Key Takeaways
- Issa Rae shared that despite public perception, she doesn’t currently feel successful.
- She discussed her fear of financial instability and how quickly things can change.
- Rae also recalled using all her savings to self-fund a pilot early in her career.
Issa Rae opened up like never before during the premiere of “Not My Best Moment,” iHeartPodcasts and Unanimous Media’s new weekly interview series hosted by KevOnStage. Rae peeled back the curtain on what fame really feels like behind the scenes.
The Emmy-nominated actress, writer, and producer admitted that despite outward appearances, she doesn’t consider herself successful right now. “I know that I appear successful to other people, but right now, no, I feel really stagnant… Because I only feel successful when my s**t is on the air. I don’t have s**t on the air right now,” she told the comedian.
Rae also spoke candidly about a lingering “what if” that keeps her up at night: Although she acknowledges that she is currently “rich,” that status is fragile. “I say that I’m rich right now, and that is great, but that’s a very current thing,” she explains. “I think about that constantly. I know that I can save now, and that was my issue before, it was just really hard to save money. But yes, this can all go away immediately and it could go away for some shit that we were just talking about because a clip surfaces, or people decide they don’t f**k with you anymore, and I pride myself on being able to create on a dime… Things change when nobody wants to watch you. And I’m still at the mercy of that.”
Issa Rae on betting on herself early in her career
Elsewhere in the conversation, the “Insecure” creator reflected on one of her biggest financial mistakes — overspending on an independent pilot before her major break. “It was the stupidest thing I've ever done because it was literally all the money I'd ever made in my life until that point,” she revealed. “My business manager had called me while we were in the middle of the first pilot and was just like, ‘Sis, what did you do? What are you doing?’” The 40-year-old continued, “We were in pre-production, we had hired these directors, we had cast, everybody was hyped to be doing it. I couldn't be like, ‘Psych, I don't have the money to do this.’ So I just had to figure it out and I didn’t know what to do. He was helpful and was just like, ‘We’ll figure this out, but no more eating out.’ And I did. It was bad.”
That leap of faith, even with the missteps, ended up shaping Rae’s creative confidence that would later define her career.