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Anna Sale: Let’s Talk About Hard Things


About this talk

Anna Sale’s podcast, “Death, Sex and Money”, is not afraid to dig into the tough, thorny topics that most of us are eager to avoid. Time and again, in her work and personal life, she has found that it is during these difficult and direct conversations that genuine community and connection begin to take root. In this talk, she shares how to start doing the hard work of listening, sharing, and finding common ground.

Her forthcoming book, called Let’s Talk About Hard Things, will be published by Simon & Schuster in spring of 2021.

This talk was recorded remotely on May 19, 2020.

Anna Sale, Host, Death, Sex & Money

Anna Sale is the creator and host of Death, Sex & Money, the podcast from WNYC Studios about “the things we think about a lot and need to talk about more.” She has contributed to Fresh Air with Terry Gross and This American Life and is the author of the forthcoming book Go There: The Art of Talking about Hard Things (Simon and Schuster). She grew up in West Virginia and now lives in Berkeley with her husband and two daughters.

Full Transcript

Hi, I’m Anna Sale, and first I want to thank you for choosing to watch a talk right now called Let’s Talk About Hard Things, because there are plenty of hard things right now. As I speak to you, we’re a few months into a global pandemic. Nothing is normal right now. I’m in my in-laws’ bedroom. This is where I’m speaking to you from. There’s also loss all around and it’s not clear when we’re gonna be back to anything like stable ground.

But this talk is about how it’s times like these, whether you’re talking about collective suffering, or individual pain, now is the time to sort of lean in and talk about hard things with one another. Because when you do that, you are creating something. It’s a creative process. Something is there afterwards that didn’t exist before, and that’s connection. It doesn’t make hard things necessarily less hard, but it does mean you don’t have to face them in isolation. I do this for a living. I host a podcast called Death, Sex & Money, and for six years, the team and I have tried to really structure conversations with famous people, people who aren’t famous, around these hard things in life. With the intention of drawing it out, so you feel less alone when you’re going through that kind of stuff.

And for the last few years, I’ve been working on a book about how we do that, because I’ve been really struck by the willingness of people to come to our show, and talk about very tender, personal things that you otherwise avoid in polite company. Why do they do that? And I’ve thought about our process, and I’ve also talked to a lot of people who’ve gone through hard things in their lives to get a sense of what kinds of conversations were helpful to them, and how those conversations unfolded. I came to this work through my own moment of really hard stuff.

This is a picture of me when I was in my, what I think of as my late 20s and early 30s malaise. I’m standing here in New York City in 2010. At the time, my first marriage was ending. And I didn’t know what what happening. I didn’t know what I was gonna do next. I didn’t know whether I was gonna stay in New York, what kind of work I wanted to do, how I was gonna support myself as an unmarried woman again. I remember feeling also so tired of spending a lot of time trying to just hold things together, to make the hard things not break apart what was breaking apart. And I was exhausted. And I also felt really lonely.

But that’s the time in my life when I realized that the answers aren’t somewhere else. I am a journalist. My training is if you make enough phone calls, if you look into enough documents, if you try hard enough, you can figure out some really key important answers. This is not that. This work is relational. You have to go at the hard things with people in your life to come out of that isolation. And I learned that when I started dating my now husband, Arthur. I sort of over corrected, and where I was trying to sort of smooth over everything rough at the end of my first marriage, with Arthur I was just letting my angst flag fly free. And I just let him know everything that I was worried about. The questions I had about whether we made sense.

We were long distance. I didn’t know what he wanted. He didn’t know what he wanted. He didn’t know what I wanted. And we talked about it all the time. I talked to him a few years into our relationship about that early period of our relationship, and here’s how he described it.

– [Arthur] Do you remember the time that, I think it was like one of the first times you talked a lot about fears, and I was like, bike shopping in Fort Collins. And I remember standing in this bike shop, like telling the salesperson to wait a minute while I tried my first effort at talking you down off the ledge of not wanting to hang out with me anymore.

– [Anna] Back when I was in Manhattan and I was on my cellphone walking around near 14th street. And, I remember what you said to me was like, look, all you have to decide is if you want to hang out with me right now. If you decide in six months from now you don’t want to hang out with me, that’s okay.

– [Arthur] That was my refrain for the better part of that year, and the next year, and the year after that.

We learned to talk about hard things together. When I say hard things, like there’s a lot of hard things in life, but I think of them in five big categories. There’s death, the fact that we’re all gonna die, and also that there are stakes to the decisions we make and the mistakes we make. Sex, who we choose to be with, the kind of family we want to make. Money, how we survive, how we deal with our ambition, our status. Also family, our relationship to the people we came from, our families of origin, and how that develops and changes as we grow up.

And identity is also a hard thing to talk about. And I mean how we are identified by others, and also how we identify. And I want to pause here and just say like, these things have always been hard. But, I would argue that the onus is more on us as individuals to skillfully navigate this stuff in conversation with the people in our lives. The onus is on us now in a way that it hasn’t been in previous generations. I think about rituals and institutions that used to be sort of stand-ins for dealing with this hard stuff together. Like when I was growing up, when someone died in the community, my mom would take a covered dish over to someone’s front door, and that was a way of saying, I see you’re in pain, I want to help you, I’m here.

I can’t do that with a lot of people I love in my life. I have to sit and figure out, what is the way to respond to this social media post now that I know that this person I went to high school with is gone? I have to figure out, what’s the phone conversation I’m gonna have to reach out? Or when someone is dying, what do I want to say to them? The other thing that’s really different now, like family. As we’ve shed conventions and become more free in what family can look like, and the rules we want to make for our own families. This DIY freedom also has meant that a lot of the onus is on us to figure out how to make those decisions on a one-by-one basis. And if you didn’t feel this before COVID-19, you’ve certainly felt it in the last few months.

I mean, if you’ve had a colleague who’s lost a job, you couldn’t just take them to a bar with all your coworkers afterwards and celebrate them, and sort of talk indirectly about the pain, but support them. You’ve had to figure out how to call them, the email to write, what to say. And if you’re single right now and dating, if you had a good FaceTime date, and then a good second FaceTime date, like you haven’t had touch as a way to also communicate how you feel about this new person. You’ve only had words, and that’s hard. But, talking about hard things can be easier I think when you acknowledge that hard things are hard for a reason. There are hard truths about each of these five things, that if you say I can’t talk my way around this or fix this, then it makes the conversation feel a little bit more possible.

For example with death, for someone who’s died, for someone who’s grieving, you can’t make that go away. That loss is there. You can’t make them feel better. You can just accompany them in that grief. With sex, the hard truth is, no matter how well you talk about consent or what you want, and try to draw out what the other person wants, there’s this, what you’re doing is trying to figure out if you can come to an agreement. So there’s always the risk that someone is gonna be rejected, and someone has to do the rejecting.

That there’s gonna be pain there. You can’t talk your way around that. With money, a really key fact that we like to ignore is people have different amounts of money. As a result of luck, and history, and also effort, but when we talk about money together, we sort of go into this code of aspiration that if you work really hard enough you can make it, and everybody can make it. That’s not true, and that’s not how we should talk about money, and that’s not how you need to talk about money. With family, a really key hard truth that I think that we forget about is, part of growing up is separating from your family of origin. That’s what growing up means.

So when you feel a sense of alienation from these people you come from, from your family of origin, it’s normal. It’s not something that needs to be fixed with words. It’s something that comes with growing up. And finally, identity. The hard truth here is that the way we are identified, and the way we identify fundamentally shift the way we move through the world. My ability to understand what somebody else’s experience is, who is identified or identifies very differently than me is limited. I can’t empathize with them. I’m not gonna be able to understand.

So what I need to do is hear, listen to that perspective, and learn, and learn to incorporate it into my worldview. I thought about this a lot, we did an episode about race and friendship on Death, Sex & Money, and we asked people to tell us stories about their friendships, and when race had kind of come up in a flashpoint. And what was most interesting to me was, in particular in interracial friendships between white people and people of color, we heard a lot about how race was really clearly a factor in tensions that had come up. But it was really hard to talk directly about what was happening.

I want to play you a clip from a woman named Antoinette who told us a story about a white woman that she worked with who was a work friend. They worked together, they got along. And then they had one of those work spats where it was a Sunday, they had a meeting. The white woman said, I can’t make the meeting, let’s reschedule. And Antoinette said, don’t worry about it, let’s just cancel the meeting. And then the white woman starts calling her on her cellphone, and it’s clear that the white woman is thinking, oh my gosh, Antoinette’s mad at me, I want to solve this. Antoinette’s thinking, it’s a Sunday, I’m watching my kid, I also have a leak in my ceiling. I don’t want to answer this phone call right now and have this conversation about her feelings. This is how she talked about it.

– [Antoinette] For me, it’s kind of like when the rubber hits the road sometimes in these situations. The hierarchy of feelings come out.

– [Anna] Tell me more about the hierarchy of feelings. That’s a really useful concept, I think.

– [Antoinette] Yeah, I think, I mean I hate to say it, but I think it’s true that there is a hierarchy of who gets to feel what, and when. And I don’t think that my feelings are valued or acknowledged in the same level in which a white woman’s feelings are acknowledged or valued.

So I asked Antoinette, what do you think would happen if you said to this friend, like, let’s talk about that day and what happened, I want to tell you how it made me feel. She said, actually I’m gonna have coffee with her. I’ve been thinking about it, and I want to talk together about it. And then I said, do you think you’re gonna bring up race? And she said, I don’t think I can lead with that, I’m gonna see if it’s okay to bring it in. And I’m bothered by the fact that I have to lead with her feelings and see if it’s okay instead of my own. I think that’s important to think about, when you’re thinking about a hard thing, a hard conversation that you feel like you need to have or you want to broach.

Let’s think about, what’s the objective of it? Because there’s three kind of different kinds and it affects the way that you structure the conversation. The first is like Antoinette. You want to express something that you feel like has been festering, or a way in which you felt overlooked or unheard. You want to say, like I need you to hear this. Another kind of hard conversation is you want to understand something. You want to reach out to somebody who, like there’s something you think they might have struggled with. You want to know more. You want to kind of also address some maybe confusion you have, or check your assumptions. Just say to them, can you tell me more?

Other kind of hard conversation is shorter, but we also tend to avoid it because it feels a little awkward, and that’s to just like acknowledge when there are hard things. That’s the conversation where you need to say to your friend, “I’m having a hard time in my relationship. I’m having a hard time at work.” Or, say to somebody in your life, like, “Are you doing okay? I notice that you’re having a hard time.” How do you start these conversations? When I think about how I do it at Death, Sex & Money, it’s kind of like two tracks.

I want to think about how I want to listen, and then how I want to speak up. When you’re creating a conversation where you’re asking somebody to talk about something hard, where you need their permission and their buy-in, the first step is always to sort of prepare them, and to explain why you want to have the conversation. When I’m doing this in the context of the show, when a guest is coming on the show, I say like, this show is called Death, Sex & Money. I know, I know that might sound scary. The reason we talk about these things on the show is because we’re trying to get at the variations of all the ways people experience hard things, and create some community around it. And it’s pretty amazing, when you give that sense of like, here’s why I’m coming at you with this, you become collaborators, and you can see peoples’ shoulders go down, and they want to participate, they want to be open, they want to be helpful. And then, just ask.

I use short questions that are specific, that try to get right at what I’m wondering about, or feel like I need to talk about. And then, once we’re in a conversation it’s much more sort of fluid, but I think about it as collecting information, and clarifying. So that’s making sure I’m understanding if somebody’s describing a hard moment in their life. I want to know, oh like, how old were you? Where were you doing for work at that time? Who were you able to talk to about that at the time? Who were you not able to talk to about it at the time? Am I understanding this correctly? Sort of diving in, letting curiosity be my guide. And I try to keep the pace slow, because we are not practiced in talking about this hard, tender stuff. With someone we know, or even people in our own lives.

So I use pauses a lot. Sometimes to just like let things sink in. Sometimes the person I’m talking to will fill that silence. Sometimes it helps me figure out, oh, what do I want to say to acknowledge what this person is telling me? And that reaction is like, sometimes it’s saying like, thank you for sharing this with me, I didn’t know this. Or sometimes it’s saying like, wow that’s really surprising, that’s not how I would have reacted at all. And having that conversation. And then when you’re ending that conversation where you’ve asked someone to talk about something sensitive, I always like to thank them, and just say like, thanks for talking about this with me. Because it is a real privilege.

When you’re having a conversation where it’s more up to you to bring up, you have something to say that you think is gonna be a little hard for somebody to hear, that preparation work is similar. It’s sort of, you want to announce that you’re gonna have a conversation that’s a little bit outside the norm. I need to talk to you about something that’s been really bothering me. I need to talk to you about something that I feel kind of sad about, and I just want to tell you. Just kind of lay that ground for a little bit more openness and listening. I had a therapist tell me once, you can talk about anything if you just think about how you’re gonna start talking about it.

Because you have to get around those blocks of defensiveness, or sort of attempt to, to try to get to that place where someone can really hear you. And then you want to sort of think about, what are they gonna be thinking when I’m coming at them with this? Something that maybe they weren’t expecting. And say like, just kind of acknowledge what their experience might be. So you’re sort of reflecting back, and then you’re redirecting it back to what you want to say. I know this might be uncomfortable for you to hear, but I really need you to hear this. And then once you express yourself, listen back to what they have to say. And, pause, take your time. And then end the conversation, if you can.

Sometimes it’s just like we can’t talk about this anymore, it’s too hot. But sometimes it’s, you know, oh, I hear you, I see it differently. You don’t have to make a resolution for it to be a successful hard conversation. You’re sharing information with one another. I want to end with a piece of tape from the actor Holland Taylor that gets at that. That, like, hard conversations do not fix what is hard in life. I went to her apartment several years ago, and was talking to her about the death of her mother. And she described what it was like to be beside her mother as she took her last breaths. And this is what she said.

– [Holland] And all I can say about death that I felt then and now, what I learned from it is absolutely nothing. It’s like looking at, I don’t know, a volcano or tidal wave, the sky at night. It’s incomprehensible, an incomprehensible experience. Just to be with someone as they die. Astonishing, I could weep now thinking of it, and yet I couldn’t really tell you about it. There’s nothing to tell. A person was there, a person went away. And left themselves behind too, it’s just very strange. Very, very strange. And I got no philosophy from it at all.

I really love how she says that, because she’s saying, this was a really hard thing, I’m gonna describe it to you. I can’t give you any answers. I can’t tell you what it meant. I can’t comfort you as I’m telling you. But I’m gonna describe that I went through this hard thing, and it was bigger than me. That’s what you do when you talk with somebody about a hard thing. You are saying, let’s witness this together, this thing that we have to maneuver around together, and don’t have the answers for.

And you’re creating something when you do that, again. You’re moving out of isolation. You’re moving out of stigma, and you’re creating community, and that’s really, really important. So let’s do it together. Thank you.

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Kelli Anderson
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