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It was late Monday afternoon. I sat next to Dad on the padded bench in our childhood living room. I had taken unexpected time off from helping women get their financial lives in shape to fly across the country for what I knew would be an important and incredibly difficult conversation.
It happened to be “quiet hour,” a tradition my parents had honored for decades — a time for a bourbon and water while my four sisters and I giggled in the bathtub or sat quietly at their feet.
But those days felt long behind us.
Dad was now 78, and I was there to say goodbye. By Friday, he would be gone.
As I leaned against his shoulder and held his hand, I could tell he was still trying to be there for me — even as it was clear he was ready to move on. In his humble and caring way, he listened as I stumbled through words that felt awkward and inadequate.
How do you do this?
How do you talk to your kids about your death?
As the author of Positive Money — 7 Principles for Living a Rich Life, a mother of five, partner in a strong marriage and a new grandmother, I’ve pondered this question often. Death is a mark in our legacy. How it's handled, planned for and processed can have significant implications emotionally and practically. It’s why the second principle of my book states that when you’re aware of the beliefs and behaviors you inherit and pass along, you’re more intentional about your actions today.
Thankfully, death and dying aren’t taboo topics in our household. Our kids — ranging in age from 24 to 38 — have experienced the passing of grandparents, beloved pets and others close to them. They’ve faced hard things and know they can come to us for support as we’ve encouraged discussions around big questions like, “What happens when we die?” or “Do you believe in the right to die?”
In recent years, we’ve had more opportunities to talk about death with the passing of two family members. When Mom died in 2019 after 10 years of suffering with dementia, her death was a relief and a sorrow. During that time, I would share what felt appropriate, reflecting on the loss of someone who’s still physically present while also finding new love for them in unexpected ways. The older children could relate better than the younger, but that made sense.
In early 2021, we lost my 28-year-old nephew in a car accident. He was one of 12 cousins, all around his age, so the impact of his loss made me appreciate the deep relationships our extended family had formed. I became aware of how I can learn from them beyond what they’re learning from us.
In the months that followed, celebrations of his life reflected the many gifts he left and the different ways we grieve. Even today, he is remembered at family gatherings, as his spirit is cherished and lasting.
These experiences have helped our family and my clients be better prepared for the inevitable, knowing that context, history, culture and capacity play a role. Three things I have learned along the way, in research and experiences, are what I call the three “Es.”
Step 1 — Set and Manage Expectations
Conversations about death are uncomfortable for many of us. In a recent study of wills and estate planning behavior, more than 50 percent of respondents didn’t have a will at all. This is why being clear about expectations can be a critical and essential step to having a productive conversation.
· What is your goal or intention?
· What matters most to you or others?
· What should you consider before you engage in the process?
For example, we put off updating our estate documents after my first marriage ended in divorce, and we blended as a family. I was sleepless and worried about the impact of something happening to us. How would our loved ones know what to do or have the resources and protections they deserved? Where would they find what they needed? Have we done enough? The worry was so present that we made sure to complete those updates, with an urgent ASAP deadline.
Step 2 — Plan the Engagement(s)
Once expectations are clear, the next step is engagement with the family. If your goal or intention is to prepare your estate for your next of kin, sharing details like what you want for your funeral service may be difficult for your loved ones. This makes initiating those tough conversations all the more important.
For example, when we asked our oldest child to serve as executor, she agreed. However, we didn’t give her much time to think about it, so she may have said yes without fully understanding what she signed up for. Now, seven years later, with more conversations and knowledge under our belts, we’ve reopened the discussion of who would be best suited.
Other best practices include scheduling family meetings to share thoughts and wishes before committing them to paper. If such meetings aren’t expected or potentially difficult to manage, consider hiring a professional to help navigate the practical or emotional dimensions.
Step 3 — Make Room for Emotions
When talking to your kids about your death, expect and even welcome emotions. Model being curious and accepting of them. Listen for concerns behind the emotion, and validate rather than dismiss them. After all, the ultimate conversation — if we’re so lucky to have it like I did with my father — will be emotional. And when the tears come, I like to think of them as just another way of showing love, saying goodbye and clearing the way for the next chapter of life — when death do we part.
How many of YOU have a will? Have you talked to your kids about death? Let us know in the comments below.
