Issa Rae’s Best Career Advice: Don’t Be Afraid of Being Labeled a ‘Difficult’ Person to Work With

By Morgan Smith

Issa Rae has built the kind of entertainment career people dream of: co-creating, co-writing and starring in a hit HBO series; landing a multi-million dollar film and TV deal; and building her own media company.

But the 37-year-old actor, writer and producer says it almost never happened, due to early-career struggles with confidence and speaking up for what she wanted.

Even right before her TV show “Insecure” premiered in 2016, Rae was “scared of being seen as difficult” to work with, she said at the Indeed FutureWorks 2022 conference earlier this month.

The fear stemmed from seeing how female creatives were treated in Hollywood. Whenever Rae sought out women writers or women directors, she’d hear “feedback from men, and in some cases women, about why I should not work with them,” she explained on a recent episode of Meghan Markle’s podcast, “Archetypes.” “It often came down to them being ‘difficult’ … That word in particular was used often.”

In response, she sought guidance from other Black women she admired in the entertainment industry: Shonda Rhimes, Ava DuVernay, Debbie Allen and Mara Brock Akil.

Their advice? “Don’t be afraid to be a b—-.”

At the Indeed conference, Rae called it “the best career advice” she ever received.

“They really stressed to me that I could never have this opportunity again,” she said. “They were like, ‘You have this show with HBO, you’ve been wanting this the entire time, and you’re scared to say no or be a b-word? What if you never get this chance again?”

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Since then, Rae said she’s approached all of her projects with that mindset, and it’s fueled her ambition.

“I don’t care how settled I may feel in my career, I don’t care how much praise I get,” she said. “I approach every project thinking, ‘What if I never get to do this again?'”

She added: “I’ve never been stagnant, I’ve never been satisfied … that hunger just remains in me.”

According to the Mayo Clinic, being assertive at work can help boost your self-esteem, earn others’ respect and reduce stress, especially if you have a hard time turning down requests.

You can practice by maintaining an upright posture and direct eye contact when speaking with co-workers, using “I” statements to describe your thoughts and feelings, and practicing saying “no,” the Mayo Clinic recommends.

But there’s a fine and sometimes unfair line between assertive and aggressive, and the “angry Black woman” stereotype can mischaracterize a Black woman’s passion for aggression. That myth plagues both the workplace and Hollywood, Rae noted on Markle’s podcast.

The advice Rae received from her career idols helped, she added: “I take away the fear of being labeled as [difficult]. I shouldn’t have to fear that if I just want something to be great.”

Now, if a friend were to call her “particular,” she said she’d take it as a compliment.

“To me, that means I have a sense of what I want,” Rae said.


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