The multi-talented Issa Rae is a bonafide Hollywood powerhouse, but her road to success was not one she paved alone. “I tell young people [just starting out in their careers] to search for other young people who are just as hungry as they are and collaborate with one another,” says Rae. “I think there's such a power in working with the people next to you and building together.” 

Her latest project is all about lifting young creatives up. Rae has partnered with delivery service Shipt to promote its new, discounted membership program for kids heading to university. Alongside Shipt’s CMO Alia Kemet, Rae also mentored four students from Howard University this summer as they worked to create a national advertising campaign for other college students.

When I meet the ever-stylish Rae (dressed in a fabulous fringe Khaite dress), she tells me that mentoring these Howard students was a no-brainer. “I come from a family of HBCU [graduates],” she explains. “My brothers went to an HBCU, and the Shipt leadership team went to HBCUs, so my support for [the schools comes] naturally. It was just an easy collaboration.”

Rae has plenty of career and business advice to share with young Black creatives, lessons learned over many years in the spotlight. “One piece of advice I've never forgotten from another woman is to not be afraid to be a bitch. That is such a worry of mine just even as a leader in how you come across, and that worry in the back of your mind can inhibit you from saying how you really feel,” she explains, potentially leading to more harm than good. Black women tend to face added challenges in business when it comes to standing up for themselves — especially when placed in mostly white and male writers’ rooms and negotiating tables. “Obviously, you don't have to be mean about certain things, but that fear of speaking your truth shouldn't prevent you from doing it.”  

One suggestion she wouldn’t make: Play by the rules. “[The worst piece of advice I’ve ever gotten is] ‘do it the traditional way.’ That means following the rules, waiting for someone to choose you, waiting to break in with other people's permission, and that just ... that didn't suit me, so I'm glad I didn't listen.” 

That rule-breaking ethos extends to how she dresses. “When people in fashion say certain things have ‘gone out of style?’ I think that's bullshit,” she says. “I think that if certain items of clothing define you or for a period of time seem to be out of season, wear it — that's you, and you can make it fashionable again. For me, nothing goes out of season. If you want to wear low-rise jeans till 2073, then that's your right. It'll probably be back by that time.”

Such life lessons have carried her far, but is there anything Rae would do differently if she went back in time? “I would do my twenties even dumber if I could,” she says with a laugh. “Be dumb in your twenties!” 

Shipt’s program is one of several projects keeping Rae busy during the ongoing SAG and WGA strikes. Her media company HOORAE — which includes a production arm, a radio station, and management for underrepresented talent — as well as her work running a hair care line called Sienna Naturals, are also filling that void. And, although she admits to being tired, her Capricorn nature results in a strong work ethic that keeps her creative juices flowing. 

“I love to work. My fear is being seen as lazy. My mom, she's always been like, ‘Just don't be lazy!’ My dad has been a hard worker all my life. … But I'm also a Capricorn at heart. Apparently, we love to work. At a young age, I used to want to keep myself busy—like giving myself homework when I was super young. I just love to build and do things.”

Adult Issa has no plans to stop what Young Issa started. When asked about her hopes for the future, Rae offers a powerful response: “I'm manifesting fair wages. I'm manifesting the industry to respect the people who make the industry possible. I'm ready to just launch so many projects when the time is right. I have so much more to say and so much more to do.”