Cameron Huddleston regrets that she never got to talk to her dad about what he wanted after he died. He’d always shrug off the question and say, “Just sharpen my toes and hammer me into the ground,” says Huddleston, who went on to write Mom and Dad, We Need to Talk: How to Have Essential Conversations with Your Parents About Their Finances. Her father died from a heart attack at 61, without a will or any final wishes spelled out. “Looking back now, if I had taken the time to sit down with my dad and have a conversation, I think hearing that from his child might have had an impact,” she says. “That was one of the reasons I wrote the book. My dad is not the only one out there who didn’t plan.”
According to a 2018 national survey from The Conversation Project, a public engagement initiative dedicated to helping people express their wishes for end-of-life care, 92% of Americans say it’s important to talk about this stuff. A full 95% of Americans say they would be willing to talk about their wishes; 53% say they’d be relieved to have the discussion. And yet only 32% actually have. Patty Webster, an advisor on the project team, says that when it comes to this topic, “The biggest thing we hear is fear. People don’t want to worry their loved ones. They don’t want to upset anyone. But our fears are not accurate. People really do want to talk about this.” Shoshana Berger, co-author of A Beginner’s Guide to the End: Practical Advice for Living Life and Facing Death, agrees. “What’s really so encouraging and stunning and kind of sad is that people so want to talk about it, but they don’t know how.”
When it comes to approaching these crucial, complicated conversations with the people you care about the most, Berger’s coauthor BJ Miller, a hospice and palliative medicine physician at the UCSF Helen Diller Family Comprehensive Cancer Center, notes there is one vital thing to remember: “When you’re talking about death, you end up talking about love. That’s not just a trick, there’s truth in it.”
Breathe—Your Fears Are Totally Normal
The reason we avoid these conversations is simple: They’re hard, in so many ways. “First, there’s a stigma,” says Amy Pickard, who, after the unexpected death of her mother, created Good To Go!, an unconventional advance planning company that helps guide people through their end-of-life paperwork. People’s fear, she says, can come from a concern about being misunderstood. Some might worry that broaching the topic, she says, “means you’re greedy and want that person to die, and you want to know when you’re getting the money.” Others can be scared they might get emotional, or their loved ones will get emotional. “But why are we afraid of showing emotion to the people who love us most?” Pickard asks.
There’s superstition, too, when it comes to talking about death—if you talk about it, it’ll make it happen. (True story: It’s going to happen to all of us, no matter what!) But avoiding the subject can compound our fears and anxieties. “Uncertainty can be very anxiety-provoking for people. “What’s more uncertain than death?” asks Amanda Spray, PhD., a clinical associate professor in the Department of Psychiatry at NYU Langone Health. “But bringing some certainty to the ultimate of uncertain situations can be helpful.”
When people don’t have these talks, Webster notes, depression and anxiety increase for the living after the death of a loved one. For people who’ve had these conversations, depression goes down.
Find the Right Opener
Everyone’s “access point” is different. For instance, when Berger tried to discuss end-of-life plans with her mother, “She’d run away screaming. Until I asked her to tell me about her early life, the house she grew up in, then she was off to the races.” If you listen to what mattered to someone throughout their life, you can move on to the end—try, “I love knowing this about your life, maybe you can tell me about how you’d like the rest of your life to go?” These conversations “have this happy side effect of helping a loved one appreciate their life,” says Dr. Miller.
You can also start by sharing your own story. Dr. Spray recommends telling a parent or loved one that you are in the process of writing a will or designating a proxy, which can normalize the conversation. You might say: “I’m doing it, why don’t you do it with me? If you have nothing in place, what would you want?” Huddleston suggests sharing “a story about a friend whose parent died without a will or one who died with everything in place and how easy it was.” The news can also be a useful source for conversation-provoking stories (both Prince and Aretha Franklin died without wills, leading to an array of ongoing estate issues). Or ask your mom or dad how they dealt with the deaths of their own parents, says Pickard.
To help take some of the pressure off, Huddleston suggests acknowledging this is an inherently uncomfortable situation. Tell your loved ones, “This is difficult for me. I don’t want to think of a time when you’re no longer going to be in my life. But, if I know your wishes: What sort of funeral do you want? Do you want to be buried? Who should get your house?... When the time comes, and I am grieving, it’s one less thing for us to worry about.”
“As awkward as these conversations might seem, the consequences of not having them is so much worse,” she says.
Make It About Their Wishes
Press for details on what your loved ones want, and find out how you and they can make that happen. Huddleston recommends questions like, “Have you bought a cemetery plot? Is there a life insurance policy to pay for this? Do you have savings to help cover this cost?”
The Conversation Project and Good To Go both offer extensive lists of questions, prompts, and things to consider: The Conversation Project’s Starter Kit is available to download for free and Pickard offers her Departure File for sale for $100. These lists of questions can help remind you about details you might be considering, such as designation of a death care agent, child and pet care wishes, a list of accounts and who should manage them, and more: If you own cremains, where do you want the cremains to go after your death? Do you want music to be played at your cremation? Do you have a playlist?
Focus on your loved one’s quality of life and how this discussion helps lend control in a time that’s pretty uncontrollable. “That’s a way to motivate someone,” Webster says. Dr. Spray agrees: “Inevitably, this is going to happen to all of us. Being able to have some say can be really helpful.”
You might also “invoke what a kindness it is to do for the family, that will get people’s attention in a different way,” Dr. Miller says. He adds that, in the absence of these conversations, family members are likely to default to the most expensive options. Dr. Spray notes that when a crisis occurs, having a plan is its own comfort because it soothes those who remain. If there’s a lot of avoidance of the subject or bringing it up leads to arguments, she suggests family therapy or sitting down with an attorney to ease the process.
Consider the Time and Place(s)
One of the mottos of The Conversation Project is “Do this at the kitchen table, not in the ICU,” but choosing the best place and time depends on you and the person you want to talk with. People think the holidays are a good time for these conversations, but that can backfire, says Huddleston. “Don’t do it during the family meal; there might be people who don’t need to be there, and people are much more emotional.” One woman handed out Starter Kits at dessert over the holidays, Webster says, using the cheeky slogan, “No pie until you tell me how you want to live and die.” That went well for her. Another woman put kits on the table as place settings. She got crickets.
Don’t force the conversation or go in thinking you need to have it all out right then and there. If it’s not a good time, you can ask to schedule something in the future and come back to it when everyone’s ready.
Or print this article out, stick it on the fridge, and wait for someone to comment.
It Can Even Be Fun
Pickard suggests thinking, “How can I get this information across without dressing up like the grim reaper and make it more palatable and enjoyable?” A Good To Go! party involves inviting your “soul cluster” of close friends and family, bringing a dish based on a favorite recipe from a loved one, and serving booze and cocktails. (“If you’re going to talk about the hard stuff, you need the hard stuff,” she jokes). She’s even got a death-themed rock and roll soundtrack to set the mood. Then pass out the Departure File, and everyone can get to work documenting their wishes and sharing as they feel comfortable.
After Pickard’s mother and grandmother died, “I knew it was my job to get what I needed from my dad,” she says. “He came to a Good To Go! party, and I learned stuff about him that I never knew. When he came down with the flu at age 72, had to go to ICU, got sepsis, and died six days later, she was able to go into that emergency situation “rock solid, knowing every single thing he wanted.”
It’s Never One and Done
“Prepare yourself for a series of loving conversations,” says Webster. “We joke that we should have been The Conversations Project.” Before her 18-year-old son went to college, she tried to get him to choose his health care proxy. Asking him over dinner didn’t work. The perfect time turned out to be their 6-hour-drive to his new college together.
For her book, Huddleston interviewed a woman who wanted to talk to her parents about wills. They jokingly dodged the question and asked, "Are you just trying to get rid of us?” But a month later, they’d taken action. If they’re initially hesitant, don’t give up; talking “becomes a muscle that you flex and condition regularly,” says Berger.
Pickard adds, “When someone in your family is brave enough to bring this up, don’t change the subject. Allow them to talk about it, give them the permission, it’s going to ease their mind. It’s ultimately going to be in your best interest.”
Don’t Wait for an Emergency
Huddleston is a proponent of starting to have these conversations with your kids when they’re young. It becomes something that the family talks about, and it’s easier to keep the dialogue going, she says. You can tell them, “Don’t worry, we’re okay. Your father and I want to have this conversation because we want you to know that we have a plan, and when the time comes, you don’t have to worry about anything.” Her kids range in age from 8 to 15, and “they know who their guardian is, we’ve told them we want to be cremated. My husband says he wants his ashes buried with a tree. Our kids know our wishes.”
After her mom’s sudden death, Pickard faced a million questions about what she would have wanted. “While you’re grieving, the last thing you want to do is become a party planner, a detective, and a travel agent,” she says. She created the Departure File to prevent others from having to go through what she’d had to deal with. “It’s so important to do while you’re young and healthy. We’re taught to prepare for natural disasters that may or may not happen, but we’re not taught to talk about the thing that happens to every human being. It should just be part of your preparedness. It allows the dying and the loved ones to spend their energy and focus on what’s important, which is love.”