The Gift That Keeps on Giving: Starting Estate Planning Conversations Over the Holidays

The holidays bring families together like no other time of year. Between passing the mashed potatoes and sharing stories, these gatherings create natural opportunities for some of life’s most important conversations—including discussions about the future that many families tend to avoid.

If you've already taken steps to protect your family through estate planning, the holidays offer the perfect moment to encourage your loved ones to do the same. You understand firsthand the peace of mind that comes with having a solid plan in place. Now you can share that gift with others.

Making It Natural, Not Awkward

The key to successful holiday conversations about estate planning isn't diving straight into wills and trusts over dessert. Instead, look for organic moments. When someone mentions a friend's recent health scare or a neighbor's family dispute, that's your opening to gently ask, "Have you thought about what would happen if something unexpected occurred in your family?"

You might share your own experience: "Getting our estate plan done was such a relief. It felt good knowing everything was handled." Sometimes hearing that someone they trust has already taken these steps makes the idea less intimidating for others.

Questions That Open Doors

Consider asking gentle questions that get people thinking: "Do your kids know where your important documents are?" or "Have you updated your beneficiaries lately?" These aren't confrontational—they're caring inquiries that plant seeds.

For aging parents, you might approach it differently: "We've been thinking about our own plans lately. Have you and Dad had a chance to review yours recently?" This positions you as someone who's also navigating these decisions, not lecturing from a distance.

The Ripple Effect

When you encourage family members to create their own estate plans, you're giving them a gift that extends far beyond any physical present. You're offering them the same security and peace of mind you've experienced. And you're potentially preventing the kind of family conflicts and legal complications that can tear families apart during already difficult times.

This holiday season, consider how your own positive experience with estate planning can become a conversation starter that truly makes a difference in your loved ones' lives. Sometimes the most meaningful gifts are the ones that protect the people we care about most.