Issa Rae Shares Her No-Nonsense Playbook for Winning — ‘Don’t Be Afraid To Be A B—ch’ - Page 3
Play the long game. Consistency builds longevity.
With a growing fanbase and undeniable buzz around her name, Rae eventually caught the attention of Hollywood heavyweights. In 2012, after her viral success on YouTube, Rae met with Casey Bloys, Chief Content Officer for HBO and HBO Max. According to CNN, that meeting marked a turning point. HBO saw her potential and offered her the opportunity to bring her creative vision to the network.
Teaming up with executive producer Prentice Penny, Rae went on to co-create Insecure, the critically acclaimed series that debuted in October 2016 and ran for five powerful seasons until 2021. The show followed best friends Issa and Molly as they navigated love, friendship, career challenges, and the sometimes messy, always relatable reality of adulting. What set Insecure apart was its authenticity. It wasn’t just entertaining; it was honest, vulnerable, and deeply reflective of the Black millennial experience.
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Each season raised the bar. Rae and Penny never let up, consistently evolving the storyline and deepening the complexities of the show’s characters. Issa and Molly’s relationship—full of loyalty, tension, growth, and love—resonated with audiences in a way that felt personal. The show also stood out for its cinematic visuals, curated soundtracks, and cultural nuance—and its impact was undeniable.
Insecure earned four Emmy nominations and won a 2018 Peabody Award for excellence in entertainment.
Despite her growing influence, Rae has been candid about the challenges of breaking new ground in the industry. Per CNBC, speaking at the 2022 FutureWorks conference, she admitted that as Insecure gained momentum, she was initially “scared” of being seen as “difficult” when pushing for creative risks. That fear of rocking the boat is something many women—especially Black women—face in professional spaces. But Rae turned to a powerful circle of mentors, including Shonda Rhimes, Ava DuVernay, Debbie Allen, and Mara Brock Akil. Their advice was clear: “Don’t be afraid to be a bitch.” In other words, speak up, take risks, and own your power.
