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There is a particular look people sometimes give when I tell them that I lead workshops on writing legacy letters. It is not unkind. But it is unmistakable. It is the look that suggests discomfort—an unspoken question hovering just beneath the surface: Why would anyone want to think about death before they have to? I understand the reaction. In many cultures, we are taught—implicitly and explicitly—that talking about endings is morbid, pessimistic, or even inviting misfortune

When I read Mitch Albom’s recently published novel Twice , I couldn’t stop thinking about how many of us long for do-overs in life—not so much to fix our mistakes, but to say the things we left unsaid. In the novel, Albom introduces us to Alfie Logan, a man with a secret power: he can rewind time to moments he has already lived and experience them again. When he says the wrong thing, or when life feels messy, Alfie resets and tries again. Each rewind creates new consequences,

In his 2025 memoir Born Lucky , journalist Leland Vittert shares that out of everything his father ever wrote, one column is remembered more than any other. Its headline was stark: “I’d give every asset I have if I could just have him back for one day.” The column wasn’t about regret. It focused on the questions his father never had the chance to ask his own dad-- how he fell in love, how he built his career, why he was so tough, and why he loved so deeply even though he rare