Kara Swisher Doesn’t Consider Herself Brave

“People find that they have to think on their feet when they’re doing interviews with me,” Kara Swisher tells me matter-of-factly over the phone. “Smart people like it.” Indeed, watching Swisher do an interview is the journalistic equivalent of watching Michael Jordan sink three-point shots, one after another. (To Mark Zuckerberg: “How do you look at your responsibility as a leader of a massive company with enormous power? Do you think you grok that at this point? Sometimes I don’t think you do. I really don’t.” To fired CNN anchor Chris Cuomo: “I was with my brother last night. Very close to my brother. I would not have helped him if he was in a situation like that. I just wouldn’t.” And to Hillary Clinton: “The stuff you said about Monica Lewinsky. Really disturbing to me and a lot of women. Do you want a redo on that one? Why say something like that, when she’s a young woman, in a position of not power?”)

Swisher doesn’t engage in “gotcha journalism,” but she does bring a fearlessness to her conversations that sometimes makes her subjects squirm in the moment but ultimately come to respect her — and often go back for more. Since that exchange about Lewinsky, Swisher has interviewed Clinton several more times, including their latest conversation, which aired Sept. 29 on her new podcast produced with Vox Media, On with Kara Swisher.

“What I like to do is give people a chance to explain themselves, and I’m fair about it. Then it’s up to them to really make the argument,” Swisher, 59, tells Bustle. “At the same time, when they try to lie or obfuscate, I also point out they’re doing it. I’m like, ‘You’re obfuscating. You’re lying. That’s not true.’”

And in a world full of noise, her cut-the-B.S. approach has an impact. See her interview with former Parler CEO John Matze, who told her on January 6, 2021, as the Capitol smoldered, “I don’t feel responsible for any of this and neither should the platform, considering we’re a neutral town square that just adheres to the law.” Shortly after the interview, Matze lost his job, and Parler was removed from the internet. (It has since relaunched under new management.)

After graduating from Georgetown's School of Foreign Service, Swisher’s ambition was to work in military intelligence or join the CIA. The military’s “don’t ask, don’t tell” policy at the time, however, set her on a different course. “Journalism is a good way to get information out and to analyze and think,” says Swisher, a former New York Times opinion columnist and host of the podcast Sway. “To try to make a difference.”

Below, she talks about challenging our assumptions — about Lean In, the moral obligations of the superrich, and Kim Kardashian’s admonition to “Get your f*cking ass up and work.”

“I talk all the time about how you’ll be dead in 50 years. You only have a short amount of time on this planet. You might as well take advantage of it.”

One of the most remarkable things about you is your utter lack of fear. What advice do you have for people to be braver in their lives?

Well, I’m not unafraid. I’m just appropriately scared of things that are scary, and most things are not scary. I think we put ourselves into situations where we think we don’t have power when we actually do. So a lot of the stuff I do, I don’t consider brave because I’m not scared of these people. I don’t give them that power over me. They find it surprising, especially from a woman.

If you make a mistake, you don’t spiral or over-apologize.

No. Everybody makes mistakes. Men make them all the time, and they turn them into positives, like, “I learned from it,” “It was a pivot,” “There is no failure.” I think people make mistakes and then you move on. I’m good at moving on.

You wanted to join the CIA after college, but being gay was a roadblock. That spurred you toward journalism?

I thought I was going to go into military intelligence. It’s what I studied in school. At the time they had “don’t ask, don’t tell.” It was not possible to live a real — I live a very out life in general. Not just gay out. But I am what I am. I would have loved to serve our country. But it wasn’t to be. Journalism was a good choice, too.

You’ve been called “the best interviewer in journalism.” What makes a good interview?

Being willing to ask the question that everybody wants without being reticent. Listening, of course, is a really important thing. I do plot out interviews, but at the same time, I shift when it shifts. You have to be very nimble. There’s always one or two questions that are so obvious, but I often get better answers out of people. Lots of people interviewed Monica Lewinsky, but nobody did the one I did.

Because you’re willing to ask what no one else will?

Yeah. I’m very interested in what I want to know. And I trust my taste.

I thought about asking you, What can women do to close the leadership and pay gap? But then I thought, that’s the Lean In question. And that’s what makes me nuts about Lean In, that we’re putting the onus on women to lean in rather than attacking the systems that make it difficult for women.

I actually don’t think that’s what the book said. You’re hearing what the media said. If you actually read the book, it’s a little more nuanced than that. So I’m going to push back on the premise of that idea. She wasn’t saying, “If you’re unsuccessful, it’s your fault.” She never said that. Let’s be fair. I’ve written a lot of very critical things about Sheryl. She deserves a lot of criticism for what happened at Facebook. But in that case, I think what she’s saying is, because of the way the system is, this is what you’re going to have to do until we can get in the room and change it.

But nonetheless, you’ve got the systemic bias against women, which is obviously present, especially in pay and everything else. You’ve got to get into positions of power to do something about it, right? Then once you’re there, you have to create a situation where talent is what matters and not gender or race or age or even political affiliation.

You’ve talked about Instagram being harmful to the mental health of young women.

I’ve written about studies. Studies are studies. But go ahead.

Yes, it’s not your opinion. Absolutely. I noticed you haven’t posted on Instagram since March of 2021. Is that deliberate?

Yes, I don’t use any Facebook properties. I just don’t like them. I find them invasive. Until they change the way they collect data on people, I don’t feel like I need to add to their little carnival. I don’t know what the pleasure is there. Essentially, they’re getting everything out of it and I’m not. They have terrible privacy policies, and I don’t feel like helping their business.

Will you take your content down from Instagram?

I’ll just leave it there where it is. I’m not that mad. I used it and then I decided it had no usefulness for me. I don’t need to be performative about my life there. I think it’s performative for a lot of people, and addicting, and I don’t enjoy it. I have problems with Twitter, but it’s a product I enjoy.

What advice do you find yourself giving over and over, and to whom?

Often to women. I have three sons, but I also have a daughter now. I think learning to say no properly and not being pleasing is important for women. You don’t have to please people. You should think about what you want more than what’s offered to you.

I talk all the time about how you’ll be dead in 50 years. You only have a short amount of time on this planet. You might as well take advantage of it. What’s that Hank Williams song, “No matter how I struggle and strive, I’ll never get out of this world alive”?

My dad died when I was 5 so I have a very big sense of mortality. He was 34.

I’m sorry.

That’s OK. It was 50 years ago. He had just gotten out of the Army. He had three kids. He got a big new job. And he died. Life is like that.

You wrote in an Instagram caption, of all places, that parenting your kids “has been my only accomplishment that has truly mattered to me.” How did you do it?

I’m doing it. I have two new kids now.

So how the hell do you do it?

Oh gosh, I’m not a perfect parent, but I do think I’m a very good parent. I let them be who they are. I’m more like, eh, it’ll work out. It’s not tough love or anything like that, but I tend to let them make mistakes. And then I help them when they’re struggling. I often clash with my ex-wife, and also my current wife, when I’m like, “Let them do it.”

My son had a really bad freshman year because of Covid. He was in his dorm all the time and I think, like a lot of kids, he was super bummed. He’s not a depressive person but he’s like, “This sucks!” And I’m like, “Yeah it sucks.” I’m not pretending. Then he wanted to take the year off and work. And I said, “That sounds great.” My life is not his life, and therefore making me happy is really not the same as making a life that he’s proud of.

You’re magically free of neuroses.

I am. Someone asked me, “Have you ever done therapy?” I said, no, not really. I would. I have nothing against it. It helps a lot of people. And there are a lot of people I think should go to therapy. They said, “You’re blocking. You block things.” And I said, “Well, it’s working!” I’m not at all neurotic. You know what I do? I forget things.

Your Pivot co-host Scott Galloway tells his NYU students, “Follow your talent, not your passion.” What do you tell your kids and their friends?

I’m the opposite. I think if you don’t love what you’re doing, you’ll have a miserable life. I really love what I do. There’s that quote, “On your deathbed, you won’t remember your work.” I’m like, why? I love my work.

Did you have rules around cellphones when they were growing up? Like all the tech execs who don’t let their kids go on the internet and send them to Waldorf schools?

That story was overblown. No, I don’t. I make them put the phones down at dinner. I try to make sure they’re not obsessed with them. But I have the same rules about television. It’s just things that occupy your brain. You have to look up. On the street in San Francisco, I come up behind people who are walking around looking down at their phones, and I go, “Hey! Heads up!” And literally every single person always apologizes. They say, “Oh my God, I’m so sorry.” And I say, “You should be. Put it down. You really need to not do that. It’s really uncool.”

I think I need to break up with my phone. Or put it to bed under the little sheet that Arianna Huffington invented.

She tried to give me one. I said, “No. No thank you.”

You once said, “I think people who are sensitive probably don’t do as well with me.” Do you think Gen Z is too sensitive? Too soft? Or do you think they are right to talk openly about things like mental illness and trauma?

I don’t think they are overly sensitive. Listen, everybody’s world is tough, right? I think sometimes we tend to over-index our fears versus our hopes, and that can be very problematic for young people. It’s a tough world. They should be worried about it. We don’t focus on mental illness enough.

But it’s also a trope, right? Like, “Young people are…” Like, all of them? In all parts of the world? One of the problems I have in general is reductiveness.

You’ve covered Silicon Valley since the ’90s. We debate a lot in my house about Jeff Bezos going to space.

Why do you care?

Because I feel like the money could be used for better things. It feels like vanity to me. I know space exploration is vital and important.

It is. It is.

But I want him to fix homelessness and cure cancer and fight for women’s rights before I want him to go with his brother in a cowboy hat to space.

OK, that’s his choice, right? It’s his money. I feel like if he wants to spend the money on that, he should. I don’t think it’s our business to tell people what to do with their money. We spend a lot of time worrying about what rich people should do with their money, and I agree — they should spend it on better things. But they don’t. And I’m not their mama. Where do you actually have impact? With your own children.

And actually, we do need to go to space. With climate change, it’s really important that we focus on other choices for the human race. So if you’re worried about the human race, you should have space exploration on your list of things to do.

What do you think of Kim Kardashian saying, “It seems like nobody wants to work these days?"

I think she’s a hard worker and she probably disdains people who don’t work hard. I’ve interviewed her a couple of times. I like Kim a lot. I think she comes from an era where you just put your shoulder in and go to work.

A lot of young people are thinking, “Why am I wasting my time working?” And I get why they’re doing that. You’re looking at a planet that’s being destroyed. After the pandemic, there’s all kinds of mental illness. Wanting to focus on yourself — that makes sense. But she and I come from an era where work is rewarding. And she loves it. So it’s frustrating for someone like her when people are like, “I only want to work 35 hours. I want work-life balance.” She doesn’t have work-life balance. She just has work. She shouldn’t have clarified it. She should have just let it stand.

Elon Musk said that employees who don’t want to come back to the office can go pretend to work somewhere else.

Yeah, well, I’m on his side. Don’t work for Elon. Don’t complain about it. If you don’t agree with him, don’t work for him.

This interview has been condensed and edited for clarity.