A part of the path to success is charted in having the vision, stamina, and enthusiasm to complete certain goals that lead to your ultimate destination. But once you get there, then what?
In many people's eyes, Issa Rae has reached an enviable level of success. From initially showing interest in the theater when she was in high school and starting her own YouTube series, Awkward Black Girl, to what many people now know her for, Insecure, Rae has achieved an unconventional level of success. Recently, Rae sat down with Glamour for their cover story to talk about charting her own path to happiness, why she was initially embarrassed that she was a YouTuber, and why complacency will never be on her radar.
The level of fandom and Twitter chatter Insecure has garnered is yet another example of why so many people are interested in "our" stories. The 33-year-old was able to recognize an unfulfilled niche in the entertainment market and blazed a new trail for other creatives to follow. However, Rae says she didn't exactly have anyone to look up to when she was starting out on her journey.
"There was no blueprint to do this. There was no one I could look to to be like, 'Oh, so-and-so made some videos and then had a television show, and then did movies...You kind of just do it."
Now in its third season, many of us couldn't imagine our lives before Insecure. We love it because we feel seen and it gives us so much life. Being the creator, star, and writer of her own television show might make some imagine that Rae is in cruise control when it comes to her career. But for Rae, she says that complacency is something that she never wants for herself and that she is on a quest to get better, keep learning, and continue to top the last thing she did. She told Glamour:
"I am always striving to get better. I am always thinking, 'OK, how can I top this? Or, how can I learn from this?' I just never want to be complacent."
One of the greatest feelings is doing what you love. Unfortunately, for many people, the option of doing that takes a backseat to paying the bills and putting food on the table. Rae recognizes that she is fortunate enough to have created success doing exactly what she loves, but also acknowledges that every breakthrough isn't easy, and proves that even creative geniuses have bad days. Issa said that she maintains good vibes despite life's bumps in the road by focusing on the silver lining.
"I'm doing what I love, and that is never lost on me. Even when I'm in my most frustrated moments, I'm like, 'There's always a silver lining.'"
Rae has blazed new trails in television during a time where representation is so needed. And now she will be charting a new path in film as well with the upcoming movie The Hate U Give, set to premiere in October.
Rae is an example of why following your passion is the ultimate win. She is proof that you determine your own success when you are able to remove yourself from complacency. Just remember to learn, grow, and keep trying.
To read the rest of the interview with Glamour, click here.
Featured image by Jerod Harris/Getty Images
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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
