Podcast host Anna Sale wants you to learn how to have hard conversations

Regardless of who you are or where you live, the past year has probably forced you to have uncomfortable but necessary conversations. Between the pandemic and its incalculable toll, the tense 2020 presidential election and the deaths of Breonna Taylor, George Floyd and many others at the hands of police, most of us have struggled to put our feelings into words – and talk frankly with others.

Enter Anna Sale’s new book, Let’s Talk About Hard Things. Sale, who is the host of the podcast Death, Sex and Money, has become an expert on difficult conversations – the kind that initially make you squirm, but almost always leave you wanting more. After seven years of hosting the show, Sale knows how to cut through the discomfort with her guests. She broaches every topic – from infidelity to infertility – in a way that centers warmth, trust and vulnerability.

I reached her over Zoom at her cabin in Cody, Wyoming, to talk about why some topics are still so thorny and to find out her best advice for talking about hard things.

This past year has forced all of us to be with ourselves. And within that time frame, we’ve also been forced to have a lot of difficult, uncomfortable conversations about race, politics and money. Do you think that’s changed how we approach difficult things?

Well, I’m hoping it has. I think we’re in this moment where we’re all forced to confront really hard conversations. We’re all out of our depth. We’re all feeling loss, questioning and a lack of certainty. And that is worth talking about on its own. Hard conversations are generative when you let someone in to what is uncertain or troubling for you.

The phenomenon of the pandemic, in imposing itself on all of our lives and showing us how fragile so many of our institutions and structures are, has hopefully led to some of us thinking, “Oh we could do this differently”. It leads us to an opening where we can say: “How do we want all this to work differently?”

Some of the hardest conversations to have are around death. You talk about some of the rituals that usually accompany mourning in the book – rituals that were unavailable to us this year. People have had to grieve in a really different way, including in a digital space. Are those virtual conversations as impactful?

I think you can have meaningful conversations in digital spaces – this is what we’re doing right now. To me it’s just about trying to figure out ways to infuse more one-on-one human connection in the ways that we interact digitally.

I think what’s important when you feel you don’t know what to say to make it better is to acknowledge that your job in that moment is not to make it better. Instead, it’s to show up and offer care. And listen, and say, I’m so sorry. And let go of the expectation that you’re going to say something that’s going to make a grieving person feel better.

I think digital communication can be incredibly meaningful. I love that that dimension exists. But because the pandemic has required us to do it in words rather than say, hugs or time together, take that extra step to show up in a more human way.

You have two small kids. Parenting through Covid has been an inescapable conversation. One thing that fascinates me is how surprised we all were that it’s been this hard for this many people. But since we’ve all been finding parenting, even pre-pandemic, incredibly difficult to manage, why haven’t we been having those uncomfortable conversations with each other as parents before?

When you are encountering something that feels impossible, often our first emotional response is to ask: “What have I [personally] done wrong that this isn’t working?”

I think that pre-pandemic, a lot of parents were asking how on earth they were supposed to pay for childcare, get work done, move up in their career. But what the complete collapse of the public education and childcare infrastructure in America revealed is that this isn’t a struggle that my individual family has been having a hard time with. Now I’m seeing how systemic this is, these strains and these tensions. And I’m finally noticing it’s not me, it’s the system.

In that way, it’s positive. Because it’s revealed something that used to cause so much personal shame and is now creating conversation about some big choices we have to make together about how we want our society to work.

That idea of personal shame, do you think that’s also why we still find money so hard to talk about?

There’s so many ways to feel shame about money. You feel shame if you feel like you don’t have enough. You feel shame if you feel like you have more than you personally earned. In America, I think you also feel shame if you’re not part of the big middle.

When you look at numbers, it’s very clear that the middle class is shrinking in the US. But in terms of self-identification, the idea of being middle class has not shrunk. There’s this feeling that you want to be part of it – there’s this ethos in America that that’s the honorable place to be. And so if you don’t want to reveal that you have less than you think you ought to, or you have more than you think you’ve earned, there’s gonna be a lot of secrecy, right?

Part of what’s getting in the way here are these really blunt myths we have about money. It gets to this “systems versus personal agency” question that I was talking about with parenting. What we have or do not have is a consequence of a lot of luck (or misfortune) that we had nothing to do with, as far as our family’s histories or generational wealth.

I graduated college in 2003. And I will tell you, I know that my earnings are what they are because I did not graduate in 2009. I got a job with benefits right out of school, because people were hiring and that compounds.

Everything we have or don’t have is this combination of things we can’t control and the things we can. When you start by acknowledging that, you cut through some of that shame.

What do you say to people who avoid hard conversations because they just aren’t sure what to say in the face of something uncomfortable?

Letting go of the idea that you need to fix something is really important.

When someone reveals something that they’re struggling with, or something painful that happened to them, I often find myself saying, “I’m so sorry, thank you for sharing that with me.” Let’s acknowledge that you’ve just said something, that there’s nothing I can say that’s gonna lift that pain. By saying that, you’re focusing on the conversation on what they’ve disclosed to you. You can also talk about how you’re talking about it. You can say, “I don’t know what to say right now. But I just want to tell you, I’m really sorry to know that.” Or “I’m really sorry, that happened to you, but I’m here for you. And I want to understand if there’s ways I can be helpful.”

If you are a person who is disclosing something painful and what you hear back is, “you should try yoga or deep breathing, that really helps me,” that’s not going to help. So when you don’t know what to say, that’s OK. That shows that you’re listening, you know?

• This article was amended on 26 May 2021. The sub-heading previously referred to Anna Sale’s podcast as Sex, Death & Money. It is Death, Sex & Money.