There are so many reasons creatives should look up to Issa Rae. She constructs amazing stories and characters, is unapologetically herself and is a real-life example that if you work hard enough, you can truly have it all. But, one of my personal favorite things about the mogul is the way she constantly creates opportunities for others. In a recent interview with CBS This Morning, the actor, producer, and entrepreneur sat down with Gayle King and had a full-circle moment where she opened up about the final season of Insecure and why it's only the beginning.
This is not the first time we've seen Rae and King together. In 2016, when Issa Rae was most known for the still-hilarious and popular web series Awkward Black Girl, she shared her feelings on what it's like to truly live the title with King. "It's [awkwardness] just within me, it will never go anywhere. Like, I've always related to just feeling uncomfortable and out of place." Now, five years later, she admits that while that feeling is still there, she has changed a bit since the 2016 interview.
She tells King, "I feel more confident that I belong here. In Hollywood as a storyteller there's a sense of like, 'I know what I'm doing.'"
Well, I think it's safe to say we definitely agree with her because Issa has racked up so many wins. And Gayle King made a point to list a few of them aloud, like, a plethora of magazine covers, starring and producing in multiple films, securing the bag with an eight-figure exclusive Warner Media deal, and marrying her bae in a secret wedding! But through it all, Issa feels her and the cast's true mission is to create opportunities for others. And when making Insecure, she was intentional about doing just that.
At the start of the series Issa wasn't sure it would be successful but wanted to make sure that regardless, it was helpful to the cast and crew. "At least the people who worked on our show would've had experience. Which is like, the excuse that Hollywood always gives for why they don't hire people of color, and Black people specifically." She continues, "At least they could say 'we worked on one season of an HBO show,' and hopefully get another job, but we were fortunate enough to get five seasons, and watch people grow."
King also made a point to note that Insecure gave many of the actors, staff, and crew their first opportunity at a show on this level, to which she inquired if Issa marvels at that at all. Rae responded beautifully, saying:
"We changed each other's lives. So in that way, I'm just appreciative to have grown with them, to be in the trenches with them, and we have so many memories. We all have the mission to open the door and keep the door open–to make sure that we create a pipeline."
Jeff Kravitz/FilmMagic for HBO
It's encouraging and inspiring to see a Black woman who truly understands our stories and is telling them in such an authentic and engaging way, and it's why so many of us root for her, the same way she's "rooting for everybody Black." When asked how she feels about setting examples for creatives, she replied, "It means everything, because I know what it meant for me to watch those shows from the '90s and aspire to that and think like, 'Oh this is possible for me to do.' And these are stories that people care about, matter, and shape me. So to be able to do that for another generation, I'm extremely proud of that."
I'll be honest, I'm really going to miss Insecure Sundays, but it's encouraging to know that Issa has so much more in the works.
"I still feel like a beginner in many ways. I have so much more to do," she says firmly.
Featured image by Emma McIntyre/WireImage
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Skylar sees things differently. At the time, she was shooting content on her iPhone. Temi came into the picture with a new perspective, an understanding of tech, and, eventually, a camera. “He doesn't give himself enough credit,” Skylar says. “He wasn't just my tripod. He wasn't just standing behind the camera and going ‘click.’ He was giving advice. He was giving me insight to how I could look at things from a different perspective. And I was like, 'Oh, he’s an artist.' I think it was maybe a heartbeat of that kind of energy of like, ‘Baby, can you take this picture?’ And it turned so quickly into, we're partners. We can work together in a way where we're advancing each other's creative thinking.”
The pair often says they’re two sides of the same coin. Skylar is an Aquarius. She attended art school, paints, and loves poetry. She’s more than happy to let the couple’s management firm and agency, Kensington Grey, handle their admin work. And, she loves to sleep in. Temi, on the other hand, wakes up early. He’s a Virgo. He loves a to-do list and regularly checks in on the couple’s brand partnerships spreadsheet to make sure everything is on track.
Because his storytelling was steeped in his love of technology, he didn’t always think of himself as a creative person. “Where I [am] the dreamer who wants to pluck things out of the sky and spend all day with my head in the clouds, Temi [is] so good at grounding me and helping me figure out how to make things make sense on paper. We just work together in such a complimentary way,” Skylar says.
It’s been more than six years since Brooklyn-based couple Temi and Skylar started dating, and nearly four since they cemented their working relationship. On TikTok and Instagram, the couple’s travel, fashion, and home content regularly rack up hundreds of thousands of views. They’ve worked with brands such as Coach, Aesop, Away, and Liquid IV, bringing their vibrant perspectives to every campaign they execute. Still, nearly two years since both Temi and Skylar committed to full-time content creation and creative directing, the couple says their romantic connection remains their priority.
“We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting,” Skylar says.
Working from home can make it hard to separate work from personal life for any entrepreneur. It can be even more challenging when your business partner is also your lover. Temi and Skylar had already used couples therapy as a tool to help them effectively communicate with one another. When they ran into challenges while working together, their therapist helped them set physical boundaries to help combat the issues.
"We told each other we would much rather go back to full-time jobs and preserve our relationship than to be full-time freelancers, barely getting a night's rest [and] barely kissing each other because we're so busy shooting."
“It actually took us doing very specific physical things to create boundaries between work and play in our relationship,” Skylar says. “So, for instance, we will only have conversations about work when we're out of bed or we're at the table or in the office. Initially, when we started, we had to light a candle to say that, 'Okay, this is a space where we're connecting, we’re not talking about work.' We needed really hard boundaries at the top. And then it became a little bit more organic.”
The boundaries have been crucial to implement, especially because the couple began working together so naturally. When the pair first met, Skylar was NY-based a social strategist for BuzzFeed and was using content creation to drive business to her lingerie company. She was shooting her own content. Temi was working for Microsoft in D.C. He’d recently traded in his DJing equipment for a camera. “I've always loved taking pictures,” he says. “Even when I was a kid, my African mother would wake me up at 3:00 a.m. [during a] party, and be like, 'Come take the family picture.'”
Growing up, Temi says he watched his parents support each other and be the true definition of partners. He knew he wanted the same for his own relationship. But, the couple also wanted to make sure they were being financially responsible. The pair didn’t quit their traditional jobs until they’d saved up two years' worth of their cost of living. And, Temi received his Master of Business Administration from New York University with the knowledge that it could either help him advance in his corporate career or be applicable to his business with Skylar.
Temi and SkylarCj Hart @hartbreakToday, they say their working relationship is more of a “quiet dance.” They still implement some of the boundaries they learned in therapy, but they also lean into their natural strengths and deep love for one another. When we speak, Temi has planned a date for the couple to see Princess Mononoke in 4K IMAX and added it to their Notion so they can factor it into their busy schedules. “I fully plan to date for the rest of my life,” he says.
Skylar says the couple doesn’t just wait for date nights to check in with one another, though. This often happens in the mornings, after Temi has made her peppermint tea and poured himself a cup of coffee. When they ask each other how they slept, she says, it’s not just a “nicety.” It’s a genuine question meant to foster connection.
“A lot of it happens during the day in the midst of work. We'll stop and we'll hug. Or we’ll slow dance in the kitchen,” she says. “Sometimes it's hard to set a whole date night when you have 7,000 things going on. So, we must grasp these moments and check in when we can. And I think it's become so organic to us that I actually didn't even realize how often we do it. But all day long, we're like, 'Are you good? I felt like your energy shifted,' because we're best friends, we just know. We just feel it happen.”
What’s better than being in love? Building wealth while doing it. Watch Making Cents here for real stories of couples who make money moves together.
Featured image by Cj Hart @hartbreak