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Let's Talk About the Hard Things With Anna Sale

In her new book, the popular podcast host of 'Death, Sex & Money' offers guidance on approaching tough conversations

By Randi Mazzella

Anna Sale thought she knew a lot about asking difficult questions. For many years, Sale was a political reporter. It was her job to do the research and find the right answers.

But like many people, Sale, 40, was less forthcoming in her personal life. She believes this reluctance to open up was part of the reason she was blindsided when her marriage ended. Sale says, "I didn't see it coming, and I fell apart. For the first time in my life, I felt out of control."

Illustration of a couple sitting down to a tough conversation. Hard conversations, Anna Sale, Next Avenue
Credit: Getty

What helped Sale to start healing from her divorce was the realization that she was not alone in her grief. Sale explains, "I started having real conversations with my friends and family where they shared their own losses and disappointments. I heard how they made their way forward through messy moments. Listening to their stories gave me companionship during a difficult time of transition in my life." (Sale has since remarried.)

"I started having real conversations with my friends and family where they shared their own losses and disappointments."

Sale's experience led her to launch "Death, Sex & Money," the popular interview-style podcast which debuted on New York City public radio station WNYC in 2014. As host, Sale talks with guests about the messy moments in their lives, delving into important topics that many people are uncomfortable discussing.

On May 4, Sale's first book, "Let's Talk About Hard Things" (based on the podcast), will be released. Sale graciously allowed Next Avenue to turn the tables and ask her a few big questions:

Next Avenue: The podcast title includes Death, Sex and Money, but you add in Family and Identity in the book. Why?

Anna Sale:  In long-term relationships like with family, we are assigned roles, a shared history. On the one hand, these strong bonds can mean there is a higher degree of trust. But it can also be hard to break free of bad communication patterns that have developed over the years. We have common origins, but as we age, we separate, and we may be unlike members of our family. And that can be really hard to talk about.

As for identity, I felt I would be remiss not to include this topic in 2021. Conversations about identity and race can be paralyzing. We may worry that we will say the wrong thing, and some of us probably will. The key is to approach the subject with humility and a genuine desire to listen and learn about others' perspectives.


Do you think the pandemic has caused people to have trouble connecting?

Yes, but I actually think this disconnect started before the pandemic. Years ago, people spent more time together. They gathered at the community church; they did their financial transactions in person at the local bank. These rituals reinforced bonds between people. 

Now we do everything online. We have less connection, less trust with the people in our community. The pandemic isolated people even further, since they haven't even been able to socialize with close friends and family for a year.  

But don't people share a lot with one another – maybe even overshare on social media?

We have moved away from sharing our lives with friends and family in an intimate, honest way. There is a big difference between the performative declarations people make on Facebook or Instagram and really sharing. Posts on social media are not [nurturing an intimate] relationship in the same way the kinds of conversations I'm urging us to have more of.

Why don't people have more intimate conversations?

When someone asks, 'How are you doing?' there is a natural inclination to say 'Fine.' Especially this past year, if your losses have been small, you may not want to admit that you are having a tough time or feeling isolated. But acknowledging that you aren't doing well or that some things have been hard opens up a space for an intimate conversation.

There is a quote in the book from Ann Simpson, an older friend of mine: 'Openness leads to openness.' If you are willing to be honest, and open, others will follow that lead.

"All of us want to feel heard. We are fighting to be heard so much that sometimes we don't listen."

What are some hard conversations that people tend to regret not having?

Conversations around death and grief are tough. When someone is sick, the focus tends to be on treatment options and logistics concerning their care. Sometimes we don't ask about the person's feelings and if they are scared about what will happen next. People wish they had acknowledged the sickness and talked about death with their loved ones.

Money is another topic we avoid because it is uncomfortable to discuss. Parents want their kids to understand family finances, and yet many don't talk about money with their kids. And when friends don't talk about money, it can be very isolating, especially if one is experiencing financial issues.

Conversations about sex seem to happen a lot when we are younger but then…

We stop talking about sex because we fear our feelings aren't normal or that we are the only ones experiencing changes in our bodies as we age. But we need to talk about sex in midlife. When you discuss your worries honestly, you may discover that others have the same feelings or concerns and you start to feel less alone.

How do you get started talking about hard things?

Make sure it is a good time for both parties to speak. Let the other person know that you want to have a more delicate conversation, more than idle chit-chat. Create a good space and lower the potential for volatility.

You can open with, 'Can I tell you something? or say, 'I've been thinking…' Don't start with criticism. You want to relay your experience, but signal that you are open to hearing the other person, too.

What is one of the biggest mistakes people make when they set out to have a hard conversation?

You have to be willing to listen to the other person. All of us want to feel heard. We are fighting to be heard so much that sometimes we don't listen. To have a connecting talk, you have to want to understand how the other person feels.

Also, it lightens the pressure to acknowledge that you might not have a resolution at the end of the conversation. The goal should be to understand each other better, even if that doesn't lead to reconciliation or agreement.

How do you tell someone something they don't want to hear?

Whether it's breaking up with a romantic partner or ending a friendship, sometimes a relationship doesn't work out or you need to take some time away.

When you're saying something that you think might hurt someone's feelings or be an outcome they don't want, try to say it in a respectful way. But you're not responsible for making sure they agree with you or don't feel hurt. It's okay to do something for yourself.

Randi Mazzella
Randi Mazzella is a freelance writer specializing in a wide range of topics from parenting to pop culture to life after 50. She is a mother of three and lives in New Jersey with her husband and teenage son.  Read more of her work on Read More
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