High achievers almost never say this out loud: sometimes you get everything you wanted, and it doesn't feel the way they expected. Not because something's wrong with their life, but because arriving was never going to do what we hoped it would do. This edition of Dear Kerry Ann features a letter from a middle-aged woman who achieved everything she set out to do, but wants to know why she feels flat.

Menopause is often discussed as a collection of symptoms to manage. But it can also be understood as a profound developmental transition, one that touches the body, brain, identity, relationships, culture, creativity, and our sense of who we are becoming. The menopause books on this list explore that fuller landscape, moving from science and medicine into lived experience, cultural narratives, fiction, and finally the deeper questions of meaning, power, and Elderhood.

"I'm at a crossroads" is what midlife professionals say when something new comes alive and their stable career suddenly feels less central. But a life that's outgrown its container is not the same as a life that needs to be turned upside down. Here's how to tell the difference, and how to take your new passion seriously without quitting your job.

What is a midlife awakening, and how do you know if you're having one? It's the quiet and disorienting sense that the life you built no longer fits the person you're becoming. Here's how to recognize it, and why it isn't the crisis you've been taught to fear.

“Should I change careers?” and “Who am I becoming?” are not the same question. Here’s which one to answer first — and how to begin.