It used to be that the September issue was the most important issue of the year in magazine publishing. I haven’t checked the stats on whether or not this is still the case but the reputation of the September issue is intact. And the September issue for American Vogue is particularly prestigious given the movie and the Anna Wintour of it all. 


On the cover of the September 2022 issue of American Vogue is Serena Williams. And she’s making a big announcement: she will retire after the US Open. We are now in the final month of the tennis career of the greatest to have ever played. And she’s doing it in her own words – this is a first person account, as told via Rob Haskell, these are Serena’s thoughts, her words, her story. 

It’s exactly the right editorial decision and what I appreciate most about how Serena is sharing this decision is that, well, she’s actually still coming to terms with it in real time which means she’s not exactly at peace with it yet – and she’s refreshingly clear about that. About how hard it was for her to arrive here, how she hasn’t been able to talk about it with anyone but her therapist, not her husband, not her parents. Because for a long time she couldn’t say it out loud. And she still doesn’t seem entirely comfortable saying it out loud. There may even be a little resentment there that she had to even make this choice to begin with. 

“Believe me, I never wanted to have to choose between tennis and a family. I don’t think it’s fair. If I were a guy, I wouldn’t be writing this because I’d be out there playing and winning while my wife was doing the physical labor of expanding our family. Maybe I’d be more of a Tom Brady if I had that opportunity. Don’t get me wrong: I love being a woman, and I loved every second of being pregnant with Olympia. I was one of those annoying women who adored being pregnant and was working until the day I had to report to the hospital—although things got super complicated on the other side. And I almost did do the impossible: A lot of people don’t realize that I was two months pregnant when I won the Australian Open in 2017. But I’m turning 41 this month, and something’s got to give.”


Olympia keeps saying that she wants to be a big sister and Serena tells Vogue that she and Alexis Ohanian have been trying for about a year now. Which of course she’s excited about but two things can be true: she can look forward to and prioritise her family but also feel real pain – that’s the word she uses – over leaving tennis. And even though she’s the GOAT, it actually does make her relatable on this particular issue because how many women out there have experienced the same? Having to balance career and family in a way that men don’t have to think about? This is Serena Williams’s reality, a reality that even the best ever can’t escape. 

So it’s understandable that she’s not glitter-coating this announcement, not pretending to be celebratory. And that’s never been how Serena operates anyway – she doesn’t perform for anyone else’s comfort, on or off the court.

That said, she also has a lot going on off the court, including her venture capital firm, Serena Ventures, with “seventy-eight percent of [the firm’s] portfolio [invested in] companies started by women and people of colour”. This is where Serena will be serving aces going forward – or, rather, “unicorns”, as they’re called in the VC world: 

“I started investing nine years ago, and I really fell in love with early stage, whether it’s pre-seed funding, where you’re investing in just an idea, or seed, where the idea has already been turned into a product. I wrote one of the very first checks for MasterClass. It’s one of 16 unicorns—companies valued at more than $1 billion—that Serena Ventures has funded, along with Tonal, Impossible Foods, Noom, and Esusu, to name a few. This year we raised $111 million of outside financing, from banks, private individuals, and family offices.”


Serena Williams, post tennis, still a boss. And a boss who is amplifying the work of entrepreneurial women in particular. These investments will be her wins, group wins, and these are the new champions she will be crowning. 

As for her tennis legacy – she’s well aware of the fairy tale, that of course the ultimate storybook ending to this chapter of her life would be the image of her holding the US Open trophy in victory. But Serena is also a realist. She knows that fantasies don’t always come true, not even when there’s a racquet in her hand. But for her, what seems to be the hardest thing to walk away from is herself, how she sees herself: 

“It’s a good fantasy. But I’m not looking for some ceremonial, final on-court moment. I’m terrible at goodbyes, the world’s worst. But please know that I am more grateful for you than I can ever express in words. You have carried me to so many wins and so many trophies. I’m going to miss that version of me, that girl who played tennis. And I’m going to miss you.”


It’s sad, and it’s OK for her to be sad, it should be sad. She articulates it beautifully: “that version of me”, and that too is what so many women have to reckon with as we move through different phases of our lives, internally and externally, with how we are perceived and how we perceive ourselves. Serena Williams is also going through that right now – and on the biggest stage: on the cover of Vogue and then on center court.