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.

