“Death, Sex & Money” Offers a Masterclass in Hard Conversations

Anna Sale, host of Death, Sex & Money (Photo credit: Gabriela Hasbun)

Humans have many unique experiences based on our identities, our upbringings, our zip codes, and other facets of our lives that divide us. But there are three things nearly all of us share that we can never discuss enough: death, sex, and money. Since 2014, journalist Anna Sale has been asking a wide array of guests, some famous and some not, about these three broad topics on her incomparable WNYC podcast Death, Sex & Money. With the tagline, “Things we think about a lot and need to talk about more,” it exploded on the scene as Sale was in the midst of a transition. She was getting divorced and she wasn’t about to shy away from using her own experience in those early episodes to help others who were in the midst of transition. She wasn’t an expert talking to us about how to make it through; she was one of us, learning alongside us from the guests she interviewed.

Over the years, as the podcast has become popular and grown its audience, Sale has remained true to the broader themes she set out to explore. Whether she’s asking author Michael Arceneaux about student-loan debt or interviewing Big Freedia about sleeping in New Orleans’s convention center after Hurricane Katrina, Sale has mastered the art of interviewing, leaving space for the emotions of her guests, and expertly guiding conversations. Most importantly, she’s figured out how to get her guests to talk about experiences they wouldn’t ordinarily reveal in polite company, including their money woes. Carrying around debt and fighting to get out of it can feel like a dark secret that’s impossible to share, so listening to Sale interview people about money can feel like a relief or a form of guidance. That’s the beauty of Death, Sex & Money: By virtue of having conversations about the things nearly all of us will face, Sale gives us permission to face these issues in our own lives. Bitch spoke to Sale as about clarifying her podcast’s ethos in her debut book, Let’s Talk About Hard Things, and how she learned how to have hard conversations and help others have them as well.

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When you were creating Death, Sex & Money, how did you decide to focus on these three specific existential elements of life?

It was two things: I was in personal turmoil, in a big phase of transition, and craving more detail from other people about how they’d gotten through periods of upheaval and turmoil, particularly around death, sex, and money. I knew all of us struggled with these big things at one time or another in different ways, in very different ways, but we don’t talk about it with specificity and detail in public conversation enough. [I made] a show where you say, we all deal with these things, all of us are doing it in different ways, and we’re just going to talk about it to see what we might uncover.

You were a reporter before transitioning to hosting a podcast. How did you go before being completely removed from the story as journalists are taught to detailing your own experiences on the show?

It was very uncomfortable. I covered politics. I never walked around saying, I’m objective with a capital O, but as a news reporter, I did think of my job as describing the complicated landscape as I see it and not having a dog in the fight. I’m just going to keep describing how complicated everything is. [But] when I was beginning conversations about tender things—and by tender I mean subjects that are often layered with shame and insecurity—I needed to model how to do it and position myself as someone who was figuring this stuff out alongside the listeners. I didn’t want the show to feel like, “And now here’s Anna who has read all of the books and can now impart all her wisdom on you.” I wanted it to be like, “Here’s this place where we’re all going to get together and talk about how stuff can be really sucky and hard. I needed to say, “Here’s when I have known what to do, here’s when I have messed up, here’s when I’ve failed, and here’s what I’m really afraid of.” I created a space where, if you share something that you’re freaked out about, you’re not doing it by yourself. You’re not doing it alone.

Death, Sex & Money is a narrative podcast whose biggest undercurrent is emotion. How do you balance the interrogation required for interviewing with leaving space for guests to process?

That’s the whole challenge, not just in interviewing but in being in relationship with somebody else. When I’m having a conversation with someone on the show, I want to make sure I’m asking specific and precise questions and that I’m encouraging the person to describe what they’ve been through as concretely as they can. I want to be able to picture it. I want to be able to understand the things they understood at the time, what they didn’t know at the time, what they felt ambivalent about. And it’s not so much about always being able to empathize or be in their shoes. I also want to really understand the ways they might be quite different from me: How they might be much more comfortable with risk than I am or how they might have been living in a different political landscape where the opportunities available to them felt very different than what I’ve experienced. I want to create an environment with my questions where I’m eliciting all of that detail. I don’t want my guests to feel intimidated, but I do want my questions to be precise.

At the same time, I’m always listening for when the wave of emotion crests. If I’m talking to them about something sensitive or that they’ve described broadly in a lot of places—when getting into the details brings up long-buried feelings—I want to be very aware of letting them have the feelings, not digging and pushing but letting them notice the feelings they’re having as they’re describing them. So then they describe the feelings they’re having in the moment as they’re describing a story about something that happened in the past. You don’t often hear it in the show, but I do say to people that if we start talking about anything you feel uncomfortable talking about, then just say so. I don’t want the show to teeter over into the exploitative mining of trauma. I want the conversations to feel like a collaboration, like the person I’m interviewing is giving as much as I’m asking.

Some of my favorite interviews are the ones in which you get people to open up about their debt, whether it’s student-loan debt, credit-card debt, or medical debt, and the ways in which it transforms their lives. We don’t talk much about debt for many reasons. Why is talking about money such an essential part of the show?

Debt is important to talk about because it’s so often invisible, but if you have it, it’s such weight. It can feel like a secret you’re carrying around. The way in which we usually talk about money in our culture is through these totally inaccurate myths that we all know are inaccurate: If you work hard, you’re going to succeed. We also say the only kind of honorable wealth is wealth you’ve earned with your own sweat, and having money through any other means is dishonorable. The other way we talk about money is through status symbols—not with words, but with the cars we choose to drive, the houses we choose to live in, the shoes we choose to wear, the bags we choose to carry, and the degrees we hang on our walls. So it’s very important that we talk more about the debt that comes with those status symbols, specifically student-loan debt, mortgage debt, [and other] housing debt.

It’s important to talk about debt because that’s the way we can acknowledge the ways the economy is working and not working for people. If we just ignore debt and allow ourselves to present how we think we ought to be presenting, you get a distorted picture about who feels like they’re succeeding and who’s not. If you look like you’re succeeding because you’ve got a bunch of degrees, you’ve managed to get into a house that maybe you can’t afford, and you’re bogged down with student-loan debt payments, the way you feel financially is probably a lot different than how you appear.

Death, Sex & Money (Photo credit: Courtesy of WNYC Studios)

It’s interesting that many people seem reluctant to discuss money in detail. They seem more open about death and even sex, but money is where they stumble. Why are some so hesitant to be open about debt and their salaries? How does fear factor into that unwillingness?

The thing that really paralyzes many of us when we have a conversation about money is when you get into detail, you’re going to uncover some real differences between you and your coworkers or your loved ones. Say you’re earning a different amount of money than your siblings are now that you’re adults. You’re going to discover some of you have a lot more options financially. When you don’t know the details, it feels like you’re peers, and many of us are afraid that we can’t explain those differences away once we go into detail. There’s nothing you can say in a conversation if, say, you earn the same amount of money as your coworker but you don’t have student debt. You have a lot more financial options than your coworker does. If you start talking about that and comparing notes, you have to deal with the social discomfort that comes with acknowledging privilege and difference and sitting with that difference instead of just pretending you’re the same.

In the United States, we’ve all wanted to think of ourselves as this great big middle class for so long. We’re either striving to get into it or we’re a part of this middle class, even as the size of the middle class in America is decreasing as people get poorer. We still have this idea that we’re part of this big middle together. So yes, [there’s] social discomfort when you talk in specificity about money, but you should still do it anyway. If you don’t, you’re just carrying around this illusion. It’s shame built on a lack of information instead of just dealing with the discomfort that’s going to arise from looking directly at the information.

You have aired a series of episodes about life during the pandemic—everything from feeling isolated and living alone to being separated from our partners. What has this unprecedented time revealed about how people are thinking death, sex, and money?

So much. [The pandemic was] really important to acknowledge, and what we heard from our listeners is [there was a] stark contrast in your experience if you were able to work from home or if your job required you to keep going in. [There was] just an unequal distribution of risk. When we first went into shelter in place around the country in March 2020, we did a series of conversations with people about dealing with the isolation. We crowdsourced things that were helping people cope while they were at home during the pandemic, and we heard from listeners who were like, “We need coping skills as frontline workers. Don’t forget we also need help.” It has been a time in which each of our lives has been turned upside down, but that has varied really broadly and the suffering has been unevenly distributed.

I talked to a listener named Sherron about having chronic asthma and being a certified nursing assistant. She didn’t know if going into work would [cause her to contract] COVID, lose her life, and not be able to take care of her daughter. So she had the stress of figuring out how to take care of her 13-year-old daughter as a single mom when everything’s shutting down [while] still going into work and facing this risk. The stresses she had just compounded. Whereas for me, I’ve had the stress of having to work from home with two little kids but other than that, I’ve been insulated from risk. I haven’t had any economic consequences. [We also] heard a lot from listeners about the agony of figuring out how to cope with the stress and grief of this time without the physical comfort of being able to gather. That has been very challenging.

There are so many variations on the ways death, sex, and money show up in our lives, and our need to talk about them is not going to go away.

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Whenever you interview well-known people, it’s rare that you trod the same terrain as many other interviewers. What does your preparation process look like?

That’s on purpose. We have a team of producers that works together to prepare for interviews. So if [the guest] is somebody who has been written about a lot or done a lot of interviews, we’ll gather together, read [the stories about the guest], watch as many [interviews] as we can, and [create what] we call a prep document. At the top, we have a timeline of the person’s life that we fill in from all the details we gather from different interviews. I then look for gaps as we create an arc of questions for the interview, like between their late 20s and their mid-30s, this big change happened but I don’t really understand what happened there, so I’m going to ask about that. I look for moments of transition in someone’s life they haven’t talked about before, and then I often uncover something they haven’t talked about. Or I look for some seemingly mundane detail such as: They were trying to become a performer, but they hadn’t gotten their big job yet. What did they do for money back then? By just asking that question, I discover interesting answers that fill in this whole piece that are probably not glamorous and probably not something they talked about a lot in interviews about their success. With people who are successful and well-known, I tend to want to focus on the time in their lives before that happened. I want to know what was going on when they didn’t know if it was going to work out.

How do you keep the show evolving six years in?

The book has been a really fun way to expand the way I think about exploring these big topics. So much of what I do when I’m interviewing pulls on my intuition, but I wanted the book to challenge me to write a mission statement for why having these kinds of conversations is important. What is achieved when you try to have these uncomfortable conversations with people in your life? [Writing the book] was a good exercise in putting words to the important purpose of the show. There’s a lot of important and significant [things] that can happen in conversations where you talk about uncomfortable things. But the gift of having a show called Death, Sex & Money is you’re never going to run out of stories to explore. [Laughs.] There are so many variations on the ways these big things show up in our lives, and our need to talk about them is not going to go away.

I started this show when I was in my mid-30s. I was divorced and I didn’t know if I was ever going to be a parent or get married again. I had all these huge existential questions. Almost seven years [later], I’m married again. I have two little kids. But I have a whole new set of questions about death and sex and money than I did when I was a divorced person who didn’t know what was going to happen in my life. So my own point of view on these stories and questions is continuing to evolve. It’s just such an endless creative well. We’ve been writing, thinking, and telling stories about death, sex, and money since the beginning of literature. There’s [still] a lot to mine there.

This interview has been edited and condensed for clarity and length.

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by Evette Dionne
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Evette Dionne is Bitch Media’s editor-in-chief. She’s all about Beyoncé, Black women, and dope TV shows and books. You can follow her on Twitter.