US player Serena Williams warms up prior to playing Australia’s Maya Joint during their women’s singles first round tennis match on the second day of the 2026 Wimbledon Championships at The All England Lawn Tennis and Croquet Club in Wimbledon, southwest London, on June 30, 2026. (Photo by Henry NICHOLLS / AFP via Getty Images) / RESTRICTED TO EDITORIAL USE
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Serena Williams returned to tennis four years after telling the world she was evolving away from the game. Despite her 3-6, 7-6, 3-6 first-round Wimbledon loss to Maya Joint, Williams continues to transcend tennis.
Her ability to juggle tennis, businesses, motherhood, and philanthropy is a testament to the evolution of the professional female athlete. Today’s WTA Tour players are no longer solely defined by rankings or retirement timelines. Instead, like many women with professional careers, WTA players have more options and different ideas about what it means to be successful.
Jill Craybas retired from professional tennis in 2013 at the age of 39. She remembers players approaching her with anxiety about what comes next.
“(They) were kind of like, well, you know, what are you doing, what’s it like,” she said in an interview with Forbes.com. “It was like just a little bit of that uncertainty that you got from them, or a little bit of fear about what to do next.”
Craybas, an entrepreneur and tennis commentator, is in London working and recently celebrated the completion of Give Learn, a 10-month mentorship program that began at Wimbledon in 2024 with the ATP Tour and expanded to the WTA last year.
Founded by James Cluskey, a former professional tennis player, Give Learn helps organizations develop leadership capabilities through coaching and soft skills programs. Craybas was among several WTA and ATP players in the program’s 2025 class.
In less than a decade, Craybas said she’s seen drastic changes in opportunities available to female players.
“Players feel like they can, are playing more often into their mid to late 30s,” said Craybas. “There are a lot more programs that are put in place for players to try different outlets, whether it’s what I’m doing in the media, or, you know, meeting with different people in the business world, or through different sponsorships. I would have loved to have had that when I was still playing.”
Women Players Pivot From Athlete To Multi-Hyphenate
VENICE, CALIFORNIA – APRIL 11: Serena Williams attends WYN Beauty by Serena Williams Pop-Up powered by Shopify at The Lighthouse Venice on April 11, 2025 in Venice, California. (Photo by Stefanie Keenan/Getty Images for WYN Beauty by Serena Williams Powered by Shopify)
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Thirty years ago, a woman’s tennis career traveled a linear pattern: teen phenom, the pro tour, retirement and a few endorsements sprinkled along the way.
Them came the multi-hyphenate career. Williams sisters were trailblazers in the multi-hyphenate career. Serena took acting lessons, appeared in an episode of Law & Order: SVU, and launched a clothing line, all before she turned 30. Venus started an interior design business, owned some smoothie franchises and started a clothing line before she reached her last Grand Slam final in 2017.
When Serena walked onto Center Court, she was more than an aging tennis player. She is a venture capitalist, professional sports franchise owner, podcaster, executive producer on an Oscar-wining film, make-up line entrepreneur and spokesperson for brands across several industries.
Tennis serves as a solid foundation for future business opportunities and having more post-playing days career options is good news for young players like Joint.
“I think the fact that there’s been so many examples now of players that are willing to play in their early to mid to late 30s takes pressure off the young ones to not feel like, you know, if they’re not having the results or being successful in their early 20s, that it’s not the end of the world,” said Craybas. “I think it’s allowing some of these players to realize it’s okay to maybe go to college for a year or two, and maybe even a good step to, you know, find that maturity and learn your independence at college for the first year or two, and then go pro.”
Former pro tennis player and ESPN commentator Mary Joe Fernandez also recognized how many more opportunities there are available to today’s players, including WTA rules changes that make it easier for women to return after having children.
“I like where we are now. I like the longevity of these players. I retired when I was 28. When I tell people that they say, ”Wow, you were so young,” said Fernandez, in an online press conference. “I started when I was 13. . .To come back, there was never even a thought. . I think if I played now, that would definitely be in the back of my mind, that you could take the time to have a child and then come back to the tour.”
Maria Sharapova launched a candy company while she was still playing and has since joined the board of directors of the Moncler Group. Former No. 2 and Wimbledon finalist Agnieszka Radwanska owns a luxury hotel. Naomi Osaka and Coco Gauff started their own talent agencies, while playing.
Despite recent protests over prize money, today’s WTA players make multiple times more than their predecessors. Aryna Sabalenka and Iga Swiatek, both still in their 20s, have already earned more career prize money than Venus Williams. The increased wealth helps finance ventures beyond the baseline.
WTA’s Structural Support Helps Players Build Business
American tennis player Billie Jean King (right), President of the Women’s Tennis Association (WTA), at a meeting with a committee of the the All England Lawn Tennis Club to discuss more equal prize money for male and female tennis players, Wimbledon, London, 26th February 1975. Behind King (right to left) are: WTA executive director, Jerry Diamond (1928 – 1996), tennis player Ann Jones of Wimbledon’s Committee of Management and Air Chief Marshal Sir Brian Burnett (1913 – 2011), Chairman of the All England Lawn Tennis Club. The meeting resulted in an increase in prize money for women from 70 to 80 percent of men’s prizes and the promise of an annual review. (Photo by Daily Express/Archive Photos/Getty Images)
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Five-time Major champion Althea Gibson said she left tennis so she could afford to pay her bills. Thanks to Billie Jean King, WTA pioneers and the Williams sisters, today WTA players are among the highest-paid female athletes in the world. But prize money is only one element of the WTA’s holistic approach to helping players plan for long-term success.
More players are earning college degrees thanks in part to the WTA’s partnership with Indiana University East. The Give Learn program, in only its second year with the WTA, is attracting more players, via word of mouth. The relationship between mentor and mentee includes monthly check-ins, workshops, applied learning, and access to global business events.
Kristina Mladenovic, a former World No. 1 in doubles and a career-high No 10 in singles, also graduated from the Give Learn program. At age 33, Mladenovic is thinking more about her post-playing days.
“The WTA business program helped me a lot just to start again this whole process of thinking of projecting myself and picturing what I could be interested in doing moving forward or not,” said Mladenovic to Forbes.com while preparing for a doubles run at Wimbledon.
After retiring, Craybas launched a chocolate truffle company. She loved her business but felt stuck about how to grow it. After several discussions with her mentor, Val Quinn, former managing director of The Coca-Cola Company Ireland, Craybas decided to scale back her company but not shelve it.
“Val was really valuable at making things simple and clear, as far as getting a little bit more structure, which I didn’t have,” said Craybas. “I was putting so much pressure on myself to figure out what to do, and it was a little bit overwhelming, and she kind of made things a little bit more clear, so that stress was kind of lifted for me.”
Craybas said that the competitiveness and singular focus that athletes sometimes exhibit can lead to stubbornness that might be counterproductive in business.
“I have so many interests, and sometimes if I feel like something isn’t going the way I want it to, I feel like I’m letting it go a little bit faster than I used to, to the point where I wish I could have maybe implemented that more when I was playing,” Craybas said. “As an athlete, you always wish you did better at something, and that’s one area that I felt like I could have let things go a little bit more quickly or easily, and I feel like I’m trying to do that now, which is helping me maybe almost embrace what comes rather than worry about what’s coming.”
The Tennis Players’ Skillset As Business Currency
France’s Kristina Mladenovic reacts after defeating Belgium’s Elise Mertens during the Tennis Fed Cup world group first round match between France and Belgium in Mouilleron-le-Captif, northwestern France, on February 11, 2018. / AFP PHOTO / JEAN-FRANCOIS MONIER (Photo credit should read JEAN-FRANCOIS MONIER/AFP via Getty Images)
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Skills learned on the court translate well to business. Discipline, problem-solving, team management, cross-cultural communication, and leadership under pressure are all sought-after qualities in business leaders.
“I feel like sometimes we underestimate ourselves and just see ourselves as tennis players,” said Mladenovic. “But we develop so many other skills thanks to the sport that afterwards we can really transition and use that part into a new brand or a new job or new work. . .these are all the tools that we’ve been working on.”
Mladenovic said she admires what Serena has done, setting the example for female athletes to broaden their brands.
“I find it very inspiring the way she showed women in general, and the world in general, that you can build so much more around a sports career,” Mladenovic said. “She was pursuing and building on the things that matter to her, and and that she really enjoyed it, and she’s enjoying the process, and I’ve seen her on tour working a lot with her agents, and, and this is something that I believe each one of us needs, keeps us alive, you know, having something that you’re passionate about, and you work towards the goal.”
No matter how far Serena goes in doubles at Wimbledon or if she plays singles at the U.S. Open, she will leave tennis having provided a blueprint, a vision for what a career could be. Meanwhile, the WTA continues to expand its offerings, giving players more tools to transform blueprints into reality.