
How 10 Polyworking Celebs Are Building Multi-Million Dollar Net Worths

Gone are the days when celebrities were boxed into a single career lane. With industries evolving and financial realities shifting, many stars are embracing the polywork trend—building wealth and influence by wearing multiple hats.
Forbes reports, “Polyworking is a growing trend of managing multiple concurrent jobs rather than relying on a single source of income. It heralds a new phase in what has been known as the "portfolio career" or the practice of "slashers"—a concept introduced by Marci Alboher in her book, One Person, Multiple Careers.
Why Polyworking Is the Future
The entertainment industry is no longer just about mastering one craft. Shrinking profit margins (especially in music and acting) and the need for financial security have made it essential for celebrities—and everyday people—to pursue multiple streams of income. Polyworking isn’t just a buzzword; it’s a survival strategy for building wealth and staying relevant.
Take a cue from these stars and don’t be afraid to explore new lanes. Success today means being versatile, creative, and ready to pivot at a moment’s notice.
From acting and singing to launching businesses, here's how some of your favorite celebrities are thriving in diverse spaces:
1. Issa Rae: Multi-Hyphenate Mogul
Issa Rae has mastered the art of polyworking. Known for her groundbreaking TV series Insecure, Issa has expanded into other ventures, including her record label Raedio and, most recently, opening her new restaurant, Somerville, in South LA. In the Naked Beauty Podcast, she shared how wearing multiple hats allows her to express creativity while ensuring financial stability. Her journey proves you can balance art and entrepreneurship.
Back in 2020, Issa told Billboard, "Even from a young age, my mom used to call me bossy. Only now do I realize that I wanted to be that. I wanted to be a boss because, why the fuck not? I liked feeling like I was working or in business. I liked feeling like a leader. And it is not always fun, by any means, but there's an element of accomplishment that I feel in executing projects."
2. Chloe Bailey: The Musician Who Does It All
As one half of Chloe x Halle, Chloe Bailey is a vocal powerhouse. But with the reality of slim profit margins in music streaming, she's stepped back into acting (Swarm, Praise This) and has taken on a bevy of brand partnerships, including a recent one with Pandora. Chloe embodies the spirit of modern polyworking, leveraging her platform to diversify her income and creative reach.
3. Rihanna: From Music Icon to Beauty Billionaire
Rihanna might not be dropping albums as frequently as fans hope, but she’s dominating in other arenas. With Fenty Beauty, Savage X Fenty, and even her role as a mom, Rihanna exemplifies how pivoting into other industries can create lasting wealth. Polyworking has propelled her to billionaire status while redefining her legacy.
She told the New York Times that she knows what she brings to the table, and “knowing that the fashion industry has lacked inclusivity, she’s not planning to back down from being a young, Black woman new to the business.” Rihanna said, “Those factors do come into play, but I will not apologize for them, and I will not back down from being a woman, from being Black, from having an opinion. I do know that the reason I’m here is not because I’m black. It’s because of what I have to offer.” And she offers so much.
4. Donald Glover: The Quintessential Polymath
Donald Glover, aka Childish Gambino, wears multiple hats with ease. From acting (Atlanta, Community) to music and writing, he’s a perfect example of how polywork allows creatives to thrive. Glover’s diverse projects not only showcase his talent but also ensure he’s never reliant on a single stream of income.
Did you know he was also a farmer? He named his nascent company after Gilgamesh, the mythic Mesopotamian hero who angered the gods. “Gilga is like Erewhon for culture,” he told GQ. Donald went on to say, “I want to work with the best people in every medium. To work toward sustainable output. The culture we’re getting from our phones is not high quality. It can be really good sometimes. And fun. But not necessarily high quality. Gilga is the filter for all of that.”
5. Serena Williams: Ace on and off the Court
Serena Williams may have retired from tennis, but her polywork hustle is just beginning. Between Serena Ventures, her investment firm, her beauty brand, and fashion brand S by Serena, she’s proving that building wealth and legacy goes far beyond sports.
The mommy mogul shared on her website that being organized is her best thing. “It keeps me sane and helps me feel like I have some control over a very full life. Tennis is a big part of my life, but I’ve also been dedicating more time and energy to my other passions lately.”
6. Zendaya: Star of the Screen and Beyond
Zendaya’s acting chops (Euphoria, Dune) are unmatched, but she’s also taken on roles as a producer, brand ambassador, and fashion icon. By leveraging her platform across industries, she’s a textbook example of using polywork to establish generational wealth.
We are also waiting for the day she decides to really model because it’s gonna be over for the girls.
When it comes to new projects, the Euphoria star is being the most intentional these days. She told Vogue, “As I get older, I want to be more intentional about the things that I choose to do with my time and the brands I work with. I’ve been approached by similar sports-related brands and, no slight to any of them, there’s just this feeling of openness and care [with On]. They’re already doing the work—I don’t have to tell them to make it more inclusive or more meaningful—they are already doing that. It inspires me; I want to support what they’re doing.”
7. Beyoncé: The Ultimate Multi-Hyphenate
Queen Bey’s artistry is unparalleled, but her ventures like Ivy Park and her groundbreaking "Renaissance World Tour" show how she combines music with business savvy. Her polyworking ensures her influence goes beyond the stage and into fashion, tech, and philanthropy.
Since she’s been at it for decades, she’s had to revisit the blueprint. “There was a time when I was pushing myself to meet unrealistic deadlines, while not taking the time to enjoy the benefits of why I was working so hard,” Beyoncé told GQ. “There aren’t many of us from the late ’90s who were taught to focus on mental health. Back then, I had little boundaries, and said yes to everything ... And now I work smarter.”
8. Tracee Ellis Ross: From Acting to Entrepreneurship, Mastering Multiple Lanes
Tracee Ellis Ross, known for her role on Black-ish, has found success beyond acting with Pattern Beauty, a hair care line designed for textured hair. Ross's goal was to create products that support and celebrate the natural beauty of textured hair.
In an interview with PEOPLE, the founder of Pattern Beauty emphasized the importance of meticulous planning and organization in presenting one's best self. According to Ross, setting up her Pattern headquarters necessitates "mapping out with military precision" to ensure a successful and effective operation. “That is perhaps both an escape and a defense mechanism, and also how I get it all done. But I take the moments: what I call it is being mindful and slow between A and B. So instead of rushing between things, I really allow myself to be present between them.”
9. La La Anthony: Breaking Barriers and Building Empires
La La Anthony, who started as a VJ on MTV's Total Request Live, has expanded her career significantly. Now, she's not only an actor and producer known for roles in Power and Think Like a Man, but also a successful entrepreneur. In 2022, she launched Inala, an award-winning haircare brand.
When talking with The Cut about how she gets it done, La La said, “It’s great to show people that you can do more than one thing, but the challenge is that people often only see you as one thing. So if you’re a radio personality, they only want to see you as that; if you’re a TV personality, they only want to see you as that. I’m all about breaking barriers down and showing people that you can not only be more than one thing — and you can be good at more than one thing. It’s possible. No one should put you in a box.”
10. Keke Palmer: A Masterclass in Balancing Passion and Opportunity
Now, they don't call this former child star Keke "Keep a Job" Palmer for no reason. The 31-year-old has been making polywork work way before wearing multiple hats was as much of a thing. From her breakout role as an actress in Akeelah and the Bee to numerous hosting gigs, including a history-making one as the youngest person to host a talk show with Just Keke at the age of 20.
Making history is just a prerequisite for Keke's polywork success over the years. She even earned an Emmy for her work as a host for the game show Password in 2023, becoming the first Black woman to do so.
When she isn't being a mom, Keke is producing for her digital network KeyTV, acting as a podcaster for her hit podcast Baby, This Is Keke Palmer, being 1/3 of girl group DivaGurl, and even more recently, has added author to her ever-expanding resume with her memoir, Master of Me: The Secret to Controlling Your Narrative. "It’s not just about doing it all," Keke shared with Variety. "It’s about doing it all in a way that feels authentic to you."
Next up for the multihyphenate is One of Them Days alongside SZA, hitting theaters on January 17.
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Featured image by Eugene Gologursky/Getty Images for Fast Company
'Sistas' Star Skyh Black On The Power Of Hypnotherapy & Emotional Vulnerability For Men
In this insightful episode of the xoMAN podcast, host Kiara Walker talked with Sistas star Skyh Black, as he opened up about his journey of emotional growth, resilience, and self-discovery. The episode touches on emotional availability, self-worth, masculinity, and the importance of therapy in overcoming personal struggles.
Skyh Black on Emotional Availability & Love
On Emotional Availability & Vulnerability
“My wife and I wouldn't be where we are today if both of us weren't emotionally available,” he shared about his wife and Sistas co-star KJ Smith, highlighting the value of vulnerability and emotional openness in a relationship. His approach to masculinity stands in contrast to the traditional, stoic ideals. Skyh is not afraid to embrace softness as part of his emotional expression.
On Overcoming Self-Doubt & Worthiness Issues
Skyh reflected on the self-doubt and worthiness issues that he struggled with, especially early in his career. He opens up about his time in Los Angeles, living what he calls the “LA struggle story”—in a one-bedroom with three roommates—and being homeless three times over the span of 16 years. “I always had this self-sabotaging thought process,” Skyh said. “For me, I feel therapy is essential, period. I have a regular therapist and I go to a hypnotherapist.”
How Therapy Helped Him Heal From Self-Doubt
On Hypnotherapy & Empowering Self-Acceptance
Skyh’s journey is a testament to the power of tapping into self-development despite life’s struggles and being open to growth. “I had to submit to the fact that God was doing good in my life, and that I'm worthy of it. I had a worthiness issue and I did not realize that. So, that’s what the hypnotherapy did. It brought me back to the core. What is wrong so that I can fix it?”
Watch the full podcast episode below:
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Women Are (Still) Spelling 'Coconut' With Their Hips. And Guys Are Losing Their Damn Minds.
While prepping for a podcast interview a while back, because I received the questions beforehand, I did a bit of research into one of the inquiries: what are men’s current favorite sex positions? I doubt any of you are shocked by the fact that what continued to pop up (like here, here, and here) was doggy style and the cowgirl position (i.e., when a woman is on top).
When it comes to ridin’, specifically, that got me to thinking about something that was all over the internet a few years ago: women who were advising that you spell “coconut” with your hips, during sex, in order for you and your partner to receive maximum pleasure and satisfaction.
When I asked a few women I know if they ever tried that before, I was surprised to discover that not only had they, but many didn’t treat it as some random social media fad — they actually still do it to this day. Partly, because it’s fun to them and partly because their partner(s) seem to go crazy for it.
Listen, any time something sexual works like a charm, I’m going to shout it out — (late) trend or not. And so, if you’ve never heard of the whole coconut thing, you tried it and forgot all about it, or you just want to try something new/different/else tonight — here’s a reminder, in article form, that coconut-ting is still alive and well, y’all. And the men are all about it!
But First, The Grapefruit Technique
Video Credit: Myem/YouTube (Funny part starts at 2:40)
If this woman is not familiar to you on sight, you ain’t a real one. LOL. Although I know that a lot of people think that the concept of grapefruiting came from the movie Girls Trip (you can see the clip from the film here) that absolutely is not the case. Auntie Angel (whose real name is reportedly Denise Walker) is the creator of the Grapefruit Technique and although I thought that this video came out way earlier, apparently it made its way onto the YouTube streets sometime back in 2014.
If for some reason, you’re not familiar with grapefruiting on any level, I will tell you right now that I had to download this video because it is absolutely NSFW — so you should probably watch it on your lunch break (on your phone with the volume as low as possible) or at home…because chile, the sound effects? Whew, the sound effects. LOL. However, when I sat down to pen this piece, I thought it was hilarious that this video is what immediately came to mind because it seems like, when it comes to “blow his mind sex hacks,” fruit is constantly on the menu.
When it comes to oral sex, it’s grapefruit.
When it comes to ride ‘em cowgirl, it’s a coconut.
What Is the “Coconut” Sex Trend?
@windy_moraba #duet with @mysteri0us.gir1 spell coconut with your waist 😂😂😂
Okay, so what in the world does a coconut have to do with intercourse? Well, for starters, if you and your partner are looking for an all-natural lubricant, coconut oil works well. HOWEVER, do keep in mind that the disclaimer on this is you shouldn’t use it if condoms are in the mix because they can actually cause rubbers to be less effective (silicone lube is a solid bet for condoms, by the way).
There is another way that coconuts are kinda-sorta incorporated when it comes to making sex more pleasurable — and it actually became pretty popular right after COVID lockdown (2021): spelling C-O-C-O-N-U-T with your hips while you’re on top of your partner.
It’s wild how I forgot all about this until a client of mine was telling me how much her husband liked her on top while it wasn’t her favorite thing to do because it felt awkward to her. When I said, “Have you ever heard of spelling ‘coconut’ with your hips before?” — at first, she looked at me like I was crazy and then she busted out laughing: “Girl, no” was her reply.
Hmph. Don’t knock it until you’ve tried it because, as wild as it might sound on the surface, the word isn’t the point so much as the movements that come with spelling it out are.
When you’re moving your pelvis around to make a “c,” “o” or U-turn, not only does it intensify the level of sensation that both you and your partner feel during intercourse, it can also increase the level of blood circulation to both of your genitalia which can make your orgasms more satisfying too.
At the end of the day, spelling “coconut” is simply reminding you that there are more options to riding than simply sitting there while your partner pumps for all he’s worth or you humping up and down like you’re on a pogo stick.
Spelling “coconut” is an easy hack to bring some variety into cowgirling. However…
Honestly, the “Fruit” Isn’t the Point. THIS IS.
From grapefruiting and spelling “coconut” to reading articles that I’ve penned for the platform like “How To Improve The Taste Of Sperm” — fruit and sex are always going to be a winning combination, one way or another. However, the main point of this article isn’t about making sure that you are a master speller so much as providing you with tips that will make the cowgirl position something that you are confident about and you find a ton of fulfillment in doing.
You can make both of these things happen by incorporating the following things:
Stretch beforehand. A charley horse during sex is the worst thing ever — and chile, don’t let it be right before you’re about to climax. SMDH. Yeah, if you want to feel more comfortable when you’re on top, make sure that you stretch beforehand and that you are well-hydrated. That will reduce the chances of experiencing a totally-out-of-nowhere muscle spasm — whether you decide to “spell” during sex or…not.
Bring pillows into the mix. Sometimes riding is a challenge because your partner feels farther away from your body than you would like. Putting a pillow underneath him can help to elevate his pelvis, so that you don’t feel like you’re stretching and straining. Speaking of pillows, a longer one can really come in handy because it can give your knees some additional support as well.
Also, ask him to put his knees up. Speaking of making the “grind” easier for you, ask your partner to put his knees up. That way, your back can recline on his legs as you’re moving your hips around. You’d be amazed how much this one hack can do for you. Straight up.
Add lube. When you get a chance, check out “The Wetter, The Better: 10 Creative Ways To Use Lubricant” and you will automatically see why bringing lubrication into a cowgirl session is an absolute must. It reduces friction. It makes your movements glide with ease. And it’s just more fun. Promise you that.
Lean in. If your partner happens to be on the larger side of life, one way that you can control his depth is by leaning forward into him. That way, your hips can better control how much or little he is inside of you, so that you can get into a position that gives you the sensation that you are looking for.
Get him to multitask. Again, whether you are spelling “coconut” or not and whether you are riding cowgirl or reverse cowgirl — something that is awesome about being on top is it frees your partner’s hands to do, umm, other things. And since it is so much easier to have an orgasm while your clitoris is being stimulated, get your partner to put some of the lube that we discussed earlier on his fingertips, so that he can gently rub on your clitoris while you are riding him. It doesn’t get much better than that!
Don’t wanna spell? Hula Hoop then. What if you try the whole coconut thing and it’s not a favorite for you (or him)? No problem — when’s the last time that you hula hooped? Pretend that you have one of those around your hips and move around that way. I’d be shocked if you ended up feeling “meh” about that option.
5 Guys Tell Me What They Love When Their Partner Is on Top
A part of the reason why I am “team cowgirl” is because it provides a lot of benefits to the woman: she has more control, it tends to be more comfortable for her, it’s a great position for a quickie and the orgasms tend to be that much more — wonderful. However, as I was thinking about spelling coconut, in general, I couldn’t help but wonder what guys thought about it and the cowgirl position overall.
If you’re curious, here’s what five of ‘em said.
1. Braxford. Engaged. 35. “Y’all be spelling up there? Who knew? My favorite thing about when my fiancée is on top is what I think every man likes: the view. It’s a chance to see her entire body and experience it at the same time. Not even doggy style accomplishes that. Damn, where’s my lady at?”
2. Denez. Single. 42. “Do you know how many ‘spots’ you have access to when y’all are on top? Breasts are in my mouth. Hickeys are on her neck. Prop my head up on a pillow and her tummy is getting licked. When a woman is riding you, it’s sensory overload! It’s crazy how each one looks amazing in that position too.”
3. Omar. In a Serious Relationship. 29. “[He said her name yet I’m not going to share it] isn’t a very vocal lover. Her body and technique are insane, so even though I love dirty talk, I’ve learned to compromise — except when she’s on top. She’s not saying much but those moans? And yeah, we tried the coconut thing. ‘Cs’ and ‘Os,’ hell yeah. ‘Ns’ and “Ts’? Nah.”
4. Nolen. Single. 45. “45 isn’t old but it’s old enough for your back to show out on you when you least expect it. My experience has been that women don’t want a lot of thrusting when they are on top, so it’s like having some of the best sex without having to do much at all. Well, aside from trying not to bust too quickly. I take that back: riding is easy on the body; it’s work on the brain.”
5. Ivan. Married. 37. “I like the spelling sh-t because it switches things up. We make a game out of it by her picking a word and spelling out while I try and guess what it is. We also try to see how many words that we can get to before one of us cums. 12 words is pushing it unless it’s like ‘dog’ or ‘cat’ or something. I’ve guessed ‘coconut’ a few times and I get what the excitement is all about. Spelling bee sex: try it.”
Yep. I concur.
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