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How to Have “The Talk” About End-of-Life Plans Without Everyone Running for the Hills

Writer's picture: Beth MontgomeryBeth Montgomery
traveling, compass, end-of-life planning

Let’s be honest: talking to your parents about their end-of-life plans isn’t the dinner table chat anyone’s dying to have (pun intended). But avoiding it? That’s how you end up stressed, scrambling, and second-guessing when you least need it.


Still, getting this conversation started can feel like herding cats.


So here's a friendly script and some practical steps to make it less awkward and more actionable.


Step 1: Break the Ice with Humor

You don’t need to kick off with, “So, about your inevitable death…” Instead, ease into it with a lighthearted approach. Try something like:“Hey, Mom, remember that time you told me I owed you $200? Let’s talk about what happens if I still haven’t paid it back… in 50 years.”


Humor diffuses tension and opens the door for a serious topic. Plus, your parent is less likely to give you the side-eye if they’re laughing.


Step 2: Shift the Focus

This isn’t just about them—it’s about you, too. Gently remind them that knowing their wishes will help you honor them and avoid unnecessary stress during tough times.“I want to make sure I’m doing what you would want, not guessing in a moment of crisis.”


This takes the spotlight off the uncomfortable topic of mortality and reframes it as a gift they can give you: clarity and peace of mind.


Step 3: Ask Specific Questions

Open-ended “What do you want?” questions can feel overwhelming. Instead, go for bite-sized topics:

  • “Have you thought about a living will or healthcare proxy?”

  • “Would you prefer burial, cremation, or donating your body to science?”

  • “What’s something you want remembered about you?”


Be prepared for jokes, side tangents, or even resistance. Just stay patient and curious.


Step 4: Share Your Plan

Lead by example! If you’ve already thought about your own wishes, share them. It shows you’re walking the walk.“I’ve been thinking about my own plans too. I’ve decided I want a Viking funeral… just kidding. Sort of. But seriously, I’ve got a death doula helping me figure it all out.”


Introducing a death doula might get some raised eyebrows, but it’s also an opportunity to explain how someone like me can help guide these conversations, provide support, and simplify the process for everyone involved.


Step 5: Keep It Collaborative

This isn’t a one-and-done discussion. It’s a series of conversations that evolve over time. Once the door is open, suggest tackling one thing at a time.“Let’s start small. Maybe we can talk about your healthcare wishes this week, and the financial stuff later.”


By breaking it down into manageable pieces, it becomes less daunting and more like a partnership.


Final Thoughts

Having these conversations now saves your family from confusion and heartache later. It’s not about making it perfect—it’s about starting somewhere.


Want support to make this process easier? Join me in February for my Planning Intensive, where we’ll dive into creating clear, compassionate end-of-life plans—for yourself and your loved ones.


Because when it comes to this stuff, the hardest part is getting started. Let’s do it together.

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