Around the Holiday Table: Estate Planning Reflections

The holidays are magical, aren't they? It's one of the few times in the year when families, spread across generations, gather under one roof. The sounds of laughter, the clinking of glasses, and the aroma of familiar recipes weaving through the rooms create moments rich with emotion and nostalgia.

But apart from being a gateway to past memories, this time of togetherness is also a practical opportunity to consider the future—especially when it comes to estate planning. Yes, the topic might seem a tad uncomfortable, juxtaposing merriment with serious conversations, but it's one that can lead to peace of mind.

Adult Children: Questions for Parents

 

While gathered around holiday cheer, these questions can help understand and prepare for family wishes:

  • Do you have an up-to-date will or trust in place? Because knowing that their affairs are in order can save you from future confusion and legal headaches.
  • Who have you chosen to make financial and medical decisions if you’re unable to? Clarifying this ensures everyone's on the same page should decisions need to be made swiftly.
  • Have you shared your wishes for medical care and end-of-life planning? Discussing preferences helps align plans with their wishes, removing guesswork during emotionally charged times.
  • If something happened tomorrow, would we know where to find your important documents and accounts? Centralizing document locations is crucial for smooth transitions.
  • Are there heirlooms or traditions you’d like us to know the stories behind? Preserving these tales keeps family legacies alive for future generations.
  • Do you feel confident that the people you’ve chosen to handle your affairs are still the right ones? These choices should reflect the current context and relationships.

Parents: Questions for Adult Children

 

In turn, parents might ask:

  • Do you know where to find my important documents in case of an emergency? This ensures immediate access when needed.
  • Have you considered creating your own will or an estate plan? Encouraging early planning can ease future burdens.
  • If you received an inheritance tomorrow, would you know what to do with it — or who to turn to for help? Thinking ahead can prevent financial missteps.
  • Are there family keepsakes or traditions you’d be heartbroken not to have carried forward? Identifying these can guide which mementos are preserved.
  • If you had to step in to help us — financially or medically — what support would you need? Knowing available resources can guide assistance and ease transitions.

Starting the Conversation Gracefully

 

Consider bringing up these questions during a serene walk or a quiet moment, away from the bustling meal. This setting can make the conversation feel less formal and more like sharing confidences.

Here's a startling thought—over 50% of U.S. adults don’t have a will or estate plan in place according to a Caring's Wills Survey in 2025. Meanwhile, probate, without a clear estate plan, can consume 3–7% of an estate’s value, and drag on for a considerable time source. For families without a plan, 58% report disputes after a loved one’s passing source.

Estate planning isn't only about wealth—it's about control, clarity, care, efficiency, and legacy. When families approach this topic with empathy and transparency, it's not about the dollars, but cultivating peace and preserving values. The holidays might just be the perfect time to embrace this meaningful gift of love.

If you're feeling uncertain about where to begin, or wish to navigate these conversations with ease, reach out to a trusted advisor who can provide the guidance needed to make informed decisions. These crucial talks usher in clarity and safeguard what will one day be a part of your legacy.