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.

Everything perfect. Everything planned with love.

I showered, put on comfortable travel clothes—black leggings, a soft Northwestern sweatshirt, the running shoes I use for my four-mile jogs along the lakefront—and double-checked my suitcase one more time. Passport. Wallet. Printed confirmations even though everything is in an app now. My cardiology brain doesn’t trust a single point of failure.

At 5:00 a.m., a black sedan from a local car service pulled up in front of my brownstone. The driver loaded 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 Willis Tower and John Hancock Building just silhouettes against a still-dark sky. Even after all these years, that drive still makes me feel lucky to have lived my whole life in this city.