Most families reserve the holiday season for celebrating with family and taking a break from the daily grind. It’s a time when loved ones gather, share meals, and catch up on the events of the past year. But amid the warmth and connection—especially for older family members—one question quietly lingers: Is this the right time to talk about estate planning?

All Your Family in One Place

For some, the answer is a clear yes. The holidays offer a rare chance to have important conversations while the entire family is in one place. Coordinating schedules can be a challenge during the rest of the year, especially if family members live far apart. When everyone is together, it can be the ideal setting to discuss wills, healthcare directives, and long-term wishes. Being in a relaxed and familiar environment can also make it easier to have these serious conversations.

Additionally, the emotional closeness of the season may encourage more open and thoughtful conversations. Framing estate planning as a way to protect and care for loved ones—not just a legal formality—can make the topic feel less daunting. It’s not about fear or control; it’s about peace of mind and clarity for the future.

Don’t Spoil the Holiday Spirit

However, timing is everything. Some family members will not appreciate being asked to have these serious conversations while they’re trying to enjoy the holidays. Estate planning discussions can stir up difficult emotions or even family tension, particularly if there are unresolved issues or differing expectations. If not handled carefully, these conversations can ruin the warmth and closeness of your holiday gathering.

Should You Bring Up Estate Planning This Holiday Season?

So, should you do it? That depends. If your family has good communication and you approach the topic with sensitivity, the holidays can be a smart time to lay the groundwork for estate planning. It doesn’t have to be a full-blown meeting. Just starting the conversation can be a pivotal step.

On the other hand, if emotions tend to run high during the holidays, it might be better to wait. You can use the time to observe, reflect, and plan for a future conversation when the setting is calmer and more private.

When you’re reading to discuss your estate and your family’s future, reach out to Feniger, Uliasz & Stacey for assistance and advice. Our attorneys will work with you to craft an estate plan that ensures your wishes are honored. Contact us today to speak with a member of our team and learn more about our services.