Issa Rae opened the first episode of KevOnStage's Not My Best Moment with a revelation most fans wouldn’t expect from her: she doesn’t feel 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 sht is on the air,” she said. “I don’t have sh*t on the air right now.”
That admission set the stage for a conversation about the pressure, risk, and self-doubt that have followed her throughout her career—even in moments when the outside world assumed she was winning.
Rae told KevOnStage (real name: Kevin Fredericks) that her fear of everything disappearing never fully goes away, no matter how far she’s come. “Yes, this can all go away immediately,” she said, explaining that fame can change overnight “because a clip surfaces, or people decide they don’t f*ck with you anymore.”
Rae reflected on the early days before Insecure, including a moment when she invested every cent she had into an independent pilot. “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 said.
Production had already begun—directors hired, cast assembled, momentum building—leaving no room for her to back out. Her business manager called in a panic, asking, “SIS, what did you do? What are you doing?” His solution was blunt: “No more eating out.” Rae admitted, “It was bad.”
The rise of her career also pushed her to clean up her online footprint. As soon as her pilot was picked up, she started deleting old tweets in massive batches. “I got that little program and started deleting in the writer’s room every day, 10,000 tweets,” she said.
She didn’t want past commentary—especially things she said during award shows—causing issues with people she’d later meet. “I was like, I don’t want no smoke.”
Rae also revisited her experience developing I Hate L.A. Dudes, a moment that made her question her instincts. “I forgot that they wanted to work with me because I’m me,” she said.
Surrounded by people who had longstanding TV experience, she found herself deferring instead of speaking up. “Surely I don’t have the right to express, ‘I think this is dumb.’” The project ultimately taught her to trust her voice again. “They want me to be as loud as possible with what I want to say.”