The Sunday Magazine

Death, Sex & Money host Anna Sale on how to have better conversations

The creator and host of the podcast Death, Sex and Money brings her trade-mark deep empathy to the page in her new book, Let's Talk About Hard Things. Anna Sale joins The Sunday Magazine host Piya Chattopadhyay to discuss how to nurture your relationships with words, and why we need to give each other space to fall apart sometimes.

'The skill is to be comfortable in that space of a lack of resolution,' says podcast host

Podcast host and author Anna Sale says we need to embrace uncomfortable conversations. (Simon & Schuster)

How are you doing...really? If your days are full of soft pants and surface-level conversations, Anna Sale wants you to push through.

"If you really go into [a conversational] with a spirit of, 'I want to say what I think but I also want to come away with an understanding of what the person I'm talking to thinks about what I'm saying,' it just changes the quality of the exchange," she told The Sunday Magazine's Piya Chattopadhyay.

Sale hosts the podcast Death, Sex and Money where she often discusses what's left out of polite conversation. In her new book, Let's Talk About Hard Things, she aims to guide readers through those tougher moments in order to have more honest communication.

She spoke with The Sunday Magazine's Piya Chattopadhyay about navigating challenging conversations. Here is part of their conversation.

How are you?

I am okay. I think like most people in the United States and in Canada, I feel like I'm in transition to something that I don't know what's coming next. So I'm unsettled in that way, but I'm okay.

What do you think of that question as an opening salvo? It's mostly used this way as ... that dismissive or fleeting thing, where I'm just doing niceties.

I think I learned in college at some point that small talk can be akin to, like, grooming in primates. And I kind of think … it's a way of saying, "I care about you. I'm not really asking for any information, but I care about you."

So I kind of think, "How are you" functions in that way. I just tend to have a personality where I'm always going to try to give an honest answer.

So the hard stuff — you know, death, sex and money, identity, family — the things you talk about all the time. You say it's more important than ever that people have these conversations.

It used to be that there were sort of scripts, whether it's through institutions saying, "This is how you ought to live. And this is what you ought to do when something happens." 

And now I feel ... the way I manage money, it's me and my computer figuring [it] out with personal finance blogs. It's very isolated. As our society has changed, I think more of the burden of doing the problem solving and making these choices is happening at an individual level. 

So I think that there's even more of an imperative that we talk about this stuff between each other interpersonally because we are each figuring it out with fewer guides with fewer road maps. 

And so it's a reason to sort of push yourself into those uncomfortable conversations. Because what we're each doing is hard. It's hard to write your own script, and you don't have to do it by yourself. You can compare notes through these kinds of conversations.

Can you listen to me? Can you allow me to be different from you? Can we come together around the things that we both value? That's what's happening when you're talking about hard things with someone.- Anna Sale

So I want to ask you about a couple of examples that you write about in your book. And the first one is about this woman whose husband died right in front of her. She's actually a grief therapist, and something that you learn from her… is death is overwhelming, but it is not very complicated.

What is simple are the words to acknowledge this. So the words that she needed to hear were: "I'm so sorry, this is so sad. I miss him too." So what is the power of a few simple words? And why do we feel like sometimes those words aren't enough?

Her name's Megan Devine, she's an incredible writer about grief. She said people come back at you with sort of simple things, but it's the wrong thing. They also would say to her after her partner died, "Oh, you'll find someone else," because she was a young woman at the time. "You're going to be okay, you'll get through this."

And what she longed to hear was, "It's okay, you're not okay." 

Just this validation of the experience of having your world shattered, and not attaching any sort of expectation that she would have to sort of be a certain way to show that the person who was trying to comfort her had done a good job. I think that that can be something when you're in deep grief, when people bring by dinners and people like, say, "Let me know if I can do anything."

All of a sudden the person in grief is the one who has to do the work to say, "Thank you so much for showing up for me. And actually, could you go to the store for me, because I haven't gone to the store."

Instead, what if we try to be the person who's just like, "I'm going to take your dogs for a walk every Thursday." Or "I'm going to call you every Sunday evening at 6pm. And you don't have to pick up but I'm just going to do that." 

Try to be that friend where they don't have to work hard.

You frequently mentioned this idea of a conversation partner. So frame that up for us?

I just think it's important to think about when you're having a hard conversation, it is in the context of a relationship. This isn't just saying talking points to one another, and we're going to see who's going to win in the end. That's not how conversation works. 

It's you who's figuring out your relationship. Can you listen to me? Can you allow me to be different from you? Can we come together around the things that we both value? That's what's happening when you're talking about hard things with someone. 

And sometimes you may come to the end of a really honest conversation and realize, "Oh, we are not going to agree on this. And, actually, I don't need to talk with you about this anymore. I can move on." 

I want to make sure I'm hearing what the person is telling me. I want to say what I need to say, and I'm going to tend to the relationship. 

Produced by Sarah-Joyce Battersby. Written By Lito Howse. Q&A edited for clarity and length.