Let’s be honest: most families would rather discuss literally anything else. Politics at Thanksgiving? Fine. Your cousin’s crypto investments? Sure. But death? Suddenly everyone needs to check on a casserole that doesn’t exist.
Here’s the thing, though, having this conversation is one of the most loving things you can do for the people you care about. It’s not morbid. It’s not giving up. It’s giving a gift. So let’s talk about how to actually do it.
Pick the Right Moment (Hint: It’s Not at Grandma’s Birthday)
Timing matters. You want a calm, private setting where people aren’t already emotionally maxed out. A quiet afternoon at home works. So does a walk, a long car ride, or sitting on the porch after dinner.
What doesn’t work: funerals, hospital waiting rooms, or the middle of your nephew’s graduation party. Read the room.
Start with Why, Not What
Don’t open with “So, about my burial preferences…” That’s a lot.
Instead, try something like:
- “I’ve been thinking about how I want to make things easier for you all someday.”
- “I read something that made me realize we’ve never really talked about this stuff.”
- “I love you, and part of loving you is not leaving you guessing about what I’d want.”
Leading with your intention—care, love, wanting to spare them stress—softens the whole thing.
Give Permission to Be Uncomfortable
Acknowledge the elephant. Say it out loud: “I know this is weird. It’s weird for me too. But I’d rather be awkward together for twenty minutes than leave you all arguing over whether I wanted roses or lilies.”
When you name the discomfort, it loses some of its power. And often, people are relieved someone finally said it.
Be Specific, But Not Overwhelming
You don’t need to cover everything in one conversation. Start with the basics:
- Do you have a will? Where is it?
- Do you have preferences about medical intervention?
- Burial or cremation? Any strong feelings about a service?
- Is there someone you’d want making decisions if you couldn’t?
You can always have follow-up conversations. This isn’t a one-and-done contract negotiation.
Let Them React However They React
Some people will want to dive deep. Others will crack jokes. Your sister might cry. Your dad might change the subject to the weather three times. That’s okay.
You’re planting a seed. Not everyone processes at the same speed, and that’s not a failure. Just leave the door open: “We don’t have to figure it all out today. I just wanted you to know I’m willing to talk about it.”
Write It Down Anyway
Even if the conversation goes beautifully, write down your wishes. Put them somewhere findable. Tell at least one person where that somewhere is. If staring at a blank piece of paper feels overwhelming, a site like WhenIGo.io can walk you through all the questions and offer helpful information as you think through your wishes.
Because here’s the truth: grief makes people forget things. Stress makes people forget things. Heck, I forget where I put my keys while I’m holding them. A written document is a kindness to Future Them.
Remember What This Is Really About
This isn’t about death. It’s about love. It’s about saying: I care enough about you to have a hard conversation. I trust you with my wishes. I don’t want you to carry the weight of guessing.
That’s not awkward. That’s brave. That’s generous.
And if all else fails, you can always end with: “Anyway, I want ‘Dancing Queen’ played at my funeral, and if anyone objects, I’ll haunt them.”
The best conversations are the ones we almost didn’t have. Start small. Start imperfect. Just start.
