How to Start a Conversation About Estate Planning Over the Holidays
The holidays are for family, food, and a little reflection—so why not use this rare together time to start a conversation about the future? Talking about estate planning might not feel festive, but it’s one of the most thoughtful things you can do for the people you love. The key is to approach it gently and in the spirit of caring.
Here’s how to make it less awkward and more productive.
1. Pick Your Moment Wisely
Don’t drop the estate planning bomb mid-gingerbread cookie decorating or during a heated game of charades. Instead, find a calm moment—maybe over coffee or a quiet walk. A low-pressure setting makes it easier to have a meaningful conversation.
2. Use Stories to Start the Conversation
Rather than launching into “We need to talk about wills,” try sharing a story. Maybe it’s about someone you know who didn’t plan ahead and the complications their family faced—or someone who did and how much smoother things went. Stories make it personal and relatable without feeling like a lecture.
Example: “I was reading about how much easier things are for families when there’s a will in place. It made me realize we’ve never talked about what we’d want to happen.”
3. Focus on the Upside
Nobody likes to think about worst-case scenarios. Instead of talking about what could go wrong, frame estate planning as something empowering. It’s about making sure your wishes are honored and reducing stress for your family.
Example: “Planning ahead means everyone can focus on being together, instead of worrying about decisions during a tough time.”
4. Come Prepared with Easy Options
Turning a conversation into action is much easier when you have the right tools at hand. Share user-friendly resources, like the educational guides and articles available on Epilogue's Learn Center or blog, or point them directly to the online Will platform on the site to help them get started effortlessly.
Example: “I found this online tool that makes writing a will really straightforward. I can show it to you if you’re curious.”
5. Plant the Seed, Then Let It Grow
Not everyone will be ready to dive into estate planning on the spot, and that’s fine. Just starting the conversation is a win. Let them know you’re available to chat more when the time feels right.
The Bottom Line
Talking about estate planning isn’t just about logistics—it’s an act of love. It’s one of the best ways to protect your family and make sure your wishes are respected. And what better time to start the conversation than when everyone’s gathered together?
After all, the holidays are about care and connection—and planning for the future is one of the most thoughtful gifts you can give.
