How to Talk About End-of-Life While Living Well

Look, this is nobody’s favorite subject. You do not have to be at peace with the topic. But like many difficult things, it’s necessary and worth it.

Most people avoid this conversation not just because they are afraid of dying, but because they do not know how to start. It’s awkward. They worry about being morbid. They worry about upsetting someone they love. So they wait.

But I want to challenge you to push through that awkwardness. The conversations that happen before anyone is in crisis are the ones where you actually have time to be honest. There is no good substitute for them.

Why it matters

People who have had these conversations report something unexpected: it brought them closer. Not because talking about death is comfortable, but because it is honest. It requires naming what you value and what you want for the people left behind.

This is not new

Humans have been thinking about the topic of death for thousands of years. If you look to ancient religions, cultures, or philosophies, you’ll see this has been a major topic amongst humans for a long, long time. Stoic philosophy built memento mori, the practice of remembering you will die, into daily life. The resistance to this conversation is not universal. It is cultural and relatively recent.

I want to challenge that status quo. Some of the most meaningful relationships in my life have deepened as we have had to tackle the big scary things.

Where to begin

Start with now. How do you live? How do you want to live for the rest of your life? Start with what you already know. From there, you can start asking bigger questions. What do you want to happen when you die? Who do you want present? What do you want to leave behind? You do not need answers yet. Noticing the questions is enough to start.

Ask people you know who have lost loved ones what it taught them. Ask people you are close to and have a lot of respect for how they are thinking about life. Start folding this into your life from a place of curiosity.

What can it look like?

Start thinking about what you want your relationship with death to be. Do you want to resist at all costs? Spoiler: that probably won’t protect you indefinitely. Can you start to imagine a life where you live with the memory of people you were lucky enough to know and love who are no longer with us? The grief of missing them can live in that space.

My neighbors occasionally invite my husband and me to their dinner parties with their friends. These friends have been friends for a long time and always entertain us with stories of being young adults in the 1970s and their adventures since. It was clear this friend group had been through a lot. Deaths of first partners, raising kids, ups and downs of life, endless laughs. Regardless, they hung together, making the most of their time with one another.

By the next dinner party we were invited to, one of them had died. Bibette had been diagnosed with cancer and passed away the previous fall. This vibrant staple of these stories was gone. It was so, so sad. We left space for the deep sadness. Her partner, Rob, was cracked open with grief. And they found ways to honor her. We toasted to her and put a candle in a piece of pie for her birthday. Emotions were raw. People cried and celebrated. And it was beautiful.

Regardless of how comfortable you are thinking and talking about death, I want to challenge you to lean into it a little more. What could your relationship with loss look like if it were up to you? How do you want your loved ones to remember you?

And if you want a structured place to start to document what matters to you, Restfully's Legacy Organizer is built for this. No deadlines, no right order. Work through it at your own pace.