​Serena Williams returned to tennis four years after announcing she was evolving away from the sport. Despite losing in the first round at Wimbledon 3-6, 7-6, 3-6 to Maya Joint, Williams continues to transcend tennis, exemplifying how a professional athlete can juggle tennis, business, motherhood, and philanthropy. Today’s WTA players aren’t defined solely by rankings or retirement plans; they explore varied paths to success, balancing competing interests much like other professional women.
Former pro Jill Craybas, who retired in 2013 at 39, recalls the uncertainty players felt about life after tennis. She noted fear and concern about what comes next, a sentiment that many contemporary players still encounter. Craybas, now an entrepreneur and tennis commentator, recently completed 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, Give Learn aims to help organizations cultivate leadership through coaching and soft skills, and Craybas was part of the 2025 class. She has observed dramatic shifts in opportunities for female players over the past decade, with many athletes competing well into their mid-to-late 30s and pursuing a wider array of outlets—media work, business ventures, sponsorships, and leadership roles—opportunities she wishes she had during her own career.
The era of the WTA transforming into a multi-hyphenate landscape is well underway. The Williams sisters have been pioneers in this shift, helping to redefine what it means to build a successful career in tennis beyond traditional paths.