

Career advice is something that comes a dime a dozen in an our American overworked hustle culture. It mostly sounds like, "rah rah sleep when you die" or whatever some millennial has said before. Boomers taught us to find a job, and work your way up with that company until you retire from there one day.
Millennials came along and decided that Boomers' way of thinking was dated, especially when factoring in cost-of-living. But truth is, when it comes to Corporate America, working is all about playing smarter, than harder, which is the aspect that Gen-Z has figured out, and damn near normalized. In fact, Gen-Z boldly shows up denouncing all of this, and instead, realized that we need to just get what we want out of these jobs and get tf on.
And they can thank many of those before them, and having access to readily available advice at their fingertips from industry giants.
Regardless, there's still etiquette to working in the States. And if one person knows a thing or two about the topic, it's our good sis Issa Rae. She understands the struggle and decided, for herself, to break out of the mold and take ownership of her career path, whichhhh I guess you can say is working out pretty well. But even she had to learn a few hard lessons along the way. In a recent video with Vanity Fair, she discussed her #LeaveThatJob journey, and the lessons she learned about doing so.
The segment, titledIssa Rae Re-Answers Old Interview Questions, is where she responds to an interview questions she's been asked in the past, with her new perspective. Her previous response is then played, to which she also offers up commentary to her old responses.
Vanity Fair/YouTube
So when she was asked what her "ah-ha moment" was in the Hollywood, of course her current response was full of all gems.
"I guess I'm just more hip to how and why things are made, and who is kind of in charge of saying 'Yes.' But the politics of this business have just become more clear to me in a way that I could at least, intentionally, go around and avoid making things that the studio system thinks is great or poppin. Mind you, I'm a business person and I don't want to make things that suck and that won't sell, but I do want to make things that are very true to me."
She continues:
"And I have found that while Hollywood is like, 'we love original voices, we love originality', all those things, they really don't. So it's just about finding those people who do appreciate that and who are willing to take risks."
But her 2012 response is what made her cringe at the thought of merging what she's learned in the almost decade since.
Vanity Fair/YouTube
"My dumbass..." she responds.
"I thought representation meant like, 'oh I get an agent and manager, money is about to just start coming in, whew finally! It's happened for me!' And I quit my job, and was broke as fuck...so this was not an ah-ha moment, this was a very dead moment for me. It worked out, but I should have held on to it a little longer to save, because whew, there was a struggle."
She then proceeds to give some of the best advice for us looking to move on from jobs to pursue passions with a more mature perspective.
Vanity Fair/YouTube
"Before you quit your job, you should have savings, you should have a plan, and also make sure that you have a support system, whether that's your friends, or a team in place to help you make stuff. You have to have accountability partners to keep you on track."
Because her journey into being a boss was a lane she created on her own, her self-made approach to creativity is why her advice is on so many people's radar--and rightfully so. But her ultimate advice, that she never strays from and has been what she commits herself to, is simple:
"Find [your] people. One of the things that was so important for me was just finding those people who I could rely on and who I could grow with — it's not easy to do things by yourself. Because I'm a shy person, it was hard for me to introduce myself to people and ask for help, but I found that as soon as I started doing the work, people started coming my way."
Issa Rae Re-Answers Old Interview Questions | Vanity Fair
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Featured image by Rich Fury/Getty Images for Teen Vogue
Charmin Michelle is a southern native and creative spirit who works as a content marketer and events manager in Chicago. She enjoys traveling, #SummertimeChi, and the journey of mastering womanhood. Connect with her on Instagram @charminmichelle.
'He Said, She Said': Love Stories Put To The Test At A Weekend For Love
At the A Weekend For Love retreat, we sat down with four couples to explore their love stories in a playful but revealing way with #HeSaidSheSaid. From first encounters to life-changing moments, we tested their memories to see if their versions of events aligned—because, as they say, every story has three sides: his, hers, and the truth.
Do these couples remember their love stories the same way? Press play to find out.
Episode 1: Indira & Desmond – Love Across the Miles
They say distance makes the heart grow fonder, but for Indira & Desmond, love made it stronger. Every mile apart deepened their bond, reinforcing the unshakable foundation of their relationship. From their first "I love you" to the moment they knew they had found home in each other, their journey is a beautiful testament to the endurance of true love.
Episode 2: Jay & Tia – A Love Story Straight Out of a Rom-Com
If Hollywood is looking for its next Black love story, they need to take notes from Jay & Tia. Their journey—from an awkward first date to navigating careers, parenthood, and personal growth—proves that love is not just about romance but also resilience. Their story is full of laughter, challenges, and, most importantly, a love that stands the test of time.
Episode 3: Larencia & Mykel – Through the Highs and Lows
A date night with police helicopters overhead? Now that’s a story! Larencia & Mykel have faced unexpected surprises, major life changes, and 14 years of choosing each other every single day. But after all this time, do they actually remember things the same way? Their episode is sure to bring some eye-opening revelations and a lot of laughs.
Episode 4: Soy & Osei – A Love Aligned in Purpose
From a chance meeting at the front door to 15 years of unwavering love, faith, and growth, Soy & Osei prove that when two souls are aligned in love and purpose, nothing can shake their foundation. Their journey is a powerful reminder that true love is built on mutual support, shared values, and a deep connection that only strengthens with time.
Each of these couples has a unique and inspiring story to tell, but do their memories match up? Watch #HeSaidSheSaid to find out!
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Love Is The Muse: How Skylar And Temi Built A Creative Life Together
When Temitope Ibisanmi DM’d the word “muse” to Skylar Marshai, he knew he was shooting his romantic shot. He didn’t realize, however, that he was connecting with his future business and creative partner, too.
“I was the boyfriend,” Temi says. “Everybody out there knows, you’re the cameraman at that point.”
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.
Today, 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