Mom, I think it’s best if you don’t join us for the trip to Silver Palm Resort next month. Amanda’s parents are coming and there’s just not enough room for everyone. I hope you understand.

I stared at my daughter Claire’s message, the blue light painting the framed photos on my nightstand—the one of her in a cap and gown at Northwestern, the one of her as a gap‑toothed second‑grader holding a softball bat almost bigger than she was.

“Not enough room” at Silver Palm. The same Silver Palm Resort with six oceanfront restaurants, three infinity pools, a kids’ club, a spa that had been featured in Travel + Leisure, and 312 luxury suites. The Silver Palm Resort on the tiny Caribbean island of St. Celeste, where American families from Chicago to Dallas to New York flew in for “once‑in‑a‑lifetime” getaways.

The same resort I quietly bought four years earlier after an investment in a small medical software startup had exploded far beyond anyone’s expectations.