Holiday Conversations That Lead to Better Planning

This holiday season, I’ll be gathering with my sisters and our families for Thanksgiving and Christmas. Both celebrations will include my 85-year-old mother. During a recent visit, I asked her a question that has since stayed with me: “What does a good day look like for you?”

She paused, thought for a moment, and said, “A good day for me includes sitting in the sun and enjoying the colors of the trees,” then added with a smile, “and being with you.”

Her answer was simple yet profound. It reminded me how crucial it is to understand what truly matters to our loved ones as they age. That one question opened the door to a deeper understanding of her wishes and allowed me to see how thoughtful planning could help her experience more of those “good days.”

Start the Dialogue This Holiday Season

The holidays are one of the rare times multiple generations gather under one roof, making it a perfect opportunity to start meaningful conversations about the future.

These discussions can feel delicate. Seniors may hesitate to share their concerns, or families might avoid the topic, thinking, “It’s not the right time.” The truth is, there’s never a perfect time—but moments of love and connection often provide the best opportunity.

If you’re unsure how to begin, consider asking:

• “What brings you joy in your day-to-day life?”

• “What does peace of mind look like for you?

• “How can we, as a family, support you better?”

Listening with an open heart can reveal what matters most to your loved ones, laying the foundation for planning together.