Gathering Around the Table: Estate Planning During the Holidays
Lori Woodward | Dec 09 2025 16:00

The holidays bring the rare joy of gathering family from multiple generations in one place. These cherished moments, filled with shared meals, stories, and traditions, offer more than just connection — they present an invaluable chance to discuss the future together.

Nearly 55% of U.S. adults don’t have a will or estate plan. Involving your family in this conversation can prevent the 58% of disputes that arise posthumously due to lack of planning. Estate planning isn't only for the wealthy; it’s about control, clarity, care, efficiency, and legacy.

The Perfect Time for a Conversation

The holidays provide a unique opportunity to discuss estate planning. While the topic may be uncomfortable, think of it as a gift of clarity and love, saving your family from future confusion and legal battles.

Questions to Ask Each Other

Engaging in a calm, empathetic dialogue strengthens family bonds. Here are some key questions you can explore together:

Questions Adult Children Can Ask Parents:

  • 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 Adult Children:

  • 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?

Timing and Setting

Consider bringing up these discussions during calm moments — perhaps during a walk or while having coffee, rather than over the main meal.

Remember, initiating these conversations now can prevent emotional and financial distress later. Estate planning is a gift of love and clarity. If you're unsure where to begin or need guidance, consider reaching out to a trusted advisor. Let this holiday season be the start of securing peace of mind for your family’s future.