the workload, and also I don’t want to do stuff that I’ve already done. I’m like, ‘I know what this is now–so what’s next?'”

What’s essential to Rae is telling a wide array of stories within the black community. Even if it may not be her lived experience, Rae is adamant about using the platform she’s built to “empower other voices to tell those stories.”

“That’s the pressure I feel,” she says. “I don’t want to just be known as, ‘She always tells these heterosexual stories or these black American stories’–I want to have a diversity of black experiences to acknowledge and claim.”

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About the author

KC covers entertainment and pop culture for Fast Company. Previously, KC was part of the Emmy Award-winning team at "Good Morning America" where he was the social media producer.

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