Issa Rae is still drawing on advice she attributes to Maya Angelou, a guiding principle that continues to shape how she moves through Hollywood and beyond. Speaking at the Create Canva Building Creative Empires for Social Good event at SoFi Stadium in Los Angeles, Rae joined a broader conversation about leadership and creative decision-making.
When asked about advice she wished she had understood earlier, Rae pointed to Angelou’s reminder that people often reveal their true nature early. She described how that idea has stayed with her through years of navigating partnerships, contracts, and creative collaborations.
For Rae, the lesson has become less about reacting in hindsight and more about recognizing patterns as they emerge.
Intuition and trust in creative decisions
A central theme in Rae’s reflection is intuition, which she described as an internal signal that often appears before logic catches up. She explained that she has experienced moments in both professional and creative settings where something felt off early on, even when she chose to overlook it.
Rather than dismissing those reactions, she now sees them as meaningful indicators. Rae noted that she has sometimes extended trust longer than necessary in business situations, even when her instincts suggested caution. Over time, she has begun placing more weight on those early impressions.
The shift reflects a broader change in how she evaluates relationships in the entertainment industry. Instead of relying solely on reassurance or repetition, she has learned to take initial discomfort seriously and use it as part of her decision-making process.
Insecure and the power of creative legacy
Rae also reflected on her work with Insecure, the HBO series that ran from 2016 to 2021 and became a defining project in her career. She views the show as one of her most meaningful accomplishments, particularly for its role in expanding opportunities for writers, producers, and performers.
The series earned her multiple Emmy nominations and helped reshape conversations around representation in television. Beyond awards recognition, Rae emphasized its lasting influence on the creative paths it helped open for others.
She described the project as a foundation that continues to influence how she approaches new work, especially when it comes to building spaces for emerging voices in entertainment.
Film work and shifting industry expectations
Rae also discussed her more recent work in film, including producing the studio comedy One of Them Days, starring Keke Palmer and SZA. She noted the pressure surrounding the project, particularly given the limited number of studio comedies being produced and the heightened scrutiny placed on films led by Black women.
Despite that environment, the film reached a significant commercial milestone in theaters, reinforcing her commitment to continuing work in the genre. Rae framed the experience as part of a larger effort to support the return of studio comedies while expanding representation on screen.
She also pointed to the importance of collaboration with writers and creators she trusts, emphasizing that each project adds to a growing body of work aimed at broadening what is possible in mainstream entertainment.
A career shaped by instinct and experience
Rae’s reflections highlight a consistent thread running through her career: the growing trust in her own instincts. While Angelou’s advice remains a foundation, Rae’s interpretation has evolved into a practical approach to both creative and business decisions.
Her perspective underscores a shift from extended second-guessing to early recognition of signals that matter. In an industry where timing and collaboration can define outcomes, she has learned to treat intuition not as uncertainty, but as information.