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.

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 colour, and she just started a make-up line. She and her husband, the Reddit co-founder Alexis Ohanian, also have two small girls: Olympia, who is six, and Adira, who will turn one this year. 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 is screening 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 make-up 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 eight-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.

Loading

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 the film Challengers?
Yes, I did see Challengers. [Laughs]