Most of us know we should have it. Very few of us do. The conversation about what happens when we die — our wishes, our documents, our plans for the people we leave behind — sits at the top of the "important but not urgent" list until, suddenly, it's urgent.
This article is an invitation to have that conversation before the crisis arrives. Not because it's easy. Because it's love.
Why We Avoid It
The avoidance isn't irrational. We associate planning for death with inviting it — as if acknowledging mortality somehow accelerates it. We tell ourselves there's time. We don't want to upset our partner, our parents, our adult children.
And underneath all of it: it's simply uncomfortable to sit with the fact that we will die, and that the people we love will grieve us.
But here is what's also true: avoiding the conversation doesn't protect anyone. It only transfers the burden — from us, to them, in the hardest possible moment.
What the Conversation Actually Is
It doesn't have to be a formal sit-down with a lawyer present. It can begin simply:
- "I've been thinking about getting our documents organized."
- "Do you know where everything is, if something happened to me?"
- "I want to make sure you're not left figuring things out alone."
That's it. One sentence. From there, the conversation finds its own way — at the pace that feels right for your family.
What You Actually Need to Talk About
The most important areas to address with your loved ones:
- Where your important documents are (or how to access your Life Binder)
- Your healthcare wishes — including a healthcare directive or living will
- Who has legal authority to make decisions on your behalf (power of attorney)
- Your wishes for burial or cremation, and any preferences for a service
- Who gets what — and who knows where to find the will
- Any specific wishes that might not be obvious
When No One Wants to Bring It Up
Sometimes you're not the one who needs to start this conversation — you're the one who wants to have it with an aging parent, or a spouse who changes the subject. A few things that help:
- Lead with love, not logistics: "I want to make sure I can take care of things the way you'd want."
- Use a shared event as a bridge: a diagnosis in the family, a friend's loss, an article you read
- Frame it as mutual: "Let's do this together — for both of us."
- Start with the practical and move toward the personal
You might not get the conversation you hoped for on the first try. That's okay. Keep returning to it, gently.
The Gift on the Other Side
Families who have these conversations — imperfect as they are — consistently report the same thing afterward: relief. A sense of closeness. The feeling that they did something hard and important together.
That is what planning ahead actually feels like. Not morbid. Not dark. Just honest, and deeply loving.
Starting the Conversation — Your Checklist
- ☐ Identify the one person you most need to have this conversation with
- ☐ Choose a calm, unhurried moment — not a holiday or family gathering
- ☐ Lead with love: 'I want to make sure you're taken care of'
- ☐ Share where your important documents are (or create a Life Binder)
- ☐ Discuss your healthcare wishes and end-of-life preferences
- ☐ Ask them to share the same with you
- ☐ Follow up — one conversation is rarely enough
- ☐ Consider completing your Life Binder together
Alice Truman's workbook Not My Favorite Subject Either was written specifically for people who know they should prepare — but don't know where to start. It makes the conversation easier, and the planning manageable.
Not My Favorite Subject Either, But… — by Alice Truman — View on Amazon ↗