John E. Chapman Chief Executive Officer“Home is where you are,” the saying goes. But for many families, there is also a place that draws everyone together, a setting where you can step away from the everyday and remember what matters most. For some, it is the cabin, the lake, the beach, or the mountains. For our family, after much research and travel, that place became St. Thomas.
More than just a beautiful destination, St. Thomas reflects our multigenerational family in many ways, with something for each of us. It has become the backdrop for countless memories and conversations, a place to gather, share stories, and carry forward the values of our family from one generation to the next.
Finding our place
Chicago is home, but winters here are unforgivingly cold. Growing up, we had a tradition of “getting out of dodge” in January, February, or March, chasing warmth and sunshine. Years ago, we decided to look for a more permanent winter retreat, a place we could return to consistently and call our own.
After several seasons of island hopping, we found our spot. With its Afro-Caribbean culture, incredible food and music, and its endless water and sky, we collectively fell in love with St. Thomas. Each year now begins with the familiar question of whether our plane will escape Chicago’s latest snowstorm. Delays that once felt stressful have turned into a collection of family stories we laugh about later, proof that even small inconveniences become part of the shared narrative over time.
Touching down
Landing in St. Thomas, the first thing you notice is the warmth. Temperatures in the 80s and strong tropical sunshine are a welcome contrast to a Midwest polar vortex, a reminder that you are not in your normal routine anymore. The blues and turquoise of the water and the dramatic landscape make it clear you are somewhere set apart.
What matters most, though, is what this difference in place creates for our family. A familiar home away from home gives us relaxed, uninterrupted time to catch up, recharge, and be fully present with one another. The pace slows. Conversations lengthen. There is room to both revisit old stories and create new ones.
A once-in-a-lifetime winter
This past winter stands out as a once-in-a-lifetime experience. We had four generations together, from ten months old to eighty years. The stories we told and the time we shared at this particular stage of life felt rare and precious. This is where conversation naturally shifts from the mundane to the meaningful, where we can play in the sand, ride in the boat, or simply do nothing at all, together. The shared experience becomes another thread that binds us.
We also added a new tradition: each day was dedicated to a different family member. Everyone wrote a note highlighting their favorite qualities about that person. The result was simple, intentional encouragement. We reflected on the giving we had done together in 2025 and made plans for 2026. There were serious, heartfelt moments and plenty of lighthearted ones, often courtesy of the toddlers, yet all of it contributed to a deeper sense of connection and purpose.
The value of a “happy place.”
In our work with families of wealth, we often see how intentional gathering, whether at a family retreat, a shared vacation home, or a favorite destination, can strengthen the bonds that sustain a family across generations. These shared experiences help build the trust, communication, and alignment of values that support effective multigenerational wealth stewardship and decision making.
None of us knows exactly what the future holds, but we are deeply grateful for the times we have had together in this happy place. It has become one of the ways we live out our family’s story in real time.
What family places and traditions are meaningful to you, and how are they shaping the legacy you hope to pass on?
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