It’s Time to Talk About ‘Hard Things’

Welcome to the world of Anna Sale — the host of “Death, Sex & Money” — where the topics that are the most painful to talk about are also the ripest for discussion.,


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“This sounds like a question not about how to have a hard conversation, but whether to have one.”

— Anna Sale, the author of “Let’s Talk About Hard Things”

The sex could be better, but you aren’t sure how to bring it up. A friend’s husband dies, but you’re at a loss for what to say. You have more money than your peers, but you feel the need to keep it secret. Welcome to Anna Sale’s world, where the topics that are hardest to talk about become the ripest for discussion.

Seven years ago, Ms. Sale started “Death, Sex & Money,” a podcast from WNYC Studios about “the things that mattered most in life but that we talked about least.” After interviewing everyone from a “sugar baby” about her double life to veterinarians about their profession’s high suicide rate, she has published a book, “Let’s Talk About Hard Things.”

In addition to death, sex and money, Ms. Sale adds family and identity to her short list of hard topics. “My goal,” Ms. Sale wrote, “is to open up that buried passageway between us, to let us connect and understand our lives more clearly.”

While the stakes are high for opening up, so are the rewards. “If you don’t have the hard conversation, you’re preventing both of you from knowing what could have happened if you tried,” Ms. Sale said.

Navigating these tough topics is more challenging than it’s ever been. Trust in institutions has eroded and religious affiliation has declined, leading to fewer shared rituals. “More and more, these hard things fall on us as individuals to navigate on our own,” she said. “Your friend dies who wasn’t part of a religious identity — what are you going to do for the funeral service? You have to talk about it and you make a plan for it.”

When beginning a tough conversation, she suggests signaling that you’re going into a different mode. “Say something like, ‘Hey, I’ve been thinking about something’ or ‘Is now a good time to talk about something important?'”

“They feel invited in rather than ambushed,” she explained.

Also, study body language to understand “where you can push more, and what needs to be left for another time.” And short simple phrases such as “What I want has changed,” “All I’m asking for is understanding” and “Tell me that story again,” can help bring words to the unspoken. Most importantly, it’s essential to open your ears. “A conversation can either shrivel or bloom depending on how one listens,” she wrote.

And remember, “No matter how much effort you put into these conversations, they will often end without resolving the unsettled feeling that prompted them,” she wrote.

Still, she believes conversations — the tough ones — are invaluable not for what they fix, but for what they engender. “I’m drawn to them,” she said, “because they offer incredible moments of connection that can help you in your moments of deepest isolation and alienation.”

In a previous newsletter, we invited In Her Words readers to tell us about the tough discussions they’ve been yearning to have. Ms. Sale responded with specific advice to four of them.

Amanda from Indiana

Amanda is a polyamorous and bisexual woman. She is in a long distance relationship with three women, and her conservative Christian family doesn’t know. Amanda writes:

“There’s talks about my girlfriends coming to visit me and I’m tired of hiding who I am … I’ve never felt so loved and in love as I do with my polyfam and it hurts me to have to put up with the judgment of me being ‘single’ at my age (mid 30s) when I’m not.”

She has concerns about the possible repercussions of telling her conservative family. “They’re the only family I have left, so to lose them is a little frightening.”

This sounds like a question not about how to have a hard conversation, but whether to have one. As we become adults, all of us have to figure out when to draw lines and choose direct honesty about who we are and how we differ from our families of origin. As you write, the stakes of having this hard conversation are high. You want your family to know who you are, but you also fear losing them if they cannot accept you.

If you choose to have this conversation, I want to assure you that even the most perfect choice of words will not control their reactions. They may have trouble accepting you, and they may say hurtful and painful things to you that could rupture your relationship, for at least the short term and maybe forever.

If you decide you need to be fully honest with your family, I suggest you open the conversation by expressing three things: 1. You want to share something with them that is really important to you. 2. You love them and really value having them in your life and you are afraid of losing them. 3. You have found love in a way that may be unfamiliar to them, but you are very happy. Then, maybe ask if they have any questions and if they want to meet your girlfriends when they visit.

I would also suggest you warn your girlfriends before you talk with your family so they are ready to talk over whatever reactions your family members have. You don’t need to absorb this alone.

Rosemary from Washington

Rosemary is 76 years old, and though she has no life-threatening medical conditions, she has been getting all of her affairs in order to make her passing, whenever it happens, smooth for her children. She has given important documents and instructions to her eldest son and trusts him to do what she wishes. She writes:

“The problem is that he doesn’t want to know or discuss any of this since he wants me to live forever. Same with my other kids. I’ve tried to discuss this with each of them, but they just don’t want to hear anything about my prospective death, even if that is going to be 20 years from now.”

None of us wants to imagine that a day will come when someone we love will be gone. It’s stressful and hard, and if death doesn’t seem imminent, it’s easy for us to delay those conversations. But it sounds like your kids’ reluctance to talk about your end of life plans has become stressful for you.

I would suggest trying to open a conversation by making it clear that you are feeling stressed and a little lonely about not being able to explain your plans to them. Say something like, “I’d like to talk to you about something that’s important to me. Since I shared my end of life documents with you, I’ve realized that I’d really like to talk to you about what I considered as I made these decisions because I think they say a lot about what I value.”

Veronica from Nebraska

Veronica noticed sexist and racist remarks posted online by her sister’s boyfriend. After calling him out, the relationship between her and her sister became strained and distant. Veronica feels concerned about her sister continuing the relationship and wants to talk about it with her. She writes:

My sister has a 6-year-old daughter who is biracial. I fear for my niece mostly and how her identity could be negatively impacted by his presence.

How do I come to my sister with my worries? I am afraid I will come off condescending or ill-intentioned. I want the best for her. I also have a deep desire to be heard.”

You are expressing three important things. You love your sister and want the best for her. You don’t want her to shut you out if she feels judged by you. You also need to feel like she’s acknowledging your concerns.

I would begin with that. This is one of those conversations where it’s as important to pay attention to how you’re expressing yourself as what you’re saying. Try to lean into curiosity more than judgment. I would try to think of some questions you have for your sister about her relationship. What is good about it? What does she love about him? What does she make of the online comments? Does she feel pulled between him and you?

This information will help you understand more about where your sister is coming from, and may help you be more clear about your concerns. But this hard conversation may just lead you to another hard choice: If they stay together, and you think he’s an unsuitable partner, you will have to decide how much of a relationship you can have with your sister and her boyfriend.

Lynn from Washington

When Lynn’s son sustained a traumatic brain injury, she and her husband flew out to see him. While there, their daughter-in-law expressed resentment toward them that she’d been harboring for years. Lynn writes:

She no longer wants any communication with us and has said there is no chance of a reconciliation. Not only do we have the worry about our son, but we are left out of knowing what is really going on with our son. We don’t know how to bridge this chasm of hatred towards us when she will not talk to us and we are unaware of what caused this anger.

Our son does call us once a week, but we don’t bring any of this up due to the brain injury. This has been very hurtful and we don’t see a way to go forward.”

Your daughter-in-law has, for now, not given you any openings to offer repair, or even understanding of why she is hurt and angry. She has drawn the line, for now, that she doesn’t want to have any conversation with you. In time, you may consider reaching out to your daughter-in-law with a letter or an email. I would focus on your love for your son, the pain you feel from your estrangement from her and your desire to support them both as he recovers. Write about the present and future, rather than litigating any events from the past. Describe the kind of relationship you wish to have with them and also tell her that you want to listen and understand more about what she needs. You cannot control her response, but you are offering an opening, which unfortunately is all you can do in situations like this.

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