“One of the big messages of the book that I hope people allow in is: some hard conversations are hard because you’re uncovering a truth that you’re not quite ready to face.” Journalist and host of the WNYC podcast Death, Sex & Money Anna Sale talks with Zibby about the hard conversations she had to have to write this book and how they feel different from the ones she’s been having throughout her entire career.


Zibby Owens: Welcome, Anna. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss Let’s Talk About Hard Things.

Anna Sale: Thanks for having me.

Zibby: This is the best title ever. It’s the best concept for a book, the way that you divided it into sections. This is what I love doing, is talking about hard things. It’s perfect. It’s just perfect.

Anna: Excellent.

Zibby: I should’ve actually used this as my podcast name. It would’ve been much better. First of all, why don’t you tell everybody what this book is actually about and then how you decided to do it and how it came out as an outgrowth of “Death, Sex, & Money” and your podcast and all of this good stuff?

Anna: The book, Let’s Talk About Hard Things, it’s kind of a lot of things. It’s a memoir, in part, mostly focused on what happened in my life when I was at the end of my twenties starting my thirties. My first marriage was ending. It surprised me. I was not expecting it. It felt like I was hit by a freight train, and then had to figure out how to build back the emotional scaffolding to help me figure out the next phase of my life. The way I did that in my life was by just talking to anyone who would talk to me about how they did life, relationship of people in their lives, particularly with women, career choices and where to be and how to make it work. I wanted to be a mother. All of a sudden, I was divorced. I was in a relationship with this guy who lived in Wyoming. What? How is this all going to work? That’s what led to me starting the podcast, “Death, Sex, & Money.” I found myself so fed by these conversations in my personal life that just acknowledged that all of us have these messy, uncertain moments. I wanted to hear more of that. I covered new and politics for a long time for public radio. I just wanted to be doing journalism that was of a more personal quality but still equally urgent. I needed this in my life.

That’s how we started the podcast in 2014. The show’s now almost seven years old. I found that people would ask me, wow, how do you talk to people about such private things? How do you get people to open up? I found that I would kind of describe my intuitive process. Well, I just am curious. I ask. Then I listen. I found, oh, I would like to reflect on this more. How can you set yourself up to have a more successful conversation about hard stuff? There is a skillfulness to it, to both manage the timing, and how do you create the particular space? Then how do you know when you’ve said enough and you can revisit it? That all led me to think about the book, which was how to apply what I do in a radio studio to conversations in real life. I wanted to look at what I had learned. Then I also interviewed a bunch of people, more than thirty people, for the five chapters, which are Death, Sex, Money, Family, and Identity, just honing in on these moments of critical conversations in their lives to see what they would add, what wisdom they had to share.

Zibby: Wow. It turned out great. I, of course, liked — I shouldn’t say of course. I loved the interviews you did and all of the great information, but my favorite parts were about you. I really just wanted to hear more about you and the way that you’ve gotten through the hard things in your life. I loved how you started with your divorce, your unexpected singleness at thirty, and how your life just took a different path and then how you tracked the evolution until you understood what it was that made the relationship end. Then it all comes full circle when you’re like, maybe one of us changed. Maybe he changed. Maybe we didn’t want the same things. It was just such a great arc of you. I feel like as a reader, you’re so invested. I found myself — this is now sounding creepy. I’m like, ooh, what does she say about her in this chapter? It gives such a context of everything else.

Anna: Thank you. When I think about the whole arc of that experience for me and when I think about how I talk to other people about hard things, for me, going through that phase of just rebuilding my life and how I felt about it and reading it now, I’m like, oh, you just had so much shame and feeling like you messed up instead of being able to look at what I finally saw. It was a natural end to a relationship. We had loved each other. Then we looked up and realized the life that we want — I want something very different than you want. We had to battle about that and argue about who was right for a while. Then we finally just let it be okay that we wanted different things. It was a real blow to my identity because I thought of myself first as someone who is a really hard worker. If something is not working, I’m going to harness the resources to make it all better. I’m going to read the books. I’m going to go to the counseling. I’m going to do the thing. One of the big messages of the book that I hope people allow in is some hard conversations are hard because you’re uncovering a truth that you’re not quite ready to face. It doesn’t mean that you’re not good at having a hard conversation. It means that you are uncovering something hard and maybe sad. That was probably a good conversation to have. Now you know, so you’re not in denial of it.

Zibby: It’s so true. I feel like often people say you have to be so brave to talk about things, but it doesn’t feel like bravery. You just have to feel like you’re not going to be made fun of or that the other person actually cares.

Anna: I think that does take a certain assuredness to be okay being vulnerable. When you name the hard thing, at least you’re not faking it. I tend to come down on that side. I may look foolish trying to have this conversation, but I’m really trying to name a thing that I think is there and we’re pretending is not there.

Zibby: I’ve found that often people don’t mind being asked more and more about themselves. People don’t usually mind. I try to couch it like, if you don’t want to talk about it, that’s totally fine, but most of the time people are happy to talk about hard things about themselves, maybe not the hardest.

Anna: It takes listening and waiting for ques. Maybe they’re not ready to talk about that aspect, especially in some public forum. Maybe it’s private. I agree with you. By and large, if someone has been through something and learned something as a result of it, if you are opening up an opportunity to say, tell me, what was that like? they want to share.

Zibby: Anna, what have you been through lately that you found hard?

Anna: Oh, my goodness. I have a four-and-a-half-year-old, she’s almost five, and a two-and-a-half-year-old. The two-and-a-half-year-old, we’re really trying to get potty training nailed down. I’m working from home. I’m forty. I think the hard things right now for me in my life are just the post-pandemic visioning and trying to allow myself to maybe want some things to look different without being really afraid. That sounds very abstract. I find, as that person who likes to read all the books and go to the counseling and figure everything out, to really try to just be open to, huh, what could shift here? comes with a lot of anxiety. That’s the hard thing that I’m in right now.

Zibby: I totally agree. It seems very unclear. Things seem unclear how much they’re going back to normal and how much they’re not, and then the people who are more comfortable with certain things and then people who are not, and friends and kids.

Anna: And we’re all doing it at the same time. Usually, we’re a little staggered at who’s on top of their game. We’re all just, ah!

Zibby: It’s true. I know. I went to the park the other day. This is now maybe three weeks ago or something. It was one of my first times back in Central Park. The friend I met, and her daughter, to meet my daughter and me, my seven-year-old, they weren’t wearing masks. I was like, but I feel still like I need to wear a mask outside. I want my kids to wear masks. Then of course when my daughter saw her daughter not wearing a mask, she ripped hers right off and was like, “She’s not wearing a –” I was like, oh, my gosh, here we go. Not that this is so hard, but it’s just like, okay, parenting through post-pandemic, where’s the rulebook?

Anna: It is hard.

Zibby: What do you do when your friends disagree? Potty training in general, by the way, is really not fun, obviously, but I bet now it’s even worse. I started bringing Tupperware in the car so that we wouldn’t have to go a public bathroom in the pandemic. Now the kids don’t want to go back to the bathroom stops. I’m like, no, no, no, it’s time to put the Tupperware away. Oh, my goodness. Let me just ask you about your podcast. Seven years of a podcast, so much, obviously, has changed in seven years. I didn’t even know what podcasts were seven years ago. I barely knew what they were three years ago when I started mine. You’ve seen this whole evolution shift. Has it made you change anything in the way you do your prep, your show, your anything, the way you approach it, the way you think about it? Has anything in your process shifted with the growth and popularity of the medium and also the show and all of that?

Anna: I do feel like as it’s expanded in the universe of what feels possible with the ambition to make a podcast and cultural impact you can have, it’s like, whoa, this is such an open, wild frontier. It’s changing so fast. When I started my show, I was at WNYC. It kind of felt like it was the JV squad. They’re like, sure, we’ll let you try to have a podcast. See what happens over there. Then I realized I really prefer this to broadcast radio because you can create this sense of community. You know. When people are opting in to listen and join in and be a part of a conversation, the sense of connection that you have with your listeners and what they’ll share with you is incredible. You can just continually experiment with format. What kind of sound do we want to use? How graphic do want to get in the — it’s just a really fun space. I feel like now I just have to remember — it used to be there were so many fewer podcasts. It was easy to sound original. Now it’s more like trying to find peace with, podcasting is like cable television. These are my buddies who I think we would end up on HGTV together. I can learn from them. Wait, what’s happening over there on ESPN? What would be an interesting — it’s just continually being surprised and inspired by the landscape, is how I think of it now. It’s amazing how much is being made.

Zibby: Did you have trouble with the book adding the two extra categories? Did you debate which ones those would be?

Anna: I actually looked back at the book proposal. It was originally supposed to be eleven chapters like work and friendship and teasing out more stuff. Then I realized, that’s going to be an encyclopedia.

Zibby: Part two. Two book-deal, what’s going on?

Anna: Then I thought, should we just do death, sex, and money in the book? I kind of wanted to pull out family and identity and add those because I think they added an important dimension. They are real sources of hard things. To just ignore that or flatten it, I was curious what I would learn if I said, okay, what is hard about being — it’s primarily about being an adult in a family and what your relationship is to your family of origin and what tensions are built in to just what’s part of growing up and growing apart and also what happens when there’s real differences in your values and how you see the world. How do you navigate that? Identity, I just really wanted to include because I feel like that’s where I have felt the most, I’m just going to stop talking because I’m afraid I’m going to say the wrong thing. As a white woman in particular who’s financially comfortable and doesn’t have a disability and has been a citizen of the United States, there’s so many ways I’m aware that I am not competent and have not been competent. Rather than just pretend that I don’t feel those things, I was like, let’s dig in and see. That’s how I came to the five. Honestly, when I think about over the seven years of the show, family and identity have also woven through “Death, Sex, and Money” in different dimensions too, so it felt pretty natural.

Zibby: I felt like your whole section on death, it’s a very good time, essentially, to give people the tools that they need because it’s hard to ignore it. It’s one thing if you’re busy in your life and one friend has something happen, but this is so universal right now that giving people these skills is the baseline for discussion. There are other books and guides and things to what you should do to be a good friend talking about death or what you can do. When you were doing all your research, what was new and surprising to you in it?

Anna: I just really loved being reminded by this woman Megan Devine who’s a grief counselor, don’t say everything happens for a reason. Don’t say, what can I do to help? Don’t say the things that you just try to say to show yourself to be useful. Instead, really try to say the thing that says, I see you’re in pain. I love you. I want to tell you it’s okay that you’re in pain or you’re angry, or whatever the sets of emotions are for someone in grief. I also wanted to explore talking about death outside of the context of terminal illness. I love people in my life who are older. I think about their death. I would feel bad about thinking about their death and was like, should we talk about their death? What should I do here? One conversation I forced myself to have in the course of writing it was sitting down with my friend Ann who’s now in her late eighties and just saying, what is it like for you? How do you think about this? How have you tried to be a friend to people who are seeing parts of themselves diminish with age? What did you learn from being the friend and the caregiver in that situation? How do you notice now when people are trying to do that with you? She just said one of the most simplest things. “I noticed when I would walk alongside someone who is older, I would offer my arm. Sometimes they would just take it wordlessly. Sometimes they would kind of shrug it off.” We were in that interview. Just a few months later, we were somewhere out in public. Ann Simpson is a proud, dignified, cool woman. She’s in control. We were walking. I just offered her my arm. We had to walk through this corridor while we were both going to the restroom. It was really special that she had shown me how to show that kind of care without making her feel uncomfortable or bothered in a way that made her feel a way that she didn’t like.

Zibby: My grandmother just passed away at ninety-seven. Until the end, I’d be like, “Here, let me help you.” “Get away.” She was hilarious. To the last second, she’s like, “I can do this myself.” Then I was thinking, I’m like that too. What makes me think that when I’m older I’m going to let people do things? No matter what happens — I bet you are the same way, but maybe not. C-sections or whatever, I didn’t want any help. I’m good. I don’t know. Just assuming older people would want that, it’s tough for independent people who are used to that, such a shift. I love, by the way, in the book how you were explaining when you had this conversation, all the things that the person who is experiencing grief has to then process when someone just says, let me know what you need. It’s not just that. I have to figure out what I need, which is hard in and of itself when I can’t even get dressed in the morning or whatever. I have to figure out what I need. I have figure out which of my friends can give it to me. I have to ask that friend. Then I have to deal with the fact that that friend might say no. Then where am I left? Now I’ve wasted all this time and energy. I think it’s just so useful how you painted that whole picture of what happens and the pitfalls.

Anna: The other thing I love about that story with Megan is when she talks about her friend who was really worried about her, who needed assurance that Megan was going to be safe. She’d just lost her partner suddenly.

Zibby: Oh, yeah, with the texting. That was so sweet.

Anna: We don’t have to talk, but I just need to know you’re okay. They had a system where Megan would just text her in asterisks, like, I’m here. If we could all say, I’m worried about you, and instead of imposing work on you because I’m worried about you, can we figure out a system? I thought that was really moving.

Zibby: I loved that. That was really great. What was it like for you doing this book? How long did it take? What was your process like? Did you enjoy it?

Anna: It was really hard. I don’t know when I thought I was going to write when I agreed. I was like, oh, a book proposal’s fun to write. Ideas, I love this, a whole new way of communicating. That’s going to be so fun. I had one child when I signed the book deal. Then I had a second while I was writing. It was hard. I also had a job. I took vacation time to do reporting trips. I used part of my maternity leave for the second kid. I had some childcare. I did a lot of writing during that phase. I think if someone had told me, writing a book for you is going to be like going to college, it’s going to take four years — I wish someone had told me that. From signing to now the book coming out has been four years. If someone had told me, that’s okay, you can expect that, you can expect all the emotions that you went through in college, then I would have felt a lot better.

Instead, the hardest part for me about the book was it was a thing that was never done right here in the back of my head while I was doing my other work, while I was trying to be with my family. That was a new kind of work for me. What’s been so satisfying about working in newsrooms and making a weekly podcast is you get excited about something, you make it, and then you share it. It’s out there. This was something that I was carrying for a long time. I’m glad in some ways because I got to just really mull over this stuff. What do you have to say, Anna Sale, about death, sex, and money that’s not been said by every religion in the world and every book of literature in the world? What is this adding? I got to think about that a long time. The thinking about it for so long was tough, but I’m very glad I now have a book I can hold in my hand. That feels satisfying.

Zibby: That’s excellent. If you were to do another book — first of all, maybe you are doing another book. Let me change this. Are you doing another book?

Anna: I’m intrigued by another book. I do think what was really fun about this book, I like the mix of, this is something I’ve gone through, and then doing reported interviews to add different dimensions to it. I think that’s a really cool forum because you can both go inward and also do this really broad survey. That’s why I make of money the way I do, because I like that. I’ve gotten really interested in children’s books and how we tell stories to our kids about how the world is. The conversations you can have with a four-and-a-half-year-old really make you think about, if I really want to break this down, in a way. It’s a real challenge. I think about both those things. I’m interested.

Zibby: Cool. That sounds good. I’m also interested.

Anna: I’m also interested in perimenopause and menopause as a forty-year-old. I feel like every person I talk to who is slightly older than me, they’re like, this is what’s coming, and no one talks about it.

Zibby: Literally, I feel like I’m in Disney World or something and I have just put the contraption on and I’m holding onto the sides. Everybody’s waving at me. I’m just sitting there waving back waiting. I sweat at night. That’s my only thing. Otherwise, I’m just like, I don’t know, I don’t think this is it. We’ll see.

Anna: I love that idea. You’re like, uh…

Zibby: I don’t know. Here we go. In truth, that’s really with everything. We don’t know what’s coming. Who knows what’s coming next? There are people who make you fear it and people who embolden you to go forth. It’s going to be okay. It’s going to all be fine. It’s going to be what it is, or it won’t. Then we just pick up and move on. That’s sort of what we have to do.

Anna: You have to go through it.

Zibby: Just have to go through it. What advice would you have for aspiring authors?

Anna: Something that I loved about writing this book was that it forced me to make space to write, which can be really hard when you have a job and kids and a partner and life. Being like, no, no, this is my Saturday morning, you have to take the kids to the playground, I’m just going to sit and stare at this blank page and say, what’s this thing that I haven’t given words to yet? I loved being forced to make that space. My advice to aspiring authors is you just have to build in those slots of time. Maybe you won’t be productive, but it’s just to see what’s stirring around in there. Give yourself that time. I know moms don’t have time like I didn’t have time. To be really forced to be like, no, just take a little bit of time that’s protected from other things because this is important, that was a gift of writing this, of being forced to take that time. Otherwise, I would’ve just filled it with other things.

Zibby: I love that advice. I’ve been trying to work on something. I found the only time I can reliably do it is if I sit on the last kid’s bed who’s yet to fall asleep. In this case, it’s usually my almost-fourteen-year-old daughter. I sit on her little bed with my laptop. I’m like, you just go to sleep. Just, shh. It’s before I go down and talk to my husband again and deal with my emails and whatever. I read while the little guys fall asleep. Then I write while she falls asleep. At least it’s a little bit.

Anna: Also, thinking about that that’s going to be a memory of your daughter’s, looking at the foot of her bed and seeing you, that’s cool that she knows, this is how my mom made space. She fit us all around it. I like that.

Zibby: This has been so nice. Thank you so much for coming on. I really appreciate your time. Anytime you want to talk about hard things, give me a call. I’m always up for talking about hard things.

Anna: Thank you so much. Thanks for having me on. Thanks for creating the communities you have. They’re really great. They’re amazing.

Zibby: Awesome. Thank you. Bye.

Anna: Bye.



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