Issa Rae Wanted to Be a Bartender, But She Became a Business Mogul Instead

In ELLE.com’s series Office Hours, we ask people in powerful positions to take us through their first jobs, worst jobs, and everything in between. This month, we spoke to producer, Insecure creator, and serial entrepreneur Issa Rae. The multi-hyphenate became a beauty investor in 2020, when she joined clean hair care brand Sienna Naturals as co-owner, but by then, she’d already spent years acting as a “guinea pig” for Hannah Diop, Sienna Naturals’s co-founder and Rae’s sister-in-law. “Back in 2013, I had just done the big chop a couple years earlier,” Rae says. “I cut it, because it had seven different textures and heat damage, and I never properly took the time to take care of my hair. Her products came along at a time when I was learning how to do that.” Now, five years after officially teaming up, Rae and Diop’s brand is finally available at select Sephora stores nationwide. To mark the occasion, Rae tells us why being in-store is so important for beauty brands, her best advice for aspiring creatives, and why she hates the phrase “stay in your lane.”

My first job

My very first job was babysitting cats for the lady next door, and that’s how I discovered that I was allergic to cats.

My worst job

My worst job was working in a slave ship at a museum for a year when I was 24 years old. Emotionally, it was so hard, and to literally be on a slave ship was just soul-crushing.

My favorite job

Besides the job I have now? I loved waitressing. I actually loved serving, and I loved being in a restaurant. My ideal job was working my way up to being a bartender. So whenever my friends throw parties, I am the bartender, and I always get compliments on my drinks. I’ve perfected the espresso martini. I can do it with tequila, I can do a really good one with whiskey, but vodka is my specialty.

Design Courtesy of Leah Romero; Photo by Tyren Redd

Why it means so much to bring Sienna Naturals to Sephora

It’s incredible. Sephora, specifically, is so great with new brands and amplifying them. They’re able to help business owners maximize their potential. They’ve been a real champion for our brand’s success, even just through their incubator program. But to be in the physical stores is so great for discovery. It’s hard to stand out in a crowded marketplace. Casual Sephora browsers, like myself, might be hesitant to buy something online—but when I’m in the store, I’m like, “Okay, I’m here. Let me just try it out.” To be able to have that opportunity is everything that we could ask for.

My everyday hair care routine

I probably wash my hair every two days with the H.A.P.I. Shampoo and the Untangled Conditioner, which I love because my fingers just slide through my hair. On a regular day, I’ll apply the Dew Magic Leave-In Conditioner immediately after. I’ll add the Dream Curl Mousse on top. And then I’ll put my hair up into a bun and do my edge control, which is not Sienna Naturals. Sienna has not made an edge control yet, and hopefully they will get there. I’ll just lay my hair down, and then I’ll wrap it so that it’s slick, and then, boom, go to work.

On being involved in multiple industries

I like a lot of different things, and I’ve never wanted to feel limited. The phrase “stay in your lane” has always triggered me, because what if I like switching from time to time? What if I get restless in one space? I want to know what I can do, and I want to know what I can add value to, and it’s fun. And when it’s not, then I won’t do it. If I don’t feel like I can contribute to a particular business, and it doesn’t make sense, then I also won’t do it. It’s really about diversifying my interests and portfolio.

Design Courtesy of Leah Romero; Photo by Tyren Redd

How I juggle all of my projects

I work with a lot of different capable people that help me balance things, so I’m not running every business myself. But I’m great about regimenting and taking the time off when I need to focus on a creative project. Just this last week, I was like, “Okay, I’m not taking meetings. I have to finish writing this second draft of this project, so unless it’s absolutely important, from Wednesday to Monday, I’m not talking to y’all and focusing.” Now, that’s over, and I’m back to back-to-back meetings all this week. People are great about respecting that time for the most part.

The worst career advice I’ve ever received

When I was first conjuring up the idea for my web series, The Misadventures of Awkward Black Girl, I broke my own cardinal rule about not sharing my ideas until I’ve already done the work to complete them. A colleague was pressing me about what I was working on, and I told him about my series idea. He said it sounded dope, but that I should take “Black” out the title. He said, “You don’t want to exclude anybody or turn them off from watching.” It was coming from a good place, but I ultimately determined that anyone who was turned off by “Black” in the title wasn’t meant to be my audience in the first place.

My best advice for aspiring creatives

Find great people your age to work with. And find people who are passionate to hold you accountable for what you say you want to do. That was essential for me. I met a girl in college, and I told her I wanted to be a writer, and she was like, “Oh, cool. Let me read your script.” I was like, “Oh shit—I don’t have one. I just want to be a writer.” And she was like, “Well, let’s write one together.” And that changed my life, because I finally had a real piece of material. I had written things in the past, and even started scripts, but never fully finished or revisited them. Finding someone who challenges you to be who you say you want to be is essential.

The dream job I haven’t done yet

Man, I want to go on tour as a musician so badly. It looks so fun. Artists go around on a sick-ass tour bus or a decked-out private jet and perform for thousands of people who, in most cases, know their songs word for word? And sometimes, when you get lazy, you can just point the mic to the audience, and they’ll do the work for you? Also, the choreography that probably fulfills anyone’s daily cardio goals? If only I had musical talents.

When I first felt like I belonged in Hollywood

The first time I ever went to the Golden Globes. I felt like I was in the company of so many people I admired, and I felt like I belonged there. Up until that point, so many other red carpet appearances felt like, I just barely made it here, I don’t know what I’m doing. But that felt like, The first season of my show [Insecure] is on the air, and I’m in this space, and maybe I’m supposed to be here.