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Brian Lehrer: It's the Brian Lehrer Show on WNYC. Good morning again everyone. As someone who talks to people for a living, there's a question of the types of conversations we have. On this show, we talk about all sorts of things with reporters and academics and you, the listeners and activists, and the mayor and your senators and other elected officials, we deal with a lot of hard questions, but what about hard personal conversations? The kinds of talks we may have with our aging parents, our grieving friends, our partners, right before a split, our colleagues at work, people have different backgrounds from us who we might come in contact with whatever backgrounds we are from.

In her new book, Anna Sale, describes it like this, "Hard conversations in real life, are a lot trickier than they are on a podcast," well, I'll add on a live radio show. She writes, "For one they don't take place in a radio station between strangers with an editing crew at the ready, they occur in real-time with the people we love when our emotions are tangled and raw." Of course, Anna also talks to people for a living. Anna Sale is the host of the WNYC Studios podcast, Death, Sex, & Money, as many of and now she's the author of the brand new book, Let's Talk About Hard Things. Welcome back to the show Anna and congratulations on the book, I'm so excited for you.

Anna Sale: Thank you, Brian. I'm so glad to talk to you about it.

Brian: Tell us more about the kinds of hard conversations you decided to write a book about.

Anna: I was like, "Hard things, how am I going to contain all that it brings up?" I decided to focus on five big chapters and they are death, sex, and money, things that we've long explored on our show. Then I wanted to add family and identity because I wanted to tease out those, in particular because I think that those relational dynamics are different than generally talking about death, sex and money when you're talking with someone with whom you share a deep family history, but maybe feel some separation how to talk about that.

Then, with identity, I wanted to get at how do you have a conversation with someone different than you? How do you account for power differences and blind spots? Who should listen more and how do you ask questions? Those were the five that I settled on.

Brian: You're going to have to expand the name of the podcast, death, sex, money, family, and identity with Anna Sale.

Anna: Maybe we'll just call it all the hard things and people will be like, "Oh, I want to listen to that."

Brian: That's right. Let's delve into the really tough stuff. I'm going to choose that over light entertainment or too many characters to fit in the promo space. Let's pick one of those. People will like I think to hear a little personal anecdote from you, especially if they're regular Anna Sale listeners. You write about your move to New York City, you grew up in West Virginia, eventually finding work here at WNYC, why was that a moment in your life that sparked difficult conversation?

Anna: Oh, it was so much transition all at once. My move to New York City was actually not my choice. I was married at the time. It was my first marriage. My ex had been a civil rights lawyer when we got together and when we got married and then he turned 30 and realized like, "Oh, I actually really want to make movies." I knew he was this creative artistic soul, that was part of the reason I loved him, but he wanted to make a big career change and so he applied to NYU film school, he got in and in 2009, we headed for New York City. You'll remember 2009 was a tough job market for journalists.

Brian: Just a little bit.

Anna: Just a little bit. For me, it was this huge leap of faith that was not comfortable for me. I tend to-- If I'm going to worry about something, I'm going to choose to worry about money first. It was hard to talk together about making that choice, we made the choice together, and then we struggled to talk about all that was changing in our relationship as he was developing this whole new idea about how he wanted to work in the world and what life might look like for him. I really struggled.

I'm a journalist, so I thought, "Oh, if we work hard enough at this, and if we collect enough information and go to the couples counseling sessions and read all the relationship books, we are going to figure out how to tackle these tensions that became quite difficult." As I trace in the book, I think what I didn't really realize at the time, this was 10 years ago now, we were having really hard conversations that felt really sad and unsatisfactory because they didn't end with the solution.

What we were talking about was that we now wanted really different things and it took us a long time to just say that. Then, once that was said, "I want to travel all over the world and make movies. You want to have a house and kids, that's not what I want." Then we could look straight at it and say, "This isn't going to end in resolution." Now we have information and we can decide, "Let's move together or let's move forward apart," and that marriage ended.

Brian: Looking back on that moment beginning of the great recession, 2009, when you had these disparate goals in your lives that were becoming clear between you and your husband, with everything you now know from your book research on having hard conversations as well as just live for another 12 years and doing the work you do to help other people who are finding themselves in similar situations because those kinds of hard marriage conflicts come up all the time, would you have handled it differently if you knew everything now?

Anna: That's a good question, Brian, I thought about a lot as I was writing. The end of a marriage is always tough and sad because no one gets married thinking they're going to get divorced. What I do think would be different is I spent a lot of time just feeling like a failure because I couldn't figure out how to say the thing that was going to fix it. I think that that's often how all of us enter into hard conversations, "How do I make this person who is grieving feel better?" "How do I get around this awkwardness in this money conversation with my friend who I know is less financially stable than me? How do I ease that tension with words?"

The point of my book is you're not going to. You can't. Hard things are hard. If you go into a conversation thinking, "What am I not in control of resolving?" And instead meeting that person and saying, "What's going on with you?" "I'm going to tell you what's going on with me." Let's have this exchange of like personal intimate stuff and just saying out loud, "Oh gosh, this is different," your experience is different than me and not trying to smooth over those hard things instead sort of witnessing them together.

Brian: That was a money conflict as you just described it. I'm going to ask you about another thing in the money section of your book that's really interesting because you referenced money as both a symbol and a tool, and you go on to write, "We live in an era when tech billionaires wear jeans and sneakers, struggling people carry designer purses, and doctors and lawyers are drowning in student loan debt." You refer to some of this as, "Financial sleight of hand," what do you mean by that?

Anna: I think we all like to pretend that we're-- You can look at polls and even as the middle-class in the US has shrunk, if you look at income levels and who counts as being middle class, even as that needle has shrunk, people's self-identification in America as middle-class has not. There is this tendency to want to think of ourselves as like, "I'm like everybody else." What that sleight of hand does politically, interpersonally, is it papers over really big policy questions about how people are being affected differently and how money is working in our economy and society.

It also papers over, when you don't have a conversation, when you don't that just a little more space to admit when something is hard with money, either with a friend or a coworker, then you're preventing yourself from having that conversation that might actually help you with money. So much of figuring out how we manage our money now is on our own shoulders and what we are doing with our laptops late at night and our bank accounts. We need to be trading information. That's all lost when we just try to pretend we're all more or less alike when it comes to money.

Brian: Anna Sale listeners, you get the privilege now, the treat of being able to talk to Anna live on the radio because you can't do that on a pre-recorded podcast. Here we are. If you want to talk to Anna Sale, host of Death, Sex, & Money, and now author of the new book, Let's Talk About Hard Things, 646-435-7280, 646-435-7280. Maybe you want to tell a story of a good but difficult conversation that you've had on any of the five categories from her book, Death, Sex, & Money, plus she added family and identity. What do you think of when navigating hard conversations? What do you want to know from difficult conversations specialist, Anna Sale? 646-435-7280, 646-435-7280.

You might've also seen folks that she had a New York Times op-ed the other day, based on some of the research for the book. Let me ask you about that, Anna. You cited a Pew Research Center survey saying most Americans believe that people look out for themselves more than others, especially during the pandemic. What were you getting at?

Anna: Well, I was trying to get at-- This is not a thought that just I have written about, but the ways in which there's a crisis of interpersonal trust in this country, and alongside that is a crisis of loneliness. What I wanted to talk about in the essay in the New York Times was about small talk as this small sort of the way that you think about talking to people in your lives. Maybe people you are talking to and you haven't seen in your life for the last year or so just little signals that you can use to open up, "What's going on with you?" Maybe in a slightly deeper way.

These are real crises and each of us can play a role in trying to build back a little bit more strength of community, a little bit more strength of neighborhoods, a little bit more strength of relationships because we need it. We need it in America.

Brian: You just used the term small talk and the title of your Times op-ed is, "How To Make Your Small Talk Big." Go another step there?

Anna: Well, I wanted to say small talk is something everybody rolls their eyes at as if it's this surface-y thing that's meaningless but, of course, every conversation starts with small talk and small talk is how we can indicate to someone we're talking to that we care about them. It can be this opening. I'm not advocating for everybody going out on a street corner and saying like, "What's troubling you?" It's more about having that openness, perhaps being willing to be the first person who says something like, "I don't know. This has been really tough and I'm struggling." Then, to see what happens in that conversation.

Once you open up just a little bit further, then you're tending to that relationship. You're strengthening that relationship. You're pulling each other towards each other instead of being isolated from one another and that's important.

Brian: I was just going to ask you about the section of your book about identity. I'll just start and tease this a little bit because I think we have a great caller who can bring this up with you. You bring up the idea of sameness in the identity section to say, "Sometimes we pretend we're more similar than different." With that as prelude Janine in Springfield, Virginia you're on WNYC with Anna sale. Hi, Janine.

Janine: Hi, Brian. How's it going? Happy May.

Brian: To you.

Janine: I'm starstruck as usual with Anna Sale because she's amazing. I love listening to you.

Anna: Thanks.

Janine: I wanted to say, I'm still looking forward to your book. As I told the screener, I loved it when you said-- We were talking about your breakup and being able to-- I can relate to that because I went through a similar breakup and I'm very different racially than you. I'm a Black woman and the things that we all deal with as human beings, whether it'd be dealing with helping our parents who are getting older, dealing with debt, dealing with student loan debt, dealing with life in general, we are so focused on the general things that we do when terms of birthdays and the celebrations as human beings, but nobody wants to ever talk about the hard stuff.

I wonder if your book, and I think we share that as human beings. All of us, no matter-- As a Black woman and we're the same age, we have similar things that will happen to us as we go through our lifespan, yet the caste system that we exist in, in America sets us apart so much so that when a young Black man gets shot, the media immediately goes to what does the Black community think about, instead of thinking about what do we all as a community think about and how can we really have these hard conversations if you really can't even see our humanity and humanize one another?

In one way, identity is great because we need our identities in order to get over the caste system and does your book talk more about how the caste system actually affects us and keeping us separated so that we can deconstruct and have the conversation so that we can transform into some other system that is beyond caste where we respect our identities simultaneously respecting our similarities and the identities that we cling to in our identity groups?

Anna: A lot of people have written wonderful important things about this in America. Even that term caste system, I learned a lot from just reading the book Caste. What I tried to do in the book is bring those huge, big ideas down to the interpersonal, how these conversations are happening with people you work with, people you live with in terms of talking about identity with different genders if you're a couple of heterosexual relationship.

I try to identify why these conversations are so tricky and it's because when you say identity, what does that mean? That means both these large sweeping categories that were slotted into the caste system, as you say, were slotted into, and no matter how we personally identify-- Then you have this very individual and sense of identity. We're trying to talk about that all at once and you're having conversations across, having a conversation across someone who has experienced marginalization and what it is like to be othered with someone who has not had that experience. It can feel like you're describing being on the moon to a white woman, I would say.

What I try to tease out is let's think about how you are positioned in identity conversations, and then what your role is in the conversation. Is your role to be more of a listener? Is your role to say, "I don't want to have this conversation today. I have this conversation every day when I'm in an environment where I'm the only, and I can't do it today." And that's okay.

There's this wonderful line that I learned from a woman name Karena Montag, who does anti-racism training and restorative justice training out here in the East Bay. She told me she starts group sessions with the line, "Expect and accept a lack of closure." We are not getting together for this workshop that is going to fix this. If you come with that expectation, you're getting it wrong. Part of investigating how identity functions in America is looking closely and being open to that idea of, "This is not fixable through one set of conversations or through one set of bullet-pointed to-do list." This is something that is an awareness that we all have to move forward with.

Brian: Janine, thank you as always keep calling us. Another one on the identity section of your book Juana in Secaucus, you're on WNYC with Anna Sale. Hi, Juana.

Juana: Hi. How are you? Thank you so much, Brian, and Anna, I wish I had your book last week when I had a tough conversation with my family about separating in my marriage.

Anna: Oh, I'm sorry.

Juana: I was wondering, I think what hindered me from having that conversation was fear, fear of acceptance, fear of my children, and all these other factors. My question to you is culturally, how much of a factor is that in having this conversation? Because I think as a Hispanic woman, culturally, you are taught to not have any hard conversation, Death, Sex, & Money are like taboo conversations, nonetheless, love and divorce. I'm wondering, what is your take on culture, and what factor that plays in how you had these conversations?

Anna: Yes. I wrote about that because I was curious. I interviewed a guy who asked to be called Adrian, that's not his real name. He's a Filipino-American. He had the experience of having two really difficult miscarriages in his marriage soon after he'd gotten married. He was from this enormous big extended family, a Filipino American family, they were first-generation, they lived together when they first got here, very close, big family events all the time. It was a real crisis of like, "Who am I and where do I fit?" when he was in deep grief, and what his family would tell him, this family was Catholic, it was largely about going to church and that sort of thing.

The things they were saying were not comforting him, and it made him feel very apart at a time when he needed that family connection more than ever. He really struggled with it. He told me this beautiful thing that he eventually-- It took a long time, but for him, he realized that he needed to get some outside help. He got therapy, and he had this conversation with his mother later where he said, "I've been having a hard time. This is who I'm talking to about it, and this is what I'm finding helpful about it." It opened up this conversation between the two of them about her saying, "Look, I know that you are different than I am."

She grew up in the Philippines, moved to the US, he largely grew up in the US, and she said in the night, "I've always known you were going to be different than me because you grew up in this different context, and I love you, and I'm proud of you." It didn't fix that they moved through the world differently, but at least it allowed him to not feel that sense of distance and betrayal of his family sort of not fitting in his family system anymore. That's something that worked for him.

Other families are very different, but I found that to be a useful story because I think what I do write about a lot in the family chapter is something that is a common dynamic in family hardship is that question of, "How do we feel together? While also there's parts of me that are separate from you, and I feel pulled away and I also want to feel close." That's what happens to all of us in family. That is what growing up is. You pull away, you let go, and you also have this pullback to feeling close.

Again, if you go into the conversation thinking, "I don't need to fix that." That is what family is, but how can I find a way to relate to this person I love and hopefully find a way for them to be able to hear me. I think that's a good objective for family conversations. How did it go with your family?

Brian: Unfortunately, we don't have the time to hear a follow-up on that, but want to thank you for starting that thread of conversation with Anna as we run out of time in this segment. Anna Sale, the host of the WNYC Studios podcast Death, Sex & Money, is now the author of the book Let's Talk About Hard Things, which includes sections on death, sex, money, family, and identity. What can I say except if you want to read the part on sex, you're going to have to get the book because we didn't talk about it here.

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Anna: What a plug.

Brian: Let's Talk About Hard Things, Anna Sale's brand new book. Anna, thanks so much for sharing your wonderful thinking with us.

Anna: Thank you, Brian.

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