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Podcast Host Anna Sale Reveals Personal Experiences To Explore Hard Conversations In Her New Book

Anna Sale smiling next to the cover of her book, “Let's Talk About Hard Things” with flowers
Gabriela Hasbun
"Let's Talk About Hard Things" author Anna Sale

Anna Sale is the host of the WNYC podcast, Death, Sex and Money. On the show, she explores questions and choices so many people have trouble talking about. Now, she's written a book, in hopes of guiding readers through hard conversations about intimacy, grief and identity.

In Let's Talk About Hard Things, Sale opens up about her own life and uses research to put things into context. She spoke with Wyoming Public Radio's Kamila Kudelska about the unusual experience of getting a call from former Wyoming U.S. Sen. Al Simpson when her then-ex-boyfriend had asked the retired lawmaker to help save their relationship.

Anna Sale: He [Al Simpson] just started talking to me about long-term relationships and distance. He was talking about when he was in Washington, and he and Ann [Simpson] had to come back to Wyoming. And then I heard this woman's voice in the background and he said, 'That's Ann. That's my wife.' And I said, 'Well, what does she think I should do?' So Ann got on the phone. And what I most remember about that conversation, besides it being so weird and delightful, was their willingness to say, 'This is not easy. We know that, like, we have been through couples counseling at our church. We have to get through really hard times.' And I was really moved by their willingness to talk about the uncertain and vulnerable moments in their lives as a way to help me feel more comfortable being in that my own uncertain moment. And so, long story short, Arthur and I did reunite and got back together. And it was the beginning of this really wonderful friendship with them. And I interviewed them for one of the first episodes of the show, which was basically telling this story, and also interviewing them about their marriage.

Kamila Kudelska: And so at that point, you hadn't started the podcast, right?

AS: Yeah. No, I was piloting it and trying to figure out what the show was going to be. Yeah.

KK: Did that kind of help?

AS: Yeah, it was like, 'Oh, there is something here,' because I had done sort of traditional journalism, I'd covered politics. So I was not in the habit of putting myself into stories. But that story, having gone through that, it was a way, actually in hindsight, that I could model for the listeners of the show. Like, we're all going through this together. That's the spirit of the show. This isn't a show where I'm going to tell you the choices you should make. This is a show where we're gonna listen to each other and try to help each other through.

KK: Since then, your podcast has grown and flourished. And I guess I just wonder, why did you decide that you wanted to write a book about what you learned?

AS: Yeah, I mean, it started kind of as soon as the show had an audience, something that listeners would say to me was like, 'How do you get people to open up about this personal stuff?' Because the show is about often messy, personal things. And I realized, like, I was sort of, I would describe what I thought I was doing as an interviewer. But I had never really reflected on the techniques that I've learned over the years from just practicing conversation as a journalist. So I wanted to make some space to write about that. And then the other thing I wanted the book to do was to be really clear that like, I recognize, it's really more difficult having a hard conversation with someone you love, or someone in your life than it is with a stranger who hosts a podcast. So the stakes are different. And the risks of what can happen if your relationship changes based on how a conversation unfolds, like, those are different. That said, I really believe that trying to have conversations where you are more honest, and get more clarity about what's happening in your life and in the lives of people you love is worth the effort.

KK: In your intro, you talk about how you want the book to be a companion, rather than, you know, I think a lot of people might be looking at the title, Let's Talk About Hard Things, that it might be like a self-help book or something like that. But I think it's really clear in the intro when you talk about it, that it's more of a companion. But what do you mean, by that?

AS: Well, I think that I've learned from making the show that so much of what we don't talk about often has its roots in the fear of shame and stigma. And so I wanted the book to both be a place where you could sort of get some prompts for opening a conversation that you feel like you need to have. But at a deeper level, I wanted it to feel like, 'Oh, I'm not the only one who's had this feeling about my family, or this experience of grief, or this weird thing that's happened because my friend has way more money than I do,' just normalizing that, that part of what makes hard things hard are these very built-in dynamics. And if you just name what those are, then when you come across them in your own life, they're familiar instead of feeling like you're the first person it's happened to. So that's what I meant by companion. It's just that knowing you're not the only one who's gone through this kind of stuff can make you feel a lot less afraid of just admitting what's going on with you.

KK: The book has lots of elements of what the podcast has, conversations that you have with people on what you've learned from them, but it's also you helping the reader understand, like how they can have that type of conversation. And the podcast doesn't really do that besides listening to people and saying, 'Oh, I could do that.' So it was really interesting for me to see how much like research there is in it, but also there is storytelling. So like, how did you manage to do that?

AS: Thank you for recognizing that, because that was the part of writing the book that was really new and challenging for me, because I, as an interviewer, I think of my chief objective is to listen and to pull out. And I wanted the book to have that but also to be helpful and useful and somewhat prescriptive. And what I kind of came to was like, 'Okay, how about if I have these five chapters of hard things in the book death, sex, money, family and identity.' And I wanted to look at what in particular about these five topics. Like, what is the hard thing at the root of each of these things, and to put that into context with both research and statistics. And so that, I think just recognizing what makes each of these topics hard, it kind of, lets me, let's you and me realize, 'Oh, I don't have to solve the fact that conversation about conversations about money will reveal difference, right?' Like, so much of what we do around how we don't talk about money is because we want to have the illusion of sameness. We all want to pretend like we're part of the great middle class in America. And even as the middle class is shrinking. And if you can get comfortable with the idea of like, well, if you talk about money, it's going to be clear that we all have pretty different money stories that some of which we're responsible for, and some of which is because of luck, or an inheritance or debt that we did had nothing to do with. And so that's where that kind of piece of the research was just to kind of say, like, 'Okay, it's not just you that feels weird around money, here's why you feel weird around it.' And if you just acknowledge this is an element of the conversation, then here's the way you can kind of talk about it without feeling like you're going to fix it. Like you're not going to fix the fact that people have different amounts of money. But also, I think that it does all of us a poor service if we pretend like we do.

KK: Is there a certain part of the book or something that stands out to you? Like, have some people that you maybe talked to that kind of just for us, like, this is why I'm writing this book, like this is why I do this show?

AS: There's so many, I mean, it's like such a good, such a great job to have an excuse to be like, 'I'm curious about you. Can we talk about your life?' I mean, one person who I really loved meeting, who I would not have met if I weren't working on this book is a woman named Anpo Kuwa Win and she lives on the Wind River Reservation. And I actually first met her in Cody, and I reached out to talk to her for my identity chapter. Just about her experience as an Indigenous woman, who's Lakota, but she lives on the Wind River Reservation and is around people who are [Northern] Arapaho and Eastern Shoshone and all sorts of different tribal backgrounds. And to hear from her, like, what all that she has to carry and explain not just about her own individual experience as a Lakota woman, but to explain to anyone who doesn't know anything about Native American people, like broad trends and also what are stereotypes. I just loved knowing her and getting to hear her stories and seeing the really skillful ways she has learned to communicate about really troubling histories that we still live with and legacies we still live with. I'm just really glad I got to get to know her and spend time with her and then to still have her in my life now.

Kamila has worked for public radio stations in California, New York, France and Poland. Originally from New York City, she loves exploring new places. Kamila received her master in journalism from Columbia University. In her spare time, she enjoys exploring the surrounding areas with her two pups and husband.
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