Opinion | How to Have Better Conversations About Hard Things

I’m Ezra Klein, and this is “The Ezra Klein Show.”

So Anna Sale is one of my favorite interviews she’s the host of WNYC’s “Death, Sex, and Money.” And what’s always impressed me about the show she does and the way she approaches it is it she talks about the hard things. She’ll get guests on to talk about death in their family, about their partner losing control of their limbs, about the most personal tragic beautiful embarrassing parts of our lives. And I’ve always admired that the show, it never feels exposed, it never feels like anybody’s doing this for their own pleasure. It feels like conversations that need to be had but aren’t because they’re really hard to have. And that’s a wide range of conversations in modern life. I think if you listen to the show I just did with Will Wilkinson and Natalie Wynn, one way of interpreting that show is politics is full of conversations that are hard and we don’t know how to have. That in this era when we talk about a lot more than we used to and we do a lot more of it in public, the skills we need to navigate these conversations are much more intense than they have been in the past. But nobody teaches them. You don’t take conversation class in school. It’s not a requirement if you go to college. There’s not a lot of training in this. So Anna Sale has just written a book that is simultaneously pulling out the lessons of her show but then also going deeper into the theory and the practice of talking about really hard things. It is called, appropriately enough, Let’s Talk About Hard Things. And it goes through death and sex and money and identity and family and more. And it’s a beautiful book. And it has a lot of advice that is applicable to those of us just having conversations in our lives. And then it is applicable to those of us trying to have public conversation. So I want to have her on the show to have a conversation about having conversations about hard things. As always, my email is ezrakleinshow@nytimes.com. Here’s Anna Sale.

So you see something interesting at the beginning of the book, which is that, we used to have institutions, rituals, and conventions that let us through uncomfortable patches of life. So we were less reliant on individual communication skills. Tell me about that.

That started as something that I have felt very deeply in my own life. I grew up in a pretty small city going to church in a town where there were sort of active civic organizations. I learned how to have a savings account at a bank with a person at a desk.

And you guys were just, like, breathing on each other?

We were. We were.

It’s wild. A different time.

It was a very different time. And I feel like as — I’m 40 years old, I was born in 1980 — as I have become an adult and come of age and started raising my own kids, like, I’ve just sort of noticed the ways that a lot of those places to go for learning how to do a lot of stuff, the places aren’t as obvious anymore. They’re still there. But in my life, I’ve learned like, oh, shoot. How do I talk to my kid about money? Or oh, we’re going to buy a house, like, oh, where do I go to get a mortgage? My first mortgage when I bought a house when I was 25, I went to a bank and talked to a banker. When I bought a house 10 years later, it was all online. I hardly talked to a person. And I think what this means is a lot of figuring out how to navigate. I’ve turned to peers, mentors, friends, family members, like, with that question of, wait, wait, wait, how are you doing this? How do you do this? I’ve also had the opportunity to marry a couple of friends. And it’s such an honor when somebody asks you to do that. Have you ever done that, Ezra?

Yeah. I have. It’s an amazing experience.

It’s such an honor. But after the honor wears off, and you’re like, oh, wait, this is an enormous responsibility that I’m not trained for. What are the words I’m supposed to say? What are the ways that I can make sure I’m honoring their relationship and also honoring the cultures that they’re coming from and what their families have expectations for the ceremony? And somehow I’m the one who’s drafting this in a Google doc. And so I have found that, again, where there used to be more scripts, more places to go to sort of model how to do this stuff, it has fallen on me to find the words to figure out how to handle it. And I think that that is a reason why this book exists, which is to say, our world has changed. And so as that world has changed, there’s more on our shoulders to figure out how to talk in one-on-one conversations, interpersonally to help each other through. We have to do more in our personal relationships because there’s less scaffolding guiding us through.

There’s, I think, a widespread recognition that we’ve lost something as rituals and institutions have faded. But on the other hand, I wonder if some of the nostalgia can be misplaced. So I was thinking in a chapter about death, about religious rituals around death, and how they were both a much better container for mourning than a lot of what I think we have now. But they also imposed a kind of meaning on the event that could be alienating, if you disagreed with it. I mean, it’s very tough to be the atheist at a very religious funeral. How do you think about that tension between the freedom we have to expand conversations now, but the lack of scaffolding as you put it for them?

I’m not arguing that we are in a worse place than we were before. I’m saying we’re in a different sort of place. So our conversations have to function differently. For example, you can talk about death, or you could talk about families, and sex, and relationships, and what is possible now, and how we organize who we love, and how our families work. Certainly, that looks a lot different for people who are my age than people who were born 40 years before. And I think a lot of that is wonderful affirmations of what we each individually desire and want for our lives and have the possibility and choice to make it so. However, there is something that comes with that freedom, which is more responsibility on our own choices and more of our own figuring it out. This book, I hope, is kind of a guide for like, OK, let’s acknowledge that that’s hard. That’s more work. And so here are some ways to start some conversations in your own life to acknowledge that, and also to maybe get some help and offer help to others.

At the core of the book, obviously, is this idea that talking about these things and talking about them well is good. But there’s at least a cultural trope that we just talk more than we ever used to. I mean, you have the stereotype of the silent generation where at least in cultural imagery, men communicate it entirely through grunts and woodworking. And now, we want to talk about sex and money and anxiety and not just talk about it, but throw it on social media. What do you get out of conversation? What do you get out of talking about hard things?

I think you can get a lot of things. I think you can get a feeling of understanding. That’s I think what drives me in my work and also when I’m having a hard conversation with someone I love. If something is off, if I’m not understanding what someone is expressing to me, when you commit to having that conversation with a spirit of like, I want to learn a little bit more. Help me understand. Tell me what that was like for you. That’s interesting. I wouldn’t respond that way. Why are you responding this way? And really, digging in that way, you come away like hopefully seeing that other person in a deeper way and also feeling seen. That doesn’t necessarily mean that the conversation is going to end, and everybody realizing they agree, and there’s no conflict, and everything is great. But it means that you just have a deeper understanding than if you had decided to instead say, like, [SCOFF] I can’t deal with that person. I just don’t want to engage. I’m going to like, just ignore it. I think sort of turning towards the hard conversation with curiosity, you learn important things.

You have a lovely line that the chief skill in any hard conversation is how you listen. So you’ve been doing a show for years and probably living a life as well, where you have to listen in a way that gets people to open up. So what have you learned about listening?

Part of the motivation for this book was I’ve been doing conversations about personal things with people on death, sex, and money for seven years. And one of the things people ask me about is, how do you get people to open up? How do you get them to talk about such personal things? And a lot of it is the spirit of that kind of listening. It’s like, when you feel listened to, it’s an empowering experience. And it’s an unusual experience. And so you may find yourself saying things out loud that you haven’t said before because there was just not the time or space. In this way, I think, that being a journalist and working as a journalist in my adult life has made me a better family member and partner and friend I hope. Because I will find, I will sometimes be mid phone call with a friend that I haven’t talked to in a while, and you sort of get in that rhythm of how you check in, swapping updates. And then I’ll sort of like, just occur to me to be like, oh, wait, let me just ask a more open question, like, what has it been like for you with your two little kids around in this last year? What has that been like? Try to sort of get out of that rhythm of like swapping small talk and exchange, and instead sort of open it up just a little more. And it makes my relationships better. But I think that I’ve learned how to do that certainly because I was taught and got in the muscle of being the weirdo who would shout out the question, like, as a journalist, when you’re taught like it’s your job to ask these big deep questions. That is not how you’re trained to sort of move through polite society. But that’s what I was taught as a journalist. And using those skills in my personal life has made my relationships better.

I really like that image between a conversation where you’re just swapping, and then these are open space questions something. I’ve come to appreciate is a difference, the difference between asking a question where I know the answer I’m going to get and the person knows the answer they’re supposed to give me versus a question where nobody knows what we’re going to get on the other side of It but you do these really beautifully, like, how do you formulate them? What makes an open question for you?

For some reason when you were describing that, I picture that we’re like at the top of a hole and we’re going to go down and spelunk together. Like, we’re just going to like see where we’re going to go together. It has a spirit of exploration. And I think another important thing is to sort of indicate why you’re asking such a big question at the very top because it can be a little bit, like, whoa, that’s a lot coming at me. But I will say things like, I was interviewing someone this week who is a survivor of sexual assault. And she was assaulted when she was a teenager. And she’s now almost 30 years old. And in the last 10 years, she has become very active in sexual assault survivor networks. And I was trying to figure out how we were going to talk about what happened to her when she was a teenager. And she knew that was something we were going to talk about. I first opened that question, can we talk about that night? And can you tell me what happened to you in the words that you would use today, in the words that you use today, for that time? What that did was it opened up this acknowledgment of this was an experience that she didn’t have words for at the time, has sort of acquired language for what happened to her and how she likes to tell her story. And also very much said, this is your story, I am inviting you to frame and give the details that you want to give. Now, that’s an extreme example because that’s a very traumatic event. But I think what was happening in that framing of that question was I was trying to both sort of say, here’s what I am curious to hear about, and also tending to the relationship of our conversation like saying, here’s how I’m thinking about the terms of this conversation, I want you to tell me the words you use now, how you think back on it then, and sort of creating this opening for them this exchange about how she wanted to talk about it.

So let me ask about a very mundane example. If I came to you, I guess as I am currently doing, and said, I want to have a different conversation with my mom today, not the one we have every couple of days where we just check in on what’s going on. What’s an open question you tell me to ask?

I’m going to use an example of a conversation with my own mom. We’re in that phase of life where every few phone calls, she’ll have an update of some people who I knew growing up, who have gotten ill or died. And she will make a joke about how she remembers when she was in this life phase she used to call her mom and get the update of the people who died. And she would sort of feel like, oh, mom’s got another list of people she’s going to tell me. So she’ll make that joke, and then she’ll tell me. And then it’s sort of about like what is that next question when you’re in this sort of update phase, I will say something like, gosh, that’s a lot of people. How do you feel about that? Just having a little opening to move into a little bit of a different rhythm. It’s so much about pacing. Indicate my own emotional response, and then invite her to say more.

Let me ask you about pacing because I think that bears on listening really powerfully. So the linguist Deborah Tannen, who’s great, has this idea of cooperative overlapping, which is where people start chiming in before someone else has done talking. And they’re doing it to push the conversation forward, validate, and say, yes, we do. And it’s interesting. And in some cultures and families, and this is true for mine, that that’s polite. Like, that is how somebody is with you and engaged in the conversation. And then other cultures, and I’ve walked into these conversations, it’s unbelievably rude because it makes a person feel like they’re not being listened to. Like, you can’t wait to start talking over them. And so it brings up this other question, which is, in some ways a pacing question, but in some ways a reading question. There’s, how do you listen to somebody? And then there’s, how do you make sure somebody is feeling listened to? Given that that looks different for different people. You’ve interviewed a lot of different kinds of people. Like, how do you navigate people’s differing preferences here?

You have to pay attention. Like, if — [LAUGHTER] It’s hard. And I think you’ve probably thought about this a lot because it’s like you want to indicate that you’re digging in and you’re really listening. Sometimes, I find myself like, I’ll laugh if there’s something that strikes me as like an absurd moment that they’re saying. And sometimes that can loosen up the person you’re talking to. Sometimes, they’re going to be like, oh, wait, I didn’t know I was making a joke. Is that laugh like — you sort of like reading their reactions as you’re talking. So there is no one way to do this. It’s about paying attention to the way the person is talking to you. I find my own personal style rather than the overlapping to indicate enthusiasm and agreement. Often, I’ll find myself repeating a phrase that the person said to me as a way to move to the next question. Like, I’ll be, like, oh, overlapping, that’s interesting. Like, I wonder how that works in Ezra’s life? Does it sound loud? Or does it sound like — what are the ways that works? So I’ll indicate that I was hearing you while we’re talking, and then open up to another question, rather than sort of breaking in and be like, oh, yeah, that’s how my family works, too, because then it changes the direction of where the person was going when they were talking.

I want to talk about another principle you list before we start going through some of the topics of the book, which just struck me as very deep actually. You write, as a general rule, short sentences help move us through complexity. Tell me about that.

It’s like lesson one in therapy. It’s like, I have all these words for what’s coursing through my body and the things that I want you to understand about what I feel, and then learning like, oh, I am angry. That’s the sentence that you haven’t given words to yet. A lot of this stuff in the book, the hard things, whether it’s navigating distance and family or grief and loss or talking about money. Like, it’s all really complicated stuff, but when you break it down — There’s a sentence that I think about that someone told me when they were leaving a marriage is the sentence, what I wanted has changed. I mean, it’s like simple words but, oh, my gosh, what an immense monumental declaration for yourself and also the consequences for other people. But getting to those short sentences takes a lot of work.

It’s funny children to me or having a child has been a real teacher of this. That I often feel like I communicate better with my toddler than I do with people whom I have very linguistically sophisticated conversations with because at some point he’s just like, I’m hungry. Like, this whole thing. We’re have this whole terrible experience. But the point is I want chocolate. And I suspect we’re all more like that as adults and we’d like to think — when he’s upset, I try to figure out what animal need isn’t being met. And when adults are upset, I try to have a rational conversation about who’s right in this argument. And that doesn’t work super well. And it’s interesting. When I think about this a lot even though I’ve not been able to put into practice in my life, but the ways in which I don’t really ask children to justify why they’re angry after a certain point. But with adults, I really have a sense of proportionality. And I think it is based on a probably wrong view, a way in which our language development enables us to distract from our emotional experience right away and which we’re able to dress things up as very complex, and thought through, and going back five years. And I’m really, we’re just passed. And it was a bad day. And it was maybe a bad week. And it’s maybe been a bad year. Like, the point is I’m angry and I want somebody — or I’m hurting and I want somebody to make me not feel this way.

Yeah. I was writing this book while having a toddler in my household. And there would be moments where I would think like, should we just all watch Daniel Tiger and I don’t need to write this book? Like, Daniel Tiger has songs for all of these things — use your words, here’s what to do when you’re feeling overwhelmed, take deep breaths, and take a minute. I definitely had that thought. And the other thing that I think that happens when we complicate and get older and are trying to process our emotions in real time is either internally or, often in conversation with other people, you’re sort of trying to drive at what the solution is to the problem. What is going to make this feeling go away? What is going to resolve this tension that we are feeling? And I think the spirit that I think is more helpful when going into any kind of hard conversation is a spirit of, what’s going on here? And there’s this line that therapist and activist in the East Bay told me. She does workshops around anti-racism and restorative justice. She told me that she begins her groups by telling them expect and accept a lack of closure. Like, we are digging in, and you are going to not come away with a list of bullet points of solutions for how to make this stuff resolve. And I find that spirit to be so helpful. A hard conversation is about trying to sort of understand more focus on descriptions and sharing experience but not wrapping it all up neatly at the end because when you try to do that, you’re sort of pushing through what actually is the hard thing. And instead, when someone is in grief, for example, if you can just say, I am so sorry, I miss him, too, I am so sorry you are in pain, and I am with you in that. If you can say that instead of, let me know what I can do, it’s a much more powerful emotional experience.

We’ve been talking about how to talk about hard things. And I want to talk about the hard things and what makes them hard to talk about as you do in the book. So let’s begin with death. What makes death hard to talk about? And what are the — and what are the common mistakes people make when talking about death?

I want to say, first, like, one of the things that I found when I was thinking about the organization of this book is like, oh, what do I have to say about death, sex, money, family, and identity? These are all huge things. How can I present a guide for engaging with these hard things? And I sort of landed on this idea of if you start by just thinking about each of these hard things, death, and you say, what is hard about this? And what is intractable about this? What can I not fix in conversation? If you look at that closely, and then go into a conversation about grief and loss and death and aging and diminishment, you’re not having the expectation that you can fix the pain of loss. You’re going in instead with having confronted what’s hard about it and then saying, and I want to show up for this person who is either dying or in grief. Or in my own dying, I want to figure out how to talk about it with the people I love. I want to acknowledge what is happening. And the chapter sort of traces both sort of my own experience with death, but more interviewing people who have encountered it in lots of different ways — pregnancy loss, losing their sister to cancer, as an activist and talking and being surrounded by images of death, graphic images of death all the time. And again, it’s about sort of starting with that like, loss is loss. And it is sad. And it is sad when you are dying and having to say goodbye. But there is something to be gained by just saying, this is hard.

There’s a beautiful point made in that section, and I can’t remember if it’s by you or by one of the people you interviewed, but where you say, people tried to resolve death when they talk to the grieving. They try to say something that gives it meaning, or makes it better, wraps it up. And I got hit with a little bit of a shock of unhappy recognition there, the desire to problem-solve, even a problem you can’t solve. So can you talk about that, about the difference between talking with somebody in a way where you’re trying to give them an answer versus just in a way where you’re trying to be there for them?

Yeah. I mean, it’s really hard. It’s a natural impulse to want to say something to lift pain away from someone you love. It’s a natural impulse. But I think it’s important to pause and remember you cannot do that. When someone is gone who was once here, you are not going to make that less sad. But what you can do is find ways to validate the grief by saying things like, I am so sorry. Grief therapist and writer Megan Devine told me, she lost her partner, he drowned suddenly. And she was in deep grief. And she sort of focused her work on communicating about grief after this loss because she found that people said the most ham-handed things when they were trying to be helpful. And she told me this story about having a friend who didn’t know what to say to her. And instead of sort of pushing to try to figure out the right thing to say, this friend said to her I understand that you may need your own space and I don’t want to crowd you. I also am struggling because I am worried for you even your personal safety. When I don’t hear from you, I worry. So is there a way that I can just text you and say I’m thinking about you? Do you want to talk? Or do you want to be alone? And basically, they created this system where Megan would just text back an asterisk to say I am here and I am taking my own space. And so they found a way to sort of acknowledge like, ooh, we don’t have the words for this. And her friend had her own anxiety about what her friend was going through. And I just thought that was such a beautiful example of someone instead of saying pushing to try to find the right thing, just saying, I don’t know the right thing to say to you right now and I want to love you and care for you in the ways that you need. How about we try this?

So some of this presupposes somebody who is ready to show up and is trying to think about the best way to do so. But anybody who’s gone through loss knows that there are people in your life who, when that happens, the loss is too much for them to look out to and they disappear. It’s too hard. They don’t know what to say. And it’s always a little bit funny who shows up. And that ends up really changing relationships. But sometimes, I think it’s not because people don’t want to show up, but they don’t know how or they don’t feel they have the strength to go into that conversation. So what about that question of how do you prepare yourself to talk to somebody in that kind of loss? How do you deal with your own fear for them or fear of suffering or fear of facing a topic you don’t want to face in yourself?

It’s not just a question of, like, are you ready to face these hard emotions? I think it’s also a question of navigating someone’s dignity. And I think that certainly there are people who, for whatever reason, whatever death and loss they have that comes up when some other death happens, like, they can’t show up in the way that you need or want or thought they might. But I also think it’s delicate how to talk about diminishment and aging and death because we are messy and fragile when death comes up. So I think it’s about figuring out for each particular relationship how to express, care, and to listen to where they are. Maybe they’re really angry about losing someone and figuring out a way to be that person who can listen to their anger. Because especially for women, that can be hard to find a place where you were allowed to just curse what happened. So I think it’s all of those things. But I want to urge everybody to try. There will be people who will disappoint you because they don’t know how to talk about death. But I think each of us can try to show up and say, I’m so sorry.

Speaking of times when we’re messy and fragile, what makes sex so hard to talk about?

Sex is big. And I think what is hard is like, you don’t know if the person is going to want to do what you want to do. I mean that is the heart of what’s hard about and scary and exhilarating about dating. It’s like, I want to spend more time with this person. Do they want to spend more time with me? And what’s hard is like the process of talking about sex is continually going back to that question of, like, do you want what I want? And maybe you’re in the position of not wanting what they want, that’s a hard thing to talk about. Maybe you’re in the position of being rejected, and how to hear that is a hard thing to talk about. But I think sex and relationships, it’s that kind of mystery at the center of, like, are we going to do this thing together?

There’s an idea early in that chapter where you’re talking to a sex worker. Tai, I think is his name. And he says that something that helped him is coming to accept that every kind of sex, whether it includes money or not, is a kind of transaction. Tell me about that idea.

Certainly, if you have done sex work, you are offering a service for money. So that is transactional sex. But he in his life has sex in a lot of different forums. He has sex at work. He has sex with his long-term partner. He has had casual hookups and continues to outside of his long-term relationship. And he was just sort of encouraging me to think about, like, every time you get together with someone, there’s something you want from them and there’s something they want from you, and it doesn’t have to be the same thing for it to be consensual. For example, in a long-term marriage, it might be about one partner really liking that physical closeness because it makes them feel connected and intimate, and there might be another partner for whom it’s very much about physical release. And so you’re getting something different from being together, but it’s still something that you’re doing together. So I found that helpful because I think often we sort of want to flatten what’s happening in sex in a way of, like, everybody’s got to have multiple orgasms, and everything’s got to be just right, and everybody wants the same thing. And I think that sex doesn’t operate like that often in the real world. It happens in a lot of different ways.

There’s another great quote from him where he says, all sex is power-laden even if that transaction is make me feel better about myself. And something that struck me about that is I think, particularly in relationships, we just want to be seen in the space. We don’t want to have to say what it is we want. We don’t want have to try to get what we want. We want to just be given. Because to frame it more as a transaction can, I think, at least culturally cheapen it or so we’re taught to believe. Whereas if you do frame it a little bit more that way, then you can actually discuss it because you can disentangle the things that you want. And maybe then you can actually give your partner more of the things that they want. But that’s a pretty big jump to make. I think the idea that all sex is power-laden and that part of just people what people want is even just to feel better about themselves, it’s a weird in a pretty vulnerable thing for a lot of folks to admit.

I know. Especially when you’re naked with somebody else, like, could you be more vulnerable? But I think it’s going to be helpful to think in all sorts of different contexts where sex is coming up. Like, what do you want right now? Like, what’s this about? Like, what’s this for? I’m a married person for whom sex has been about intimacy and connecting and desire and being with my husband. And it also has sometimes been about, like, we really want to get pregnant. So we’re going to do this. And we’re trying to get pregnant. And it’s a very different kind of sex. I found it helpful to be, like, this is a different kind of thing that we’re doing right now. It doesn’t have to have all the expectation of the kind of sex that we wanted to have when we weren’t trying to get pregnant. Sex when you’re trying to get pregnant is different. So let’s just name that. It’s a little bit awkward and then you’re sort of both in on it. And then you can do what you need to do.

One thing that strikes me just in my own life, younger people I know are much more like this on an average than the older folks I know. And this is kind of move towards consent culture. And if you’re going to have sophisticated versions of consent, it’s more than like, yes or no to the entirety of the experience. It forces people to verbalize what they’re hoping to do, what they’re trying to do, what it is they actually want. And I’m just struck by how much people now who are younger and single, there’s a granularity to the way they talk about their sexual desire, which is not what I remember from being young and single myself in DC. It makes me feel like an old man a little bit. But it does feel to me like there is a real tidal shift in the way this is getting discussed. Now, again, that’s my anecdote from the places I’ve been. But I’m curious, given the more survey work you’ve done on this, if you think that’s true.

Oh, yeah. I think that that’s healthy and great. I certainly have felt pushed when I’m interviewing younger people when they talk about the ways in which they’re not only like sex and consent and continually asking for consent, not just one time but making it a conversation while you’re together. I think that’s really positive. And I think it’s really healthy. And I think you can make it sexy. It doesn’t have to be this clinical, like, is this OK? Instead, it can be this thing where you’re just sort of like encouraging this back and forth while you’re together. And the other thing that I think that I have certainly noticed in interviews with younger people is the ways in which the assumptions about what romance looks like are much wider open, like, talking about monogamy or non-monogamous relationships, or all those sorts of things. There are surveys that show that younger people are much more open to not having just monogamous relationships when they talk about what they want for themselves. But what comes with that is you have to use words. You have to establish what are the expectations that you have for a particular relationship, what do you want, what do they want, do you agree. And yeah, but I absolutely agree that there’s been a huge cultural shift that’s ongoing in what is the appropriate way to have a healthy and respectful and empowered conversation around sex before you do it and while you’re doing it.

What makes money hard to talk about?

Oh, man. This was the hardest chapter, Ezra. I think there’s lots of layers to why it is hard to talk about. The first is our vocabulary is so limited in how we even know where to begin conversations about money. Even with our partners who know what the bank balance is and know the money coming in and out, just figuring out how to talk about it when you have that information is a huge learning process. And then as you move out of those sort of very intimate spheres to friends and colleagues and extended family members, where you’re not talking specifically about dollar amounts but more trying to talk about the ways in which money has enabled you or gotten in the way of making your life look the way you want, like, that is hard because you run into this fact that we don’t all have the access to the same amount of money. And the ways that we talk about that are so sort of usually they fall into these broad hard work equals more resources or more resources means exploitive capitalist. And it’s so hard to even start with the admission and declaration that what each of us has, as far as money, is a result of a lot of history that we had nothing to do with individually — inherited, I mean, depending on what happened to our families before we got here. It’s the luck of where you were in a certain moment both in terms of what moment of a generation of an economy you came into your working life. And it also has to do with work and choice and your relationship to risk and what you’ve built. And I think so often we sort of like go into these reflexive defensive postures of like, if this person is asking you about like why I have so much money, they’re saying that I haven’t worked for it. And that’s just like, let’s open it up a little bit and I’ll take some deep breaths and try to be a little bit more honest about how money works in our lives. And also, share a little bit more about the role of money has played in enabling us to make the life we want. I got into the starting Death, Sex, and Money, one of the reasons money is in the name of the show is because I found it so mystifying as a young person trying to build a journalism career, where I would sort of, I would just like scour interviews for any indication of how someone paid their rent when they were starting out. Did they work two-day jobs and then do this creative thing on the side? Did they inherit money from their grandparents? Did they live with 10 roommates? And there’s just such little acknowledgment of that in our sort of public conversation. I think it’s getting better, but there’s a lot more we can do to sort of like acknowledge the role that money has in how our lives unfold.

I love something you wrote in that chapter where you said that money is like oxygen. It surrounds us flowing in and out of our lives. And when you’re short of it, nothing else matters. And I think that’s also a way in which the media’s entire conversation about money is very skewed. Because the media is not entirely, but it is heavily, people whom are not oxygen-deprived in that way. Not saying nobody is and particularly that young people starting out right now, it’s not a great industry. But a lot of people at the commanding heights of media are fine. And then as you add on to that, we’ve moralized that. We said if you don’t have enough of it, it’s probably your fault. If you do have a lot of it, it’s time to brag. Systematically, like those two things together, real misrepresentation followed by moralization is going to create a very bad societal conversation. And I’m curious if you have reflections on that.

Yeah. I mean, first, your mention of media, I want to shout out to all the news reporters and local newspaper, newsrooms, all around the country for whom financial stability is not a reality. But they’re not the ones driving our national media conversation. But you make me think about this incredible woman I interviewed named Danielle Munoz. And she works at Sacramento State. And she works in student affairs. And her office is sort of the go-to place for a student in crisis. And I wanted to know what does she tell students — Sacramento is a place that the cost of rent has accelerated dramatically, like many communities in California recently. And it’s also a place where there are more and more students. Enrollment is up. So she has all of these students who are just trying to figure out how to find a place to live and pay for school at a time when they’re not primarily working. They’re trying to get through school. And what are those conversations? What does she say to them? And she told me one of the things that she will say when a student walks in, and usually it’s because not that they called up the student affairs office and said, I need help, it’s because they started crying when they were turning in a test and realized they weren’t sure they were going to be able to finish the semester because they needed to work to cover rent. And then the teacher, the instructor, directed them to Danielle’s office. When she sits down with them, the first thing she says is, I’m really glad you’re here and I want to tell you this is a systems issue. And she wants to first say, like, it is not something you have done wrong that you are having trouble making these numbers work. These numbers are really hard to make work. And then she talks about — she used the term radical acceptance with me, which is she wants to say, this is hard and I wish it were easier for you. But this is the situation right now. So looking at the numbers, looking at your student loan package, like, what do we need to do together to deal with the situation right now? And I just found that so sort of like such a useful approach to say, this is not your personal failing. This is about things much bigger than you. But we also have to figure out together what are the steps we need to take so you can cover your rent and get through the end of your finals. And that’s not an easy conversation because, of course, she wishes she could say, here all of these much more affordable apartments that are available to you, and I’m going to solve this problem for you. But she can’t.

When I was reading the book, I was thinking about, which of the five categories of hard conversations that you discuss here do I actually hear the least stuff in my life? Which is the one that is hard enough that people don’t want to talk about it the most? Is there a reason the system is set up to dissuade people from talking honestly about money?

I think it’s a systemic issue and it’s also like a social ease question. I talked to a financial psychologist who says in the book that it’s easier to talk about money with people whom you consider to be in your same tribe. Like, I certainly have found that when I was a new parent and trying to figure out how on Earth child care worked and how people paid for it and where they came up with the money that it takes to pay for child care, I would have these side private conversations with other working parents and say, like, can you just tell me how you’ve made it work? I think that once you get out of that realm of the very, very sort of private conversation that you have with a friend in the backyard or on a phone call or over a drink, there’s a lot of other things that come up, which are if you say out loud like what you make and you know that you have colleagues who make less or who make more, like it’s political. And so you have to be sort of prepared to make that statement. I have found in my own life I’m like, where is my line? What do I feel comfortable saying on the podcast, like, here’s how much I earn every year here’s how much I pay on my mortgage, here’s how much I pay for child care. And for me, I’m sort of like, that’s beyond a certain personal boundary for me. I think in part because I feel like when I have those conversations, I want to have a conversation where I can sort of share it with context and also have the trust built around it for how that conversation is going to unfold. But certainly, there are reasons that the system, as you say, benefits from people not sharing that information. For example, as we’ve seen, there’s a reason why women sharing each other’s salary with each other benefits women in the workplace because they know to ask for more because they figure out what the men are making.

Let’s move to families. And I want to ask this one differently. There’s a great idea in that chapter about family systems. Can you describe that?

Yeah. I mean, I found this sort of useful to think about when you are having a conversation with a family member, it is not you bringing your full whole self and trying to talk with your family member who is bringing their full whole self. Instead, what is happening is that you are talking within the dynamic and within these sort of learned power relationships of how you interact with one another. I am a different sort of person in conversation with my sisters than I am with someone who I work with. Murray Bowen is a family therapist who in the mid 20th century kind of came up with this idea of, how do we create — in a therapeutic setting, how do we sort of try to create an environment where family members can hear each other in a different way? And he set up in his family therapy sessions, he would say, I am sitting here in front of both of you. And I want you both to take turns talking to me. And I don’t want you to talk to one another. And by creating that artificial environment, he was trying to create a situation where the family members could hear each other anew and not be reacting to one another and going into their familiar ruts and patterns, but instead really listening to how they were describing, how their family member was describing their experience. Mess with that dynamic a little bit.

This is a line I’ve always wanted attributed to Ram Dass that if you think you’re enlightened, go spend a week with your family. And that idea of family system strikes me as very relevant to that. There’s this way in which everybody I have ever known reverts back to an earlier version of themselves with their families. It changes the way we communicate. And I wonder why that is. Why is it so hard to grow in your relationship with your family? Why does the way we communicate with our families get locked in an earlier place, even as we change and have maybe developed all these new tools to bring to every other relationship?

It’s not just that we go to an earlier version of ourselves. I feel like we go to the adolescent version of ourselves. We go to the version of ourselves where we are both sort of like known in the family and also trying to break out of how we are known and sort of assert our own personal identity. And I think that speaks to something I really wanted to emphasize about what I think makes family conversations so hard, which is there’s this tension in all families, like there is an assumption of a shared origin, shared history, a shared culture of family because you come from the same place, if we’re talking about families of origin. And then there is the fact that in every family, every person who was growing up, the experience of growing up in a family, is growing up and apart. That separation is a natural part of being a member of a family. But I think the way that it’s experienced by a lot of us is that when you feel that distance or that separation, it can feel troubling, like, why does it not feel like it always has? Why does this family not offer the comfort that it has? There’s this great line in a “Death, Sex, and Money” episode that I have found so helpful in thinking about how I want to parent and also my own experience, like being an adult child of parents. The filmmaker and actor Rafael Casal was being interviewed by Mahershala Ali on the show when I was on maternity leave. And he said this thing about his time of late teenagerhood and the tensions he was feeling with his parents. And he said, he described it as a time when they were navigating their distance. And I just thought it was such a loving way to describe what that feels like when you’re feeling sort of too confined by your family and also not sure how far away you want to get. We were navigating our distance. It just is such a nice turn of phrase that normalizes what happens.

You have a heartbreaking story in that section, but I thought it was a really important story for thinking about how to talk to people and really how to talk about hard things with people, which is the story of a woman whose mother is having paranoid delusions and how she learns that she needs to validate those delusions for the sake of their relationship. Can you talk a bit about that?

Yeah, I really love the story because I think in the ideal of a hard conversation, you are having a conversation with someone who you can both sort of expect to be heard. But there, of course, obviously a lot of relationships in our lives where that’s not possible. And this was a story of a now adult woman but who from her early adolescence was living with her mom who had paranoid Delusions and that would show up in feeling like the neighbors were spying on them and kind of getting very afraid and acting out and causing disturbances for the neighborhood. And so for her entire adult life, this woman has had to sort of figure out how to help manage her mother, her mother’s behavior, and try to keep her safe and also keep the neighborhood association from kicking her mom out of the neighborhood. And she finally got some help by reading a book and sort of encouraged her to think about talking with her mother. And instead of trying to pull her mother out of delusions when she was having deluded thinking. Instead of saying, no, mom, that’s not happening, the neighbors are not after you, you’re safe, you’re fine, like disagreeing with her, instead of doing that, to agree with her mother and say, like, OK, that must be really scary, like what can we do? Like, really trying to make her mother feel like she was hearing what her mother was trying to express. Of course, the young woman, the daughter, understood that she was fibbing to her mother. She was misrepresenting what she thought. But she was listening to her mother and making her mother feel listened to in a way that transformed how they communicated when there was a crisis. And it led to in one of her mother’s hospitalizations as they were talking in this new way. It’s sort of her mother kind of put her shoulders down and sort of allowed her daughter to sort of take more of the leadership in figuring out the health care decisions. And eventually, her mother agreed to sign over power of attorney. So it sort of led to this whole change. And instead of fighting each other, sort of figuring out how to lower that — take that battle out of the way that the dynamic of what was happening when her mother was in crisis. But it required the daughter to just sort of let go of the idea that she could stop this from happening by trying to rip her mother back into clear thinking.

Is there a larger lesson about how to communicate with people on that? Which is, that’s an extreme case, but I think it’s often true that we need to validate other people’s beliefs about reality, even if we don’t agree with those beliefs or even if we don’t agree with those perceptions before they will trust us. Much must be changed by us or allow us to help them.

Yeah, I think it’s a very instructive story for all of us when we’re thinking about family and hard conversations within family and picking our battles. When you’re in a hard conversation, you’ve got to make the choice, like, what is the primary objective right now for me? Do I want to come away from this conversation with the relationship being tended to? Or is it more important that I feel heard and my objective is not to make sure what I’m saying is palatable or something that the person I’m talking to is going to accept? Hasan Minhaj, the comedian, used the line when I interviewed him on the show. He talked about his dad telling him as a kid, do you want to be right or do you want to be together? That’s something you can think about when you’re in a hard conversation. Is it about being right? And sometimes it is. Or is it about being together? And that takes some concessions and silences maybe, even sometimes not letting on where you disagree or think that what the person is saying is not true. But it depends on the circumstance whether you want to be right or together.

I think it’s an important frame for your final chapter, which is about navigating conversations of identity. And that’s a tricky chapter, I thought. I wrote a book about identity. It’s obviously a very politically charged topic. And I think one of the essential questions in those conversations is, are we going to validate each other’s experiences of the world? Does it have to happen in all directions? Are there just certain directions that goes? And what is to be gained by it? Or is this a war to try to assert a singular experience of the world? So I’d like to hear a little bit about how you thought about that framing and what you came away from this chapter, thinking a constructive conversation about identity achieves.

I mean, I think the main thing that I wanted to sort of model with the stories that are in this chapter is I do think it’s really important when we’re talking about conversations about identity, in America, in this moment, that there are some lines that need to be respected as far as like whether you move through the world in a way that has validated and reinforced and propped up your experience as an individual. That you feel seen. And you have seen yourself represented. Or if you’re on the other side of that, and you have not had that experience of being capable of being seen as an individual when you walk into a room, where you feel the way that you are identified, has primacy over how you identify. And I think that has to do with race. That has to do with disability. It has to do with gender. So I wanted to really sort of sit with that. That we have different roles to play in conversations about identity, depending on the experience we have had moving through the world. And one of the means, for me, a white woman who’s financially comfortable, who is married to a man, it’s my role to listen more than talk. I don’t necessarily have to agree with everything that I’m being told, but there are things that people who’ve not moved to the world in the ways that I have things that I have seen and felt and noticed that I have not needed to notice. And so I think that role of listening is more important for people like me. But then I also wanted to get into what does it mean in, like, our most intimate relationships where we are aware of these power dynamics, and we are aware of the ways in which these systems have affected the ways we work in the world. And I interviewed a couple who live in Britain and they had a lot of battles about housework and the labor at home. And for the wife, she felt so much that throughout their relationship, she saw things that weren’t done in their house that her husband just was not trained to see. And because she saw them and her husband did not, based on the world in which they had grown up in, that it became her labor, something that she was responsible for. And they battled over it. And it led to a real crisis in their relationship to the point where she was almost ready to leave the relationship because she just felt so exhausted by all of the responsibilities in their home. And they sort of found a way through talking about this. She would get so angry at him for not seeing these things that she saw. And through talking about it, she began to realize like, oh, some of the expectations I’m bringing about how our house is supposed to look, and how it’s supposed to run, and what it needs to look like, that’s about how I’ve been trained about what is a good woman and what is a good household, and I’m the one who’s in charge of doing this. Because her husband was saying like, it’s OK, you don’t need to do laundry as much as you’re going to do. And actually, like, don’t do laundry for anybody else. We’re going to change it. So you’re only in charge of your laundry. And that it might seem small this sort of very domestic example, but as these conversations about identity and power and who’s to blame and how this all works out in our interpersonal relationships, I thought it was a really interesting example of we have to talk about these systems that were a part of. And then we have to talk about what each of us is carrying because of these different systems of identity. And she found some room to be a little more forgiving of herself and her husband as they talked about changing the gendered expectations that she had for herself.

I found this chapter really interestingly challenging. And it brought up two things. One is that there’s a real difference between approaching a conversation about identity as a conversation about experience versus a conversation about power. Because to some degree, there are answers about who holds power. But experience is relative. People have contrasting experiences. And they’re much more complicated than our power relationships are. And it struck me reading it that there was actually a bit of a tension between that more individual experience of negotiating that you talk about between that couple and that broader conversation about power. Like, even in that exact story, that begins with sort of her applying much more of a power analysis to that relationship a number of times, like pushing him and pushing him, like listen to the podcast and read the articles. And then at a certain point, there’s a bit of a change where she also hears him saying, yeah, it’s actually not what it feels like for me. Like, I don’t just feel like powerful white man in the relationship. I actually feel pretty afraid, afraid I’ll lose you or overwhelmed. And that was an interesting tension, I think, that there’s a — I don’t know. I think there are answers about who holds power in society. But then it’s a problem when you try to apply those answers to individual experiences because people of all races and genders and orientations and religions don’t necessarily have the experience of their identity that you would draw from simply knowing the category of it.

Yeah. Power versus experience is how you’re framing it. But I also think of— there’s thinking about identity in the ways your particular individual identity is constructed based on all these different inputs. And then there’s these broad categories that when we go out into the world, that we feel slotted into and are slotted into. And identity is working at both levels. And when we overemphasize the big categories that we’re slotted into, a lot of people can feel erased and not included, if you feel like you’re someone who straddles the different broad blunt categories. But it’s operating at both levels. And so that’s part of what we have to grapple with when we’re having these conversations about identity. This big complicated stuff, and our words are not very good for describing these things because they are so sort of sweeping on the one hand, and then we want to be very specific about our own identity. And it’s tricky. And it’s figuring out, in that marriage, for example, when you say, I’m going to look at this through this one lens of this power analysis, the husband found himself like, wait, wait, where am I in this? Like, I need you to hear how I’m experiencing this. So we have to hold both of those things at once when we’re having these conversations.

I think that’s a nice place to end and a good lesson for the whole of the thing. So let me ask you our final question, which is, what are three books that have influenced you that you’d recommend to the audience?

They’re all pretty recent books. One came out last year, and it just came out in paperback. It’s called, “Death in Mud Lick: A Coal Country Fight Against the Drug Companies that Delivered the Opioid Epidemic.” It’s by a guy named Eric Eyre, who has been a longtime reporter in my hometown in Charleston, West Virginia, Pulitzer Prize winner. And this book, I just love it because it is a wonderful story of how investigative journalism works. And it also, for me, as a West Virginian, it really got the tone right. It got the tone about what’s been heartbreaking and exploitive and nefarious and also absurd about the opioid epidemic writ large and in West Virginia. But he also shows what’s been happening there as both a function of forces outside West Virginia and people inside who’ve been making choices about what’s going to make them money if they set up a pain pill mill. I just love this book. Another book I’ve really loved recently is “Crying in H Mart” by Michelle Zauner. It’s this memoir of grief and loss, about losing your mother. And also, it’s about her relationship with her husband, who she married when her mother was ill because she wanted her mother to be there at the wedding. It’s about identity. And I’ve been thinking about grief and loss and what happens after a lot lately as we move into this new phase of the pandemic. And I liked having that book sort of shape my thinking about it. And then the third book that I have really loved recently is a new graphic novel by Alison Bechdel called, “The Secret of Superhuman Strength.” And I was so surprised by how important this book feels to me. And again, I think it’s very much about what I needed to read in this moment because it’s about Alison Bechdel’s various exercise regimens over the years and about self-improvement and strength and existential coping. And it’s also about death, and relationships, and workaholism, and what this is all for. And I just found myself feeling really accompanied by all this big stuff that she pulls in in a very enjoyable read.

Anna Sale, your book is the “Let’s Talk About Hard Things.” Thank you very much.

Thank you, Ezra.

So I said a few weeks ago that I was occasionally going to pop in here at the end myself with recommendations when I’m reading something or listening to something or checking something out that I really liked. And what’s cool about that is often these recommendations come from you. One of my favorite things about the emails I got on the show is how many great books I get recommended, music I get recommended. But a couple of weeks ago, when a few of my episodes mentioned that I was reading about octopuses, thank you everybody who wrote in to tell me that you can’t say octopi. That was wonderful. I appreciated getting dozens of emails about that. But somebody wrote in after the Alison Gopnik episode when we were joking about a sci-fi book about an octopuses. I mean, there is such a book. And it’s called “Children of Ruin” by Adrian Tchaikovsky. And it’s the sequel to another book, another sci-fi book, called “Children of Time.” I began reading “Children of Ruin,” and I really had to go back to “Children of Time.” And they’re just both great if you want some really cool biologically informed science fiction or speculative fiction about what hyperintelligent societies based around other kinds of biological organisms would be, I really recommend “Children of Time” and “Children of Ruin.” They’re totally a trip. Just sci-fi at its best. “The Ezra Klein Show” is a production of New York Times Opinion. It is produced by Roge Karma and Jeff Geld, fact checked by Michelle Harris, original music by Isaac Jones, and mixing by Jeff Geld.