Written By
Elizabeth Flavin Crawford, Partner | Chief Executive Officer
This Christmas, my extended family will gather in Jackson Hole, where my father was laid to rest three years ago. It’s our first time being there together since then. We’ll attend Christmas Eve mass at the church where he served as a deacon, celebrating what would have been his birthday, and I find myself thinking about what it means to honor the past while stepping fully into the present.
Life moves in cycles of gain and loss. Someone we love passes away. A baby is born. A marriage brings new faces to the table. The family circle contracts and expands, and with each change, we’re invited to reimagine how we spend our time together. Time—not money, not things, not even the perfect words—is the greatest treasure we have to offer one another.
The temptation, especially during holiday gatherings, is to slip into familiar grooves. We see each other often, so we rehash the same stories. We fall into old debates that no one really wants to have. We avoid certain topics or, conversely, can’t seem to talk about anything else. For families who live close to one another, this can feel especially tricky. How do you find something fresh to say to people you saw last Tuesday?
The answer isn’t to manufacture novelty. It’s to be intentional.
Intentionality means asking different questions. Instead of “How’s work?” try “What’s something you’re looking forward to?” Instead of revisiting old grievances, ask someone to share a story about a moment they felt proud this year. When a new family member joins through marriage or a child begins to form their own opinions, invite them into the narrative. Ask them what traditions they’d like to bring. Listen for what matters to them now, not just what mattered five years ago.
New traditions don’t have to be elaborate. They can be as simple as a walk together after dinner, a toast to someone who’s no longer at the table, or asking everyone to share one hope for the year ahead. What matters is that they create space for the family you are now, not just the family you were.
When we gather in Jackson Hole, we’ll be different people than we were three years ago. Some of us carry fresh grief. Others carry new joy. All of us carry the weight and gift of time that’s passed. We could spend our hours together dwelling on what’s missing or debating the same old points of contention. Or we could choose to build something new—to share stories that strengthen us, to laugh in ways that honor both the past and the present, to create memories that the youngest among us will carry forward.
The people we love won’t be here forever. Neither will we. That’s not a morbid thought—it’s a clarifying one. It reminds us that the time we have together, right now, in this particular configuration of souls around the table, is unrepeatable.
So this year, wherever you gather, be intentional. Step out of the old ruts. Welcome the new members with open curiosity. Honor those who are missing by living fully in their absence. Tell stories that matter. Ask questions that go deeper than small talk. Build traditions that reflect who you are now, together, in this beautiful and broken and ever-changing family you’ve been given.
Time is the gift. How we spend it is the legacy.
Disclaimer: The content in this article is provided for informational purposes only and should not be relied upon as financial planning recommendations or advice. Please seek personalized advice from qualified professionals regarding all personal finance matters.
