Holiday Moments That Make Estate Planning Easier

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 create delays that last months or even years. And when families don’t prepare, 58% report disputes or conflict after a loved one passes. These numbers highlight an important truth: planning ahead truly matters.

The holidays offer something rare—multiple generations gathered around one table, sharing meals, stories, and traditions. These warm, familiar moments often bring a sense of connection that the rest of the year can’t quite replicate. And while estate planning isn’t exactly festive conversation, these gatherings can create a natural opportunity to talk calmly and openly about the future.

A Gentle Way to Begin the Conversation

Estate planning discussions don’t need to be formal or heavy. A quiet walk after dinner, a cozy moment by the fire, or a simple conversation while cleaning up the kitchen can be the perfect setting to check in on each other’s plans and wishes.

Questions Adult Children Can Ask Their Parents

As families grow and responsibilities shift, adult children often want clarity so they can help confidently if the need ever arises. These questions can open a thoughtful, supportive dialogue:

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 may also want reassurance that younger generations are thinking ahead—and that everyone understands how to carry the family legacy forward. These questions can help open the door:

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?

Why These Conversations Matter

Estate planning isn’t only about assets—it’s about clarity, comfort, and care. It allows families to avoid unnecessary stress by ensuring everyone knows where documents are located, what medical decisions should look like, and how important property or heirlooms should be handled.

It also helps younger generations think about their own responsibilities, from guardianship decisions to creating a simple will or trust. Most importantly, these conversations reinforce values, traditions, and the intention behind each decision.

The True Gift: Peace of Mind

Framing estate planning as an act of love can make the topic easier. By sharing wishes now—briefly and calmly—families prevent confusion, disagreements, and emotional hardship later. The holidays are a natural time to begin this dialogue, gently and respectfully.

If you’re unsure where to start or would like guidance on navigating these conversations, consider reaching out to a trusted advisor. A small step now can bring lasting peace of mind for the people you love most.