Death, Sex & Money's Anna Sale opens up about marrying young, how a senator helped repair her relationship, and discovering her "parent personality."

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Anna Sale

This week on We Are Family, Julia Dennison chats with Anna Sale, host and managing editor of the WNYC podcast, Death, Sex & Money, about marrying young, divorcing, finding love again, and figuring out what kind of parent she is.

Author of the book Let's Talk About Hard Things, Sale also shares the story of how a U.S. senator helped her ex-boyfriend become her now-husband.

"Alan Simpson, if you don't know who he is, he's just a guy who you just want to listen to talk," she says. "He's funny, there's just no one like him. And I get this call from him on my answering machine telling me to call him back, because he's gotten this letter and he has something important to talk to me about. And I'm like, what is this? And I learned the backstory when I called that [my ex] had written this letter and basically said, 'I know you don't know us. Here's the story. I'm a wildlife ecologist, spend time in Wyoming. My girlfriend, Anna, is a journalist in New York. I've spent too much time in the woods with the elk, and I'm asking you to call her on my behalf and ask her to come to this event in Wyoming.'"

Long story short? She wound up going to the event in Wyoming, married the ex, and now has two daughters with him.

Check out Episode 7 now for more with Anna Sale!

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Anna Sale: I'm Anna Sale, and to me, family is where you learn to love and be loved.

Julia Dennison: Hello and welcome to We Are Family. I'm here with Anna Sale, host and managing editor of the WNYC podcast, Death, Sex & Money, all about the big questions and hard choices that are often left out of polite conversation. Anna has covered politics for years, including New York City mayoral races and presidential campaigns. She's the author of the book, Let's Talk About Hard Things, and certainly parenting is full of hard things so we're glad to be talking to her. She has two daughters with her husband, Arthur Middleton. Anna, welcome to the show. Thanks for coming on.

Anna: Thank you for having me, Julia. I'm excited to be here.

Julia: Now, so you have two daughters. What are their names and how old are they?

Anna: June is 5 and Eve is 2-and-a-half.

Julia: June, I love that name. My daughter's 5 also, her name's Esme, but June was like... I was between June and Esme, so I've always loved that name.

Anna: Esme is a good name too. Is your child in kindergarten?

Julia: She's about to... Of course, by the time this airs, she'll have already been in kindergarten and be a kindergartener, which is blowing my mind a little bit.

Anna: Cool.

Julia: How about you? Are you navigating kindergarten?

Anna: Yeah, we just started kindergarten a week ago here in Berkeley, and my younger daughter just started going to preschool. So I'm alone in my house for the first time in a long, long-

Julia: Oh my goodness.

Anna: ... long, long time.

Julia: What's that feeling like?

Anna: I didn't know what to do with myself at first. I sat down in a chair and I turned on some classical music, because I was like, how do I mark this moment?

Julia: Right.

Anna: I sat down in a chair and just was like, OK. OK. It was... It's felt good so far. It's felt good. Yeah.

Julia: Good. So now this is a podcast about family, as well as parenting. So let's go back in time a little bit to when you were a kid. I'm going to throw a question at you that you wrote in your book, Let's Talk About Hard Things. One of those simple questions that can really open up a conversation. Tell me about your family.

Anna: That can be quite a can of worms, right? My family of origin, I grew up in a family of five daughters and I'm in the middle of the pack. And I feel like that really has shaped me in how I move through the world. We were a family of talkers, a family of feelings, talkers. And I think something that was really important for me growing up was my two older sisters are actually half sisters. We called them sisters growing up, but they are from my dad's first marriage and he got divorced and then married my mom. And so I had these older sisters who were younger than an aunt, but definitely older than peer. And so I grew up with this sense of having cool people to ask the biggest burning questions that weren't your parents, which I feel like was such a gift for learning how to navigate coming of age.

Julia: Right.

Anna: Oh my God. Thank God for my sisters. Yeah. And then my parents... I grew up in West Virginia, my parents were both in medicine. My dad was a doctor. My mom was a physical therapist. And yeah, I feel like for me, family, I was really, really blessed with this growing up feeling that family was a place of love. It was a place of a lot of different kinds of people, all fitting together in one unit. And yeah, it was a wonderful way to learn about family.

Julia: I love that. So did you feel like it was your sisters or your parents who would be the ones you turn to when you want to talk about Death, Sex & Money, since that's your topic.

Anna: Yeah, for sure, my sisters. My parents, we would talk, but it was like the way you talk to parents. I feel like my sisters were the ones who got the real dirt, and would give me the real dirt. We were raised Unitarian Universalist, so that was also something that was really important to me growing up in this community of where the idea that it's important to think about big questions and values and have some principles that guide your life, but also that there's more than one way and that's OK. So I really credit my parents for setting that template for our family culture. But for sure, when it was questions about sex or drugs I went to my sisters and not my parents.

Julia: But also in your book, you talk about how you can get trapped in an idea of identity within your families. You have these tropes that we all talk about, I don't know, like goofy, younger brother or anxious mom. What have some of your own family identities been, and how about your own identity within your family? And how do you shrug those off if it's not something you want to take through your life?

Anna: I would say I've definitely shrugged them off in relationships outside of my family, but I totally revert when my family unit is back together. That's the thing about these family roles, even when you feel like they're ill-fitting or you've outgrown them, they're still there. They're like a suit that doesn't quite fit, but that you still zip on. As I said, my family was a big family of talkers. And even though I'm a professional communicator now in my work as a journalist, I noticed that I'm not the one leading the conversation when I'm with my family, I'm much more the listener and observer.

And I think also, my sisters would say about me, I am like a very classic middle child in that, Anna growing up was always about being independent, accumulating a lot of trophies, and being pretty achievement-oriented. And also learning how to play both sides, which I feel middle children are very adept at, which I mean that I would change alliances on road trips depending on what would work better for me. You can think of that as being diplomatic. You can also think of that as being highly manipulative and adaptable, but I think both apply for me. Yeah.

Julia: I wanted to move on and talk a little bit about your own relationships. I've been divorced, and I know you have too, and I wondered if you could talk a little bit about your first marriage, it was short lived, and it ended... You were blindsided, it seems like, or it ended when you were... It was devastating and confusing, you said. You didn't really know what had gone on. Can you talk a little bit about that and how you processed it?

Anna: Yeah. Yeah. First shout out to the divorcees who are listening. I remember when I did finally make the decision to end that marriage, I was like, OK, I'm just going to own being a divorcee and just really try to build out that part of my identity, because that seems really sexy and cool.

Julia: I love that, divorcee. I remember I had a moment too where I was like, OK, I'm going to own that. It's so sophisticated sounding, so let's go with it. But yes, I love that. Go on.

Anna: Yeah. So, now I consider myself both a wife and a divorcee because I'm remarried, but I still think having gone through a divorce was really, for me, a really pivotal time in just how I thought about life, how I thought about mistakes, how I thought about growth, certainty, stability, et cetera. And as you described, for me, I first got married when I was 26 to... My ex was someone that I met when I was still in college. We were best friends. We became adults together through our twenties as we dated.

Julia: Same. Same. Same.

Anna: Yeah. And so it was this feeling of like, oh, I have found my person and now I'm going to—alongside this person—I'm going to build this life for the rest of my life. Thank God I have figured out this one big mystery question about who's going to be my person, I had found it. And then we started to have trouble, and it started with small things where you're like, oh, is this... Are we arguing more frequently? Or like, what is this about? And can we talk this through? And it just became an accumulation of small fights that then led to the recognition over time that this wasn't about just us not having communication skills to work through conflict. This was about us really fundamentally wanting different things. And the way I experienced that was it was a real shock, because the first feeling I had was just failure, this is not who I am.

I am someone who makes a commitment and who cares about family and will make my marriage work. And when that wasn't working, I had to update that sense of myself. And that was really a painful process of letting go of this idea of what our marriage was supposed to be. And I think once I did that, and we did that together, beginning at... We were in couples counseling and read all the books together, and then finally decided together that this was the right step for us to take. And once we did decide to end our marriage, I think both of us just felt this immense sense of relief of like, oh, OK, we get to ask for this. We get to ask for this difference, and to let each other go.

But for me it was this... I just had to... I had to let go of this idea of what life was going to be. And it wasn't what I expected. It's not... Most people get married with the idea that they're going to stay married. And so for most of us who get divorced, it's not something you anticipated. So that shock takes some time to process.

Julia: Yeah. Your whole personal identity that you have as a person. And yeah, and just like dealing with that whole shift, and what you expected to have happen. And what actually is the reality and acceptance and everything. It's a lot, it's a lot to process. But you met your husband pretty soon after you'd separated from your first husband, right? How did you know that he was the one?

Anna: Oh, well, I met him very quickly and I knew I was very attracted to him and that he was someone I wanted to spend time with. So we did that. And then it was two years of being angsty about whether I was ready for a relationship.

Julia: Of course.

Anna: Because I wasn't ready for a relationship. I had a lot of healing, and for me, also just figuring out how to trust that I could stand on my own two feet. And I wasn't just falling into the arms of a man who was going to make me feel safe again. I didn't really trust my motivations. And so that was the backdrop of our early romance, because I did meet Arthur... My divorce wasn't final yet—it was filed, but it wasn't final.

So, I was in very much a state of upheaval when we met. But it was hard for both of us because we were long distance, and I think being long distance was really important, because I did still get to have that space of like living on my own, feeling like I was making my own decisions every day about, I don't know... What to do after work and not having to negotiate that with a partner.

And then the question became for me, it was like, I was now in my early thirties, I knew I wanted to be a parent. So there was this sense of time pressure to like, OK, are we doing this? Are we not doing this? Because if we're not doing this, I need to make some other moves. And so it was a lot of pressure.

It was not smooth. We broke up once and then we quickly got back together, and then we broke up again and then it really felt like it was for keeps. And then Arthur realized he didn't want to break up. He swung hard and was like, "It's OK that we don't know what our life is going to look like together, but here's why I think we should do it together."

That helped me. I think it was divorce fear. I really felt like if I couldn't visualize how our life was going to work together, I was afraid to make that commitment. But seeing how Arthur rose to the moment and just... He is someone who is extremely adept at talking through feelings. And it made me feel comfortable in the idea of like, oh, this is somebody who I can figure out things alongside, and we don't have to have it all baked in before we decide to take this next step.

Julia: Yeah. I think it's interesting, because I think there's divorce fear, but I feel like... I also say divorce is a superpower too, going into... I hope—at least I like to think so—going into new relationships, because you're really careful about what you want, and how communication like that is so important. I have a question though. So how on Earth... I read that Senator Alan Simpson got involved in getting you guys back together. Can you talk about that story?

Anna: Yeah, I was like, should I say that now? It makes it go off this whole other tangent when I introduce that weird detail. But yeah, so during that period of where we were really broken up and I really thought we were done, I was supposed to be Arthur's date at this event in Wyoming where he was getting an award for some research he was going to do; he's a wildlife ecologist. So that was on the books. And then we broke up and I was like, "Look, I'm not going to come to Wyoming, to this event. I think that's best." And he had this idea, he was like, I think if Alan Simpson, the former senator of Wyoming calls Anna, and asks her to just come out to this thing in Wyoming, I think it'll make Anna laugh.

Julia: It's like your equivalent of the boombox outside the window.

Anna: Exactly. Yeah. Which is like... It totally is, which I loved that movie as a teenager.

Julia: Yes, me too.

Anna: So Lloyd Dobler, love him. And so it did make me laugh and it was also just so specific to, I don't know, me and the things that I would be delighted by. Because Alan Simpson, if you don't know who he is, he's just a guy who you just want to listen to talk. He's funny, there's just no one like him. And I get this call from him on my answering machine telling me to call him back, because he's gotten this letter and he has something important to talk to me about. And I'm like, what is this? And I learned the backstory when I called that Arthur had written this letter and basically said, "I know you don't know us. Here's the story. I'm a wildlife ecologist, spend time in Wyoming. My girlfriend, Anna, is a journalist in New York. I've spent too much time in the woods with the elk, and I'm asking you to call her on my behalf and ask her to come to this event in Wyoming."

Julia: So now Arthur and you got married, and now obviously we're here at Parents, so we love to talk about parenthood. What was your journey to motherhood and parenthood like?

Anna: Well, it was like... I was very, very lucky because we got married in August and then our daughter, June, was born in June the next year. So I went off birth control right around the time, right before our wedding and then promptly got pregnant, and I was like, oh, OK, so we're doing this. So that was that journey that was like, we're moving into this next phase.

Julia: Yeah. So that was easy for you. That was an easy journey into motherhood for you.

Anna: That was easy.

Julia: But of course it's like… It's all well and good that it's easy, but then of course motherhood and becoming a mother is a huge identity shift. And you talk a lot about identity and family, and I'm just curious to know how, one, the journey and then also going through your pregnancy, and how that impacted your idea of self.

Anna: Oh my gosh. In so many ways. I feel really lucky that it wasn't hard for me to get pregnant that first time. And that was just such a blessing. And I know it's not something everybody gets to have come easily. And then my pregnancy was mostly OK. There was one very weird curveball, that a late ultrasound found that I actually had like two placentas. And my baby's umbilical cord was connected to the junior placenta or the baby placenta called an accessory placenta. So that was a weird thing. And then she was breech so I had to like, OK, I guess what childbirth is going to look like isn't what my childbirth class in this Brooklyn yoga studio has prepared me for. I ended up having a scheduled C-section.

By that point, once we were coming into the end of the third trimester, I was pretty detached from what the birth process was going to look like for me, because I just wanted to see this child and make sure she was safe. And it was really troubling to me during the last phases of pregnancy when you could feel this giant baby, but couldn't just see her to check on her. I was very excited to just have the baby out of my body.

And, I don't know... How has that changed me? So many ways. I feel like there's parts of me that are just more. But I don't feel like, for me, I've had a lot of parts that I've had to really let go of. But I feel like as a parent, I just feel like my life is full, like fuller.

And certainly I guess... I think that having a second child, I think, ramped it up even more because that made the way that I move through the world, and the way that our family routines work—they're pretty prescribed. So I think the one big thing I had to let go of was flexibility and spontaneity which I miss, and will someday hopefully get a little bit more back into my life, but it's really fun. It's really fun to get to know these people who've just shown up.

Julia: Yes, absolutely, with their own individual personalities and everything that like... So often as a parent, I just think that... I would always think that I would know what to expect when it came from my daughter's personality, and then you find out that they're their own humans with their own ways of being, and it's quite remarkable. That sounds obvious, but it is a thing that dawns on you. So you talked about the uncertainty around the time that you're developing what you called your parent personality—you just don't know what parent you're going to be until you are one. What mom do you think that you turned out to be? And what about Arthur? What kind of dad is he?

Anna: Those are big questions. I feel... One thing that I have observed is that I am like, "Huh, this is interesting." I'm a parent who is pretty comfortable letting my kids do almost probably, basically crossing the line into dangerous things on the playground, which I think is like, when you observe-

Julia: Free range, we'll call it free range.

Anna: Yeah. Your relationship to risk, I think as a parent, is something that is interesting to notice. Arthur has a similar thing of just like, "We'll take the kids down in a raft, down the river, put them both in life jackets and try that out." Or, we spend a lot of time outside and exploring outside and climbing trees. And so I think that that has informed an exploring and adventuring spirit.

So yeah, I don't really think I can tell you what kind of mother I am, because I feel like it just keeps changing. And I feel like it's something more that you notice-

Julia: Of course.

Anna: ... than what I'm intentional about necessarily. I feel it's what causes me extreme anxiety. I notice things like, I get really freaked out when it's wildfire season out here. I had a really hard time thinking about earthquakes, and the earthquake risk every night going to bed every night once I became a mother. It was like, I've had to work on how not to just have catastrophic thinking right before I go to bed. But things like my 5-year-old hanging by her knees from the really high monkey bars, I'm like, it's cool. She's cool. She wants to try that. Yeah.

Julia: Yeah, no, absolutely. And so obviously like your podcast is Death, Sex & Money talking about these big topics. Have you put much thought... And your daughters are still super young, but 5-year-olds ask crazy questions. I know this because I have one. Have you thought about how you're going to approach those bigger topics with your kids, and have you had any conversations yet with June about those really big topics at all?

Anna: Yeah. We have. I think the one that asserts itself, whether you like it or not, is death. For us, we were lucky that her first encounter with death was the tarantula, Sparkles, in her preschool class. So that became... She got to practice the rituals of death and remembering with Sparkles. But it was not long after Sparkles died when they buried the memory box, and they talked about how they would remember Sparkles, and then somebody very close to us lost her father. And so we had that template of like, so she's very sad right now because her father died. And so she's thinking about how she's going to remember her father, and these are the things that she's doing to help honor her father. And so we use the word dead a lot, whether it's everything from a person to a bug, just introducing this idea that death exists.

And sex, we haven't really gotten into the real meat of sex yet, but something that I... I interviewed a sex educator once, and I thought about this a lot. She worked with communities of people with disabilities and talked a lot about how they could assert their own agency around how they... What was a private thing for them and a private part of their body versus not private part of their body. And you think of how to... Giving people words for that in the context of being cared for. And she went on to describe how she had used that template for her kids when they were really little. And with kids, you've got to talk about body stuff really early on, as soon as the potty training starts. You have to explain these very basic ideas of like, "These are private parts of our body. This is private. We don't do this in public." And this idea of these private parts of ourselves, we share them with people... The only people who we trust, we share it, you get to choose this.

So you're creating this template for consent even though not talking about sex, but we're talking about bodily autonomy, and I hope to build on that. And for us, where babies come from and how they get there, we haven't fully closed the circle, but they know... One thing that's cool is like, my daughter June knows that my C-section scar is where she was born. And then my other daughter, Eve, who I had a VBAC, she knows she came out of another part of my body. So we talk about that. But that's the building blocks that we're working with right now.

Julia: I love that. And I think it's so important to be frank and honest with our kids. That seems to be the move... The direction of travel when it comes to parenting. But even Mr. Rogers used to talk about death so frankly and matter of fact, and just not... Kids are aware of more than we often give them credit for. So I think that's really cool that you guys are so honest about that. So we always end the podcast asking people about their hopes for the future of their family. And it seems like your family has a pretty adventurous spirit. What's one adventure that you're looking forward to having together as a family?

Anna: Oh, this is very specific, but I want to tell you all about it, because if you don't know it exists, think about it. Something that got introduced to my life when I met Arthur who does a lot of field work in the areas around Yellowstone, are just the wonder of being in the back country, and really being far away. And before we had kids, and only once since, we would go... He did a lot of work by horseback. And so I went on a few pack trips with him. And a pack trip means you go up into the mountains, and you're on a horse and mules carry the load for the campsite on their backs so they follow behind you. And you can go with a guide, you can go without a guide, but I think about being able to take our kids on a pack trip. And how excited I am for that, just seeing them in these vast landscapes where you are... It's you, and the mountains, and the sky, and all the animals around you, including some animals that are like grizzly bears that can be scary. And you get to feel what it feels like to be a part of nature, and not just trouncing all over nature. I think about being able to do that with them, and I'm very, very excited. The word is in Wyoming, you, you want to wait until your child is old enough that they won't just fall asleep when they're rocking back and forth riding a horse.

Julia: Oh, OK, that's-

Anna: So, I think we're a few years away. Yeah. It's a good tip.

Julia: That's a very good tangible tip.

Thank you for coming on to We Are Family. We are so happy to have you. It's been great to chat, so take care and love to your family. Thanks for coming on.

Anna: Thank you, Julia. Thanks for having me.

Julia: Thanks so much for listening to my conversation with Anna Sale. Her book, Let's Talk About Hard Things, is out now.

Come back next week when we will be talking to award-winning journalist, author, and broadcaster Tamron Hall about the devastating impact on her family of her sister's murder and her journey to motherhood via IVF.

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We Are Family is presented by me, Julia Dennison, and produced by Sam Walker. Editing is by Vincent Cacchione, and thanks also to the rest of our production team at Pod People, Rachel King, Matt Sav, and Danielle Roth.

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