Issa Rae Said She Doesn’t Always Feel Successful

NEW YORK, NEW YORK – SEPTEMBER 02: Issa Rae attends the US Open Tennis Championship at the USTA Billie Jean King National Tennis Center on September 02, 2025 in New York City. (Photo by John Nacion/Getty Images) (Photo by John Nacion/Getty Images)

Issa Rae had revealed that she doesn’t always feel successful in her career.

On the premiere episode of the new podcast “Not My Best Moment with KevOnStage,” Rae reveals she feels “stagnant.”

“I know that I appear successful to other people, but right now, no, I feel really stagnant,” Rae said.

Rae says she only feels successful “when my sh— is on the air.”

“Like, I can have the 18 businesses,” Rae said. “And those are, like, great passion projects, but like, what I do and what I get excited about isn’t happening right now.”

Rae also spoke about how her financial status is not always indicative of success.

“I say that I’m rich right now, and that is great. But that’s a very current thing,” she explains. “And I think about that constantly,” Rae explained. “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. It could go away for some sh*t 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,” she continued.

Rae then went on to share one of the biggest financial mishaps when she overspent on an independent project.

“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 called me while we were in the middle of the first pilot. ‘Sis, what did you do? What are you doing?’” “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.”