If nothing else, Issa Rae is certainly busy. The actress, writer, producer, and New York Times bestselling author has achieved astronomical success over the past decade, parlaying the success of her beloved YouTube series, The Misadventures of Awkward Black Girl, into a book and hit HBO series, Insecure. Now filming its fifth and final season, she recently joined the Television Academy’s Executive Committee, and the ink is still wet on a deal that she just signed to produce new projects for WarnerMedia under the umbrella of her own media label, Hoorae.
Amid all of this cause for celebration and what’s sure to be a packed schedule, Issa made time to sit down for a virtual chat with Chief Member and Warner Brothers Television Group Chairman Channing Dungey. Together, the two talked about creativity, leadership, and what’s on the horizon — while Chief members hopped on camera to ask questions, and excitedly workshopped a potential “Insecure: The Movie” in the Zoom chat.
“I’m happy to be able to close this chapter,” Issa said of the process of bringing Insecure to a close. “I am a bit in my head, because it's just, you know, I feel that pressure and you only get to end the show once, but beyond that, I'm really excited that we got to tell the complete story I believe in.” Telling that story the way she wants to, however, has always required her to wear several hats. Since her YouTube days, the entrepreneur has been known for not only appearing on screen but also being in the writer’s room as well. Discussing her ascent, she said, “It’s been a constant juggle of roles and a constant balance: Do I want to be a creator? Do I want to run a company? Do I want to be a businesswoman? Because you can't do all of those things.”
Issa is passionate about seeking out and promoting new talent, as well as delegating tasks in order to keep her empire running smoothly. But she pointed out that she still understands that her role as a leader requires her to set a tone and model the culture you want to see reflected back to you. “It sounds obvious, but things start at the top,” she said. “And I was like, ‘Oh shit, I'm the top.’ So I really have to make sure that, you know, I'm big on respecting everybody. It's so important for everybody to have a voice. But it's also important as a leader to be able to discern what filters through.”
Of course, being a leader requires doling out but also receiving feedback. Asked how she distinguishes between constructive and ego-driven feedback, Issa joked, “I'm a masochist. I like to hear everything that’s wrong.” Going on, she explained how she looks for actionable feedback within the most negative critiques. “This person once wrote a comment on YouTube telling me to die and that my sound sucks and that I should go to hell and never create work again. And I thought, oh, they told me my sound sucks. I can fix that. And I'm capable of doing that. I can recognize that that's something that needs to be fixed and all that other stuff is just noise."
As for what’s next, the newly minted member of the Television Academy’s Executive Committee is excited to be a part of the discussion about diversifying Hollywood. “I have a lot to say in terms of how we can level the playing field and how we can not make the Emmys feel like such an exclusive, archaic club,” she shared. Naturally, she’s also looking forward to contributing to that effort by elevating new ideas and scripts. “I have an entire Senegalese side that I haven’t been able to explore yet, a West African side,” she explained, among other ideas. “But if they're not things that I've personally experienced, then I'm making damn sure that there are people in the room who have.”
“I think about things every day and I'm just like, ‘These ideas come, but who's going to do them?’” Issa said, which led her to ask members to help her find her next hire: “So, Chief — Chief of Staff, if anybody has any recommendations, hit my line. You heard it here first, everyone.”
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