Issa Rae Gives Stephen Colbert Her Best Advice: 'Don't be Afraid to be a 'B***h'

With a Peabody Award and Emmy nomination under her belt, Insecure creator and star Issa Rae has learned a thing or two about more than just being a woman in Hollywood but how to survive as a boss in Hollywood too. So it’s not all that surprising that the director, writer and producer often gets approached by up-and-coming talent for advice.

While appearing on The Late Show, Rae said since Insecure premiered on HBO three years ago, people regularly ask her for advice. The 33-year-old said she’s always willing to offer whatever life tokens she can, which usually include the typical just “be yourself” line. She did admit sometimes she doesn’t “know what to tell them because everybody’s journey is different.”

The biggest slice of advice Rae could offer, though, came from a few of Hollywood’s leading women— Shonda Rhimes, Ava DuVernay, Mara Brock Akil and Debbie Allen—all of whom still advise her today. “Don’t be afraid to be a b***h,” Rae said. “And it’s so true.”

Rae told host Stephen Colbert as a young woman coming up in the industry, she constantly seeks advice from the incredible directors, screenwriters and producers that have come before her. “I tend to be afraid of upsetting people and that will get you nowhere here, especially when you’re like trying to create a show,” she explained.

“As a showrunner, being in the industry, just as a woman once you’re labeled difficult your career is kinda over ‘cause it’s like everybody’s saying, ‘Oh she’s hard to work with. Beware.’ And then you don’t get many chances to fail,” she continued.

The advice seems to fall in line with the theme of Insecure Season 3, which premieres on HBO on Sunday. Rae said many of the characters on the show will be adjusting to adulthood during the new season and trying to determine their next steps towards success.

“This season is about adulting. It’s about our characters learning how to know better and do better, ‘cause they’ve made a lot of mistakes. They’ve made a lot of poor decisions, which may or may not be based on decisions I’ve made with my friends,” she said. “But they get to a point where when you’re in your 20s people are like, ‘Oh she’s just in her 20s. You forgive her.’ But after a certain point, you have to do better.”

Join the Discussion