Serena Williams couldn’t bear to watch.
As the quarterfinal action of Wimbledon unfolded on Tuesday, Williams tuned in to the tournament she’d won seven times––but not for long. “I just had to turn it off,” she said. “It was too hard.”
Nearly two years into retirement, Williams is finding the role of tennis spectator more challenging than the role of player. That wasn’t the case initially, as Williams said she “watched every single tournament” in the first year after hanging up her racquet.
Not long after ending her tennis career, Williams, who already had one daughter, Olympia, with her husband, Reddit cofounder Alexis Ohanian, became pregnant with their second, Adira, who was born last August. She felt more content with retirement while pregnant, Williams said, but now “it’s definitely harder.”
“I miss it, and I think that’s normal. It’s normal to miss something that you’ve done since the day you were born,” she said.
But when it comes to watching tennis these days?
“Oh my God,” she said. “I just can’t right now.”
Such angst is normal for an athlete transitioning to a post-playing career––particularly one as decorated as Williams, winner of 23 Grand Slam singles titles and the greatest sportswoman of her generation. The ecstasy of high-level competition is not replicable in civilian life.
Which is why Williams, now 42, can’t fully rule out a comeback, no matter how remote the possibility.
“I think as long as I’m healthy, that’s always going to be in the back, back, back, back, back, back, back of my mind,” she said. “I stay fit. I stay healthy. When I’m watching, it’s like, Okay, well, you could be out there too.”
Despite the sense of longing, Williams still believes she made the right decision to walk away from tennis when she did. And she has hardly languished in retirement.
Since playing her final match at the 2022 US Open, Williams has kept busy––with motherhood and her portfolio. Her venture capital fund, Serena Ventures, which she founded in 2017, has continued to invest in start-ups and unicorns, particularly those run by women and people of color. She and Ohanian also have stakes in the National Women’s Soccer League’s Angel City FC and the Los Angeles Golf Club, a franchise in the TGL golf league, which is set to launch next year.
On Thursday, Williams will shift from investment to entertainment when she hosts the ESPY Awards, ESPN’s annual ceremony honoring the best teams, athletes, and moments from the past year in sports.
It’s a bucket list moment for Williams, who said she had always wanted to host the ESPYs but never could due to scheduling conflicts. The ceremony has long been held in the middle of the summer, a time that used to see Williams dominating on the grass courts of Wimbledon. With her playing career wrapped, Williams didn’t think twice when ESPN courted her in the spring to host.
But not every part of the gig has come naturally to her.
“I think as a host you have to make fun of people, and I’m struggling with that,” she told me by phone while in between rehearsals on Tuesday. “I got a line the other day, and I was like, I don’t want to say that. But I also understand that’s part of the job.”
Her hosting appearance serves as a cross-promotional opportunity for ESPN, which will begin airing a new eight-part docuseries called In the Arena: Serena Williams on Wednesday.
