When Lena Waithe speaks, everyone in the room stops to listen. Words of wisdom pour from her lips like honey, and her lucky spectators lean in to catch every last drop. Tuesday night, just a few days after many of us gave thanks with our families, was no different. A diverse group of people packed into the Melody Ehsani store for the "M.E. Speaker Series" to hear gems from the Emmy award-winning writer and actress of Master of None, the director of HBO's Insecure Melina Matsoukas, and actor Michael Ealy, who made a surprise guest appearance.
A steady chorus of "mmm's" echoed throughout the room as notable moderator Erica Williams Simon successfully steered the conversation around topics such as the measure of success and having seats at tables we previously weren't even allowed in the room to witness. It was clear that this wasn't just a panel discussion only worthy of a quick "I was there" snap or Instastory post, but a place of communion, where we could gather together, speak our truth, and more importantly, hear solutions from those who are winning on how to continue to make an impact as we go about our respective paths.
But what are words if only confined in one room? While the discussion was phenomenal, it's up to us to keep the conversation going beyond just a moment.
Read on to hear Lena Waithe's speak on creating an impact, the importance of mentorship, and why her Emmy doesn't define who she is.
Lena Waithe On Being Your Own Definition Of Success:
I think Denzel said it best, "God gives the reward, man gives the award." And I think they are symbols and also false idols. My Emmy, on purpose, sits on a shelf that's above eye level, so I don't see it every day. It's here; it's a moment, a piece of leverage... Yeah, my name would be written in a book, but the truth is, I am an artist. I don't want to just be someone who won an Emmy. I want someone to go, 'oh, that story she did really spoke to my soul. It made me see myself and not just the beauty, but the scars as well.'
That's the goal. That's the mission.
When I sat down to write "Thanksgiving" [Master of None, Season 2: Episode 8], I wasn't thinking about my Emmy speech, I was thinking about how vulnerable can I be? Okay, now let me go even further. That was always the thing, and even when we were making it, there was power on that set; the spirit was there, like the ancestors were watching us. That's the award. I don't want something to be tangible because I can't take it with me, but the way people feel or the conversation that I have or the connections that I made with people—the eye contact, the conversations—that's something that will live in my spirit that I would take with me.
Lena On Embracing Your Community:
This industry is a mirror for our society, so what they see happening in this industry is a direct reflection of what happening in society. That being said, the playing field is not level in any way, shape, or form. What happens is that every now and then, you get a few people that pop up or ascend and get more focus than everyone else and that's fine, that's why we are a part of it. And for brown people in this industry, we are still playing catch up.
I believe the best way to start change the world is by starting your own community.
So what I try to do is real mentorship, not throwing somebody bone and say, "Oh, here come take this opportunity when you are not ready for it." It's about us that are in the forefront of those that want to be where we are saying what is it that you want, where do you want to be? The mentoring that I do, I tell people that I am going ask you more questions than you ask me.
This is the advice I often give, you want to act, write, and direct, okay great. Which thing do you want to do most? And now based on what they say, I know how to guide them. Have you ever taken a writer's class? No? Fantastic, I know a really cool one. Because of my name, I have invested not just time, but financially. Do you want to be in a writer's class?
Yes, but I can't afford it. Don't worry, I'll sponsor. That's how you make change.
Lena Waithe On Becoming A Mentor While You're Climbing:
Anyone can learn any lesson, you don't have to be a teacher. You don't have to be Oprah to guide. And I think there is an element of looking here [at people who are at a higher level], which is fair, but also look beside you. That is the communion. With my mentees and interns, I put them into writing groups. I say you five over here and you five over there, you all be each other's ride or dies. You all are going to read each other's materials, you all are going to give each other feedback, you all are going to be each other's shoulder when you are sad because that's your peoples.
I met Justin Simeon (Dear White People) in a writer's group and he was working on a project. And I remember hearing his stuff and being like you are phenomenal, we are going to be friends.
That's how we met, by looking here and looking here.
Lena On Being At The Head Of The Table:
GIF by NylonGiphyThere was a time when black people were hot. We had all the movies coming out, then we dried up. Now the cool thing is stuff with people of color. Now we get Dear White People and Moonlight. Now we are getting to the office and they are like well, we want stuff with Black people in it, but it has to have a twist. So now the challenge is on us, don't just come and be like I'm in the door. That's fine, you can be in the room, you're your drive, talent, clocking the ten thousand hours, that's what's going to keep you there.
If you are going to sit at the table, sit at the head of it.
Lena Waithe On Playing Your Part:
[The entetertainment industry] is a human game of chess. And I realize, too, we need to be teaching our people about how to manueuvre it. I don't just want you to be a phenomenal writer, be a politician. And not just any politician, you have to be Barack Obama. I have to be Barack Obama, so that eventually one day, I can be recognized. I got a little more pushing and pulling to do before I can get there. Play your position to the best of your ability, and if you play your position well, eventually you will go forward. And then when the time comes or someone puts a crown on your head, don't just shine, but know how to wear it.
Don't just ask to be the king, you have to know how to lead.
For some time, you have to be a pawn first. That's a part of it because some people come in here like, I want to do it and I'm like okay, you got to crawl before you walk.
There are instances where people will say here is an opportunity, be wary of that. Be wary of the desire, this dream, because it will be a bunch of stuff that feels like nothing.
If you aren't ready for the opportunity, then it's wasted.
Featured image by Kathy Hutchins / Shutterstock.com
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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