The Luckiest, felt a bit like sitting down with a friend over coffee — the kind of conversation where someone finally stops pretending they have it all together and just tells the truth. It’s a story about ambition, motherhood, marriage, loss, and the long, slow work of rediscovering who you are after life knocks you sideways.
Kelly opens up about the many versions of herself — the young woman chasing Broadway dreams in New York, the wife of a rising star, the mother caring for a medically fragile child, the woman grieving an unimaginable loss, and, eventually, the person learning how to live again. What struck me most wasn’t just her honesty, but her ability to find meaning and even humor in the middle of heartbreak. She doesn’t sugarcoat anything, but she also doesn’t wallow. There’s this grounded resilience in her voice — a kind of steady, lived-in wisdom that comes from someone who’s been through the fire and made peace with the scars.
The theme of luck runs through the whole book, and it’s fascinating how Kelly plays with it. She doesn’t treat luck as something shiny or simple. Instead, it’s messy — sometimes cruel, sometimes kind, often both at once.
What I loved most was her reflection on identity. As a reader, I felt seen in her wrestling with all the different versions of herself — the performer, the caregiver, the woman trying to be more than her labels. The “nesting doll” metaphor — that we carry all our earlier selves inside us — really stayed with me. It’s such a gentle reminder that growth doesn’t mean erasing who we were, just learning to hold all those versions with compassion.
This isn’t a light read. There are moments that are heartbreaking, especially when she writes about her daughter, Adelaide. But there’s also an incredible tenderness to it — not just sorrow, but love, humor, and gratitude threaded through every chapter. By the end, I didn’t feel sad so much as grounded.
If you’ve ever had to start over, if you’ve ever wondered how to rebuild after loss or redefine what “lucky” even means, this book will speak to you. The Luckiest doesn’t promise easy answers — instead, it gives you a companion for the hard questions.