Jessica Christy
Estate Planning: A Holiday Table Conversation
Nov 24 2025 20:00
As the holiday season approaches, families gather around the dinner table, a space filled with laughter, stories, and cherished traditions. These moments are more than just festive, they represent the unique opportunity for multiple generations to converge in one place.
Amidst this warmth, there's an often-overlooked subject ripe for discussion: estate planning. While it might not be the easiest topic, having these conversations can lead to peace of mind and clarity for everyone involved.
Why the Holidays Present an Ideal Opportunity
During the holidays, families are together, creating the perfect environment to discuss future plans. These discussions need not be formal or intrusive. They can begin casually during a walk or a quiet moment after a meal.
Key Questions for Family Conversations
Questions adult children can ask their 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 their 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?
Approach the Topic with Empathy and Clarity
These discussions should be approached with empathy and a focus on clarity. The goal is to ensure everyone knows and respects each other's wishes. Bringing these subjects up with compassion can ease the discomfort often associated with them.
The Gift of Preparedness
Estate planning is not merely a legal exercise; it's about safeguarding your family's future, reducing risks of disputes, and ensuring a legacy of love. As you gather with loved ones this holiday season, consider the impact of these conversations. If you're unsure where to start, reaching out to a trusted advisor can be an empowering first step.
Ready to discuss your estate plan? Contact us for personalized guidance to navigate these essential conversations.

