‘The Interview’: Serena Williams’s Next Challenge

A lot of people reach middle age having achieved some career success and ask themselves: Well, now what? Apparently this happens even if you’re Serena Williams.

Williams, who’s now 42, retired from competitive tennis a little under two years ago. She won 23 Grand Slam tournaments, more than any woman in the Open era and one shy of the record. Her level of fame and achievement — both on and off the court — broke boundaries for Black women and female athletes in general. She is, by most accounts, the best ever at what she did.

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Since retiring, Williams has directed that drive at new projects. She has a venture-capital fund, which mostly invests in founders who are women or people of color, and she just started a makeup line. She and her husband, the Reddit co-founder Alexis Ohanian, also have two small girls: Olympia, who is 6, and Adira, who will turn 1 this summer. So it’s not exactly like Williams has been idle. But the tennis court still calls.

She has gone back to it, in a way, with a new eight-part documentary called “In the Arena: Serena Williams,” which will stream next month on ESPN+. She told me that revisiting her career through the series has really been the first chance she has had to sit back and take in all she has accomplished.

One thing that I was thinking about while watching the documentary is really the kind of amazing competitive spirit that you had, and I’m curious about where that competitive spirit goes or how it changes once you’re no longer playing sports. You’re doing the different projects: the venture-capital fund, the makeup line, you’ve written a children’s book. Did you feel as if you had to find a new outlet for it? For me, it was a necessary thing. I needed to not be done and sit down and wake up and be like: “Oh, my God. What just happened?” It was definitely too fast to throw myself full-heart, full-body into everything, but that’s kind of what I needed to do to survive after I’ve been playing tennis all my life.

Because you were worried about the prospect of not having new challenges once tennis was done? It wasn’t about not having new challenges. It was more around the fact — listen, what you’ve been doing since you’ve been born, do you even know how to do anything else? My whole mission in life was playing tennis. What are you doing today? Practice. What are you going to do? Train. And if you get injured, what are you doing today? Rehab. And that had been my life for over 40 years. You don’t go from a 40-year career to just going: “OK, what are you doing today? Nothing?” [Laughs] So when my career did end, literally the next day I had a huge team meeting for Serena Ventures. We were talking about companies — I had fully taken over. And again, I think it was too much, but it was my way of coping, because I couldn’t go from having purpose for all my life to having no purpose.

Does the “having purpose” aspect of things also include the scheduling and how you’re spending your time? Did you want to maintain a strict or rigorous schedule for yourself? You know what? No. I didn’t know that’s what I was doing. But now I’m wanting to figure out a way to take a break, which I probably should have done earlier, but I don’t know if I would have mentally survived that. I probably would have been back on the court playing tennis. But now I need a breather. I really desperately need a breather. So I’m trying to navigate all that now.

Is there a particular understanding that you want your daughters to have about what you accomplished in tennis? It’s tricky. Olympia told me the other day, “You’re famous.” And I’m like: “Oh, not really. I’m just your mom.” So I don’t know. I just feel like when the time comes — and, honestly, when it’s settled in for me too — I’ll definitely have that conversation with them, and I’ll let them know the potentially, the important, you know, the … I don’t want to be too presumptuous, but the impact I have had on sport and beyond. [Laughs]

Your dad famously saw something in you and your sister Venus when you guys were little and then worked so hard to help you achieve it. Do you see something in your daughters in the way that your dad saw something in you? That’s a really good question. I don’t know. I always look at my dad, and I think, How were you able to do that? Because I’m like, Oh, they’re so cute. I just want them to relax and I don’t want to over-push them. But I would be devastated if I wasn’t pushed, because we wouldn’t be having this interview and there would never have been a Serena Williams. So I feel so fortunate that I had an opportunity to have that extra oomph. But for whatever reason, I’m having a hard time connecting to that extra push, and that’s something I’ve been trying to figure out myself, how to give that extra motivation to my daughters, because it’s definitely worth it, I can confirm from experience.

It worked out pretty well for you! It worked out well. [Laughs] But what do I see? The 8-month-old is so tiny, but Olympia is such a bright light, and she’s so athletic, to the point where it’s just not even humanly possible. Even Venus, she was like, “That kid has more talent than you and I combined,” and she’s not lying. So I can see how my dad may have seen some potential in us. I’m just trying to figure out a way to harness all that. I already told my dad, “Maybe you have to coach her, because I’m too nice.”

You’re too soft. I’m too soft, yeah.

I can imagine it’s an interesting thing that a lot of parents have to think about. You do the hard work and push yourself on some level, maybe so that your kids don’t have to do the hard work. But then you also want them to achieve. You don’t want them to not reach their potential. It also takes a lot of commitment from the parent, and that’s why I have so much respect for my mom and my dad. Because I was like, “OK, Olympia, we’re going to play tennis every Wednesday.” And now I’m like, “Ugh.” [Laughs]

Do you ever talk with Venus about why she still plays? Do you understand why she’s still out there? Venus loves tennis. I think the question would be best answered by her. I do not want to speak for her. But we both love tennis. Honestly, I feel like I would still be playing if I didn’t have to stop and have a family.

In the documentary, you’re reminiscing about winning your first Grand Slam, and you say that after that you really had a bull’s-eye on your back, that the other players on tour were like, “We gotta beat the Williams sisters.” What did you think that was about? I definitely had a red “X” on me. And it was hard. People assume that you’re not friendly, and that’s usually not the case. You’re just there to win, and people don’t really want to talk to winners in a singles sport. It’s like they say, Birds of a feather flock together, and there’s only one winner, so who are you gonna flock with? If I were playing soccer, it’d be a completely different situation, because you have a team of players. I had my mom and my dad, and we kept ourselves really close because we had to. But yeah, I do feel like it shook the world. I mean, come on: A Black girl wins a Grand Slam at 17 years old, and she’s from Compton! Obviously they took notice. Tennis had been dominated by Caucasians, so it was like: “Whoa. We’re having a change in our sport. We don’t like that. This isn’t normal. Let’s not let her win.”

Do you find any of the same racial dynamics at play in — I didn’t say “race.” I didn’t say that it was racial. To be clear, I said that it was a change. You’re going to notice if it was an Asian person winning everything when there were only white people winning before. So I happened to be Black, and it happened to be me, and I happened to win a Grand Slam, and I happened to be young, and it was like: “Whoa. This hasn’t happened since the ’50s, so we’re not used to this, so we want to make sure we make our comeback too.”

Did you see “Challengers”? Yes, I did see “Challengers.” [Laughs]

Thoughts? I thought it was good! I wanted there to be more of an ending. I told Zendaya: “Listen, is there more? Like, I want more. Did they win?” I mean, I don’t want to give away the ending.

Did those interpersonal rivalries and dynamics ring true for you? I thought it was pretty accurate. Sometimes you can become really connected to whoever you’re with, or “codependent” is a better word. I feel like I was codependent with Venus. So I actually felt like there was so much accuracy in there about things that we don’t think about as tennis players or even talk about as tennis players. There’s definitely a lot of co-depending. You can also be a loner in tennis, so I don’t know. Listen, I liked the movie. That’s all I can say.

I saw this news come out of the Trump trial, that you were in the president’s contacts. You guys would talk to each other? I mean, is this what this interview is about?

When somebody has a chance to talk to a president, I’m curious what they talked about. I talk to a lot of presidents. I spoke to Barack, I spoke to the Clintons. I spoke to every president since I’ve been alive, including Ronald Reagan, I’ll have you know.

What do you think they’re looking for in talking to you? What do they want to know? I don’t know, I’m not going to go there.

Fair enough. You know, I am always curious with athletes about the memories that they have from their careers. Does your mind go to the big wins or the losses? I’m the kind of person that be like, “Ugh, I hate it that I lost.” I try to forget my losses, to be honest. I actually refused to go down memory lane during my career, because I always said that’s when you get satisfied. If I’m looking at me and I’ve won, like, 18 Grand Slams, I’d be like: “Oh, my God, that’s amazing. Why am I doing this?” And I didn’t want to have that mind-set, so I never really looked back.

Being the subject of a documentary is obviously something that most people don’t get to experience, seeing your life’s story played back to you in a narrative fashion. What is that experience like? I am always amazed at people and the excitement they have for what I’ve done. I’m just a normal person. You know? I’ve been so in a box of staying focused and just doing the best that I could on that day. So now having the opportunity to hear people talk about it gets me super-emotional. It’s like: “Wow, honestly, I just didn’t know. I just didn’t know.”

Tell me more about that. Because you were so in it you couldn’t see outside of it? Yeah. I mean, obviously I knew. But I would literally win Wimbledon, and I remember having a conversation with my dad, being like, “OK, Dad, that was great, but I know I can win the Open.” I never took much time to settle in my wins. I was always looking for the next quote-unquote “high,” for lack of a better word.

And it was always more competition? It was always the next win.

Do you still find yourself looking for the next quote-unquote “high”? I have so much more excitement now with just relaxing. [Laughs] This has been a process of trying to find my new normal, and now I’m getting to a point where my day ends at 12, and I have a massage at 1:30, and it’s kind of nice to have an opportunity to just take a deep breath in and a deep breath out. I’m trying to enjoy this.

Two weeks later, Serena and I spoke again.

So, one thing that you and I talked about in our first call — [Serena’s daughter interrupts in the background] One second. [Serena to her daughter] What did you say, Olympia? Um, I’ll think about it, but yes.

Was that Olympia? Sorry, I’m just with my daughter today because she’s out of school. So, summertime, yeah.

Well, speaking of Olympia, one of the things that we talked about last time was the uncertainty you felt about how much to try and put your child on a path toward greatness. What are your husband’s thoughts about that? I mean, I assume he wasn’t put on a path to excellence in quite the same way as you were. So does he have the same uncertainty? [Olympia interrupts again] I’m so sorry.

That’s totally OK. I actually think it’s easier for my husband to be more of a motivator than I am, but I’m still trying to find that balance. I always say I wouldn’t trade anything that I’ve done. So why in the world am I not pushing my daughter a little bit more?

Do you find that Olympia responds to being pushed? To be perfectly honest, I don’t think I’ve even pushed her enough to see if she’s responded, which is disastrous! Do better, Serena.

So, [Maria] Sharapova beat you twice pretty early on in your career. Who?

Sharapova. And then you never lost to her again. I think you beat her something like 18 times in a row after that. Did you just decide, This person is never beating me again? Oh, man, you didn’t see it? I think that’s Episode 3.

Oh, they only showed me the first two! God, I’m so sad. You have to see the rest. You gotta wait for it. There was a reason why I didn’t lose to her, and I explain that.

OK. I know you don’t like talking about your losses. But you were so dominant for so long in Grand Slam finals. And then you went zero for the last four. Did that have to do with the pressure of trying to catch Margaret Court’s Grand Slam record? I think so. I should have won two or three of those. One I should have lost for sure. I don’t think, even looking back, I could have won at least one of them. But definitely at least two of them I could have won. It was just too much pressure I put on myself, and I couldn’t relax. That sucks. Honestly, it does. But nothing I can do about it now.

How often do you think about not getting 24? Never actually. I never do. Which is good, right? I had such an amazing career, and quite frankly, I should have had 30. I feel like I could have had way more than 24.

You know, you posted on social media the other day, a little cryptically — Oh, boy, here we go.

That you were ready to hit balls again. What were you referring to? It wasn’t cryptic. I literally am ready to hit balls. I haven’t hit in a long time. It’s my life, and I love it and I miss it so much. I did learn I shouldn’t post it on Twitter, because people think I’m coming back, and I’m like, “No.”

What are you and Olympia going to do today now that she’s off school? What’s the plan? We’re just hanging out all day. I’m going to play Roblox with her later. We had a pedicure this morning. We’re just having a girls’ day.

Retirement sounds good. It’s fun. It’s different. It’s a life I’ve never experienced. You have to understand: For my entire life, since I can remember, it’s been about one thing. I don’t know anything else. And so this is all new to me. It’s like a whole new career. And of course I prefer playing tennis, but that’s because I’ve done it my whole life. Of course you prefer doing something that you’ve done since you could walk. That’s kind of rare in a career. Usually people work to get a career, but I’ve been doing this since I could walk. So definitely a different feeling.

It sounds like you really miss tennis. Yeah, I do. And I like that I miss tennis. I would hate to be like, “Oh, I hated that so much.” That would be such an awful, sad thing for me. Because tennis meant so much to me. And I didn’t realize it meant that much to me, to be honest. I didn’t realize that I would have such an amazing relationship with tennis after it was all said and done. It’s a good miss. It’s like a nostalgia. I love that.

This interview has been edited and condensed from two conversations. Listen to and follow “The Interview” on Apple Podcasts, Spotify, YouTube, Amazon Music or the New York Times Audio app.