I bought plane tickets for the whole family, but at the airport my daughter-in-law gently told me they had given my seat to her own mother because the kids feel ‘closer to her,’ and my son quietly agreed. I froze for a moment, then smiled and walked away without raising my voice. One minute later, after I’d calmed myself, I changed the entire $47,000 Hawaii vacation with a single polite phone call and quietly rearranged my $5.8 million estate in a way no one expected.

about oceanfront versus partial ocean view, and talked to three different concierges on Maui before I was satisfied.

In the end, I booked us into an upscale resort in Wailea—oceanfront suites, on-site kids’ club, lazy river, the kind of place where families from all over the United States fly in with matching Lululemon luggage and sunhats that say “Mama” in cursive. I arranged luau reservations, snorkeling trips, a helicopter tour of the island, and a special day trip along the Road to Hana.

Ten days of memory-making with the people I loved most.

ded my suitcase into the trunk while I locked the front door of my house that I’d bought years ago when the hospital bonuses were coming in strong and the Chicago housing market was still forgiving.

We drove down Lake Shore Drive toward O’Hare International Airport, the lights of the Chicago skyline shimmering over Lake Michigan, the