Estate Planning Conversations Around the Holiday Table

Nearly 55% of U.S. adults don’t have a will or estate plan in place. Probate, when no clear plan exists, can consume 3–7% of an estate’s value and drag on for months or even years. And 58% of families without an estate plan report disputes or conflicts after a loved one’s death. These numbers highlight why planning ahead matters—but the holidays offer a gentler, more natural moment to start the conversation.

The holiday season brings something rare: multiple generations gathered under one roof. Between shared meals, familiar stories, and traditions passed down over the years, there’s a warmth that encourages reflection. In these moments, it becomes easier—and often more meaningful—to talk about the future, including estate planning.

For many families, the topic feels uncomfortable. But estate planning isn’t about focusing on worst-case scenarios. It’s about giving your loved ones clarity, easing future burdens, and preserving the values and traditions that make your family unique.

What Estate Planning Really Means

Estate planning isn’t just for the wealthy. It’s about control, clarity, care, efficiency, and legacy—deciding who will make decisions if you cannot, protecting dependents, simplifying legal processes, and ensuring the stories and heirlooms that matter most are carried forward.

Questions Adult Children Can Ask Their Parents

Adult children often hesitate to bring up the topic, but asking thoughtful questions now can prevent confusion later. Consider easing into the conversation during a quiet moment, such as a walk or while cleaning up after a meal.

Do you have an up-to-date will or trust in place?

Who have you chosen to make financial and medical decisions if you’re unable to?

Have you shared your wishes for medical care and end-of-life planning?

If something happened tomorrow, would we know where to find your important documents and accounts?

Are there heirlooms or traditions you’d like us to know the stories behind?

Do you feel confident that the people you’ve chosen to handle your affairs are still the right ones?

Questions Parents Can Ask Their Adult Children

Parents can also open the door to meaningful dialogue. These conversations help younger generations think proactively about their future and their role in family planning.

Do you know where to find my important documents in case of an emergency?

Have you considered creating your own will or an estate plan?

If you received an inheritance tomorrow, would you know what to do with it — or who to turn to for help?

Are there family keepsakes or traditions you’d be heartbroken not to have carried forward?

If you had to step in to help us — financially or medically — what support would you need?

How to Bring Up the Topic Without Making It Formal

You don’t need to schedule a family meeting or turn the holiday dinner into a planning session. Instead, try bringing up one or two questions during a quiet moment—on a morning walk, while prepping dessert, or when sharing stories about past generations. Small, natural conversations often have the greatest impact.

A Gift of Clarity and Love

Talking about estate planning during the holidays isn’t about paperwork—it’s about protecting the people who matter most to you. These conversations help prevent legal challenges, reduce stress during crisis, and keep family relationships strong.

If you’re unsure where to start or want guidance in navigating these discussions, consider reaching out to a trusted advisor. A little clarity today can bring peace of mind for years to come.