Jenee Naylor: From Retail to Full-Time Fashion Content Creator

Naylor worked in retail, landing a gig in leadership at Target before going full-time as a content creator and fashion influencer. Through her YouTube channel filled with style inspiration, lookbooks, and fab Fashion Week experiences, as well as other content catering to all the women who aspire to embrace luxury fashion on their own terms, she's amassed a combined online following of more than 900,000.

"I was so committed to my career and just knew deep down that I would make it to the C-suite level. However, when I started my content creation journey, it became difficult to give both Target and my own brand 100%," she told Ebony. "There came a point where I had to choose one because I couldn’t equally excel at both. It’s always interesting and exciting when your passion takes a natural progression and starts to take on a mind of its own."

Ava DuVernay: From Journalism and PR to Filmmaker

Before becoming the award-winning first Black woman to direct a $100 million film, she was a broadcast journalism intern, junior publicist, and PR agency founder. She made a shift to filmmaking at 32. "I kept my publicity job while making my first three films. I knew that as a Black woman in this industry, I wouldn’t have people knocking down my door to give me money for my projects, so I was happy to make them on the side while working my day job," she told Elle in 2018. She didn't officially get behind the camera to create until 2010's I Will Follow, and has gone on to be a powerhouse behind films including Selma, A Wrinkle In Time, When They See Us, and Queen Sugar.

“I was sober about the industry that I was getting into and what my place was in it. There was really no place," she told CBS News in a 2022 interview. "For me, it allowed me to be risky. People say brave, but it wasn’t brave. It was kind of like, you know what, they’re probably going to kick me out of movies anyway, so why don’t I just go for it and say what I want to say?”

Michelle Obama: From Law to Former U.S. First Lady to Best-Selling Author

Known as the "Forever First Lady" by many, Michelle Obama has staked her claim as a pioneer and the powerhouse better half of our first Black president. But before her husband would win the P.O.T.U.S. seat, she practiced intellectual property law and ended up looking, according to reports, for a way to dig deeper into community involvement. In 1991, she took a job as assistant to the then-mayor of Chicago, Richard Daley, and then held several prominent public service positions in the city. She also worked in education, advocating for the leadership and advancement of young adults, before going full-time into political campaigning during Barack Obama's first successful run for president. She's since remained involved in advocating for communities (via speaking engagements, partnerships, and philanthropic work), hosted "The Michelle Obama Podcast," wrote best-selling books, and co-founded Higher Ground Productions, which is behind Netflix hits including "Becoming," "Rustin," "Working: What We Do All Day," and "Fatherhood."

“For me, becoming isn't about arriving somewhere or achieving a certain aim. I see it instead as forward motion, a means of evolving, a way to reach continuously toward a better self. The journey doesn't end,” she wrote in Becoming.

La La Anthony: From MTV VJ to Actress

If you're familiar with the heyday of MTV VJs, then you know Alani "La La" Anthony was among the forerunners in media, hosting hit radio and T.V. shows since the '90s and into the early 2000s. Later, she'd shift focus, appearing in now-cult classics like Two Can Play That Game and You Got Game.

Since then, she's enjoyed major success in Hollywood, starring in Power, the Think Like A Man franchise, The Chi, BMF, and many more T.V. and film hits. “To this day, with my acting career, you’ll still have people who are like, ‘Oh, that’s La La from MTV,' " she said in a 2020 Essence interview. "And it’s like, well, that was a huge part of my life, but I’ve evolved since then. I’ve moved on since then. I’ve worked really hard, but sometimes I feel like because I was known for something else, I have to prove myself in these new spaces even more than the next person.”

Courtney Adeleye: From RN to Obali Founder

Adeleye was a registered nurse who saw a gap in the haircare market and decided to fill it. She launched The Mane Choice in 2013, a brand that would later land in Target, CVS, Walmart, and other stores, earning the company millions. MAV Brands acquired the company in 2019, and Adeleye entered into her next super-successful career transition as CEO and founder of Obali, a direct-selling umbrella company offering wellness, haircare, fashion, and feminine care products.

"We can all agree that no matter what your age, there's experience there that's going to give you the jump on entrepreneurship or innovation. And I have to continue doing that, to continue innovating, she told xoNecole.

Tiffany Aliche: From Preschool Teacher to The Budgetnista

Aliche was a preschool teacher when the financial fallout after a layoff prompted her to use her own journey to financial freedom to empower others. Her financial literacy platform, via books, events, speaking engagements, and her podcast, Brown Ambition, has helped millions of women get out of debt, meet their savings goals, become homeowners, and shift their thinking about wealth building. She's also advocated for financial literacy education in schools, successfully working with New Jersey legislators to pass a law requiring coursework for middle school children to learn the fundamentals of managing finances.

"I lost everything — my job, my income, my home. And it was so traumatic for me that I said, “I’m never, ever, ever going back there," Aliche said in an interview with The Cut. "Now I own my job, so I don’t worry about that."

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