Even Issa Rae, the creator behind “Insecure” and a creator-turned-power player in Hollywood, recently said she doesn’t currently feel very successful. 

Rae said even big wins can feel small, and right now, she doesn’t feel very successful. She told host Kevin Fredericks, aka KevOnStage, on his new podcast, “Not My Best Moment” that despite outward markers of success, she’s feeling “stagnant” because her primary joy — having something new on the air — isn’t happening at the moment.

“I know that I appear successful to other people, but right now, no, I feel really stagnant,” Rae said, adding a blunt assessment of how tied her sense of achievement is to active projects. “I only feel successful when my sh*t is on the air. I don't have sh*t on the air right now.” 

Rae also walked listeners through the grind that got her here —  from self-funding indie pilots to navigating network development notes — and the emotional toll of betting on projects that don't land. She admitted she once financed multiple pilots herself, saying she “accidentally” paid for them and that they were roughly “$50,000 pilots each,” a gamble that taught her hard lessons about spending and ownership.

Beyond money, Rae confessed to a persistent fear that her visibility could vanish. When Kev asked if she ever worries “what if this all goes away?” she answered plainly, “Every day.” Her admitted anxiety reveals a creator’s paradox: outsized accomplishment on paper, fragile momentum in practice. 

For Kev, Rae and anyone listening, the takeaway is both sobering and familiar. Even those who’ve “made it” can feel perpetually mid-climb, driven by a hunger that only new creative work seems to satisfy. 

What is success to you?