Speaking with a friend who’s nearing retirement, I asked how he was feeling about it. He said he’d looked forward to retirement for most of his working life—but now that it was close, his feelings had become more complicated. “At the same time I’m looking forward to it, I’m dreading it.” Why Retirement Feels So Different Than Expected The closer retirement gets, the less it’s about how you’ll fill your days and the more it becomes a deeper question: Who will I be when I stop working? That uncertainty dulls the excitement. Concerns about how to occupy your time take a back seat to something more fundamental—your sense of identity.

Most of us don’t realize the moment when life isn’t enough—it just begins as a quiet feeling something is missing. What happens when the life you built isn’t enough? For many people—especially later in life—that question doesn’t arrive gently. It shows up as a persistent dissatisfaction, or a deeper, harder-to-name unhappiness. What I’ve come to see is that this feeling often comes from a single, invisible source: living on the surface of our own lives, without even realizing it. It’s not that they’ve decided to live on the surface, or even know that’s where they’re living, they just aren’t familiar with the different purposes of the early part of life,

Over the years, I’ve coached a number of clients as they approached retirement. In almost every case there’s a period when the person about to retire freaks out a bit. Isn’t it ironic that there’s so much anxiety around retirement, a time of life we’ve been taught to look forward to? I’ve become convinced the primary reason for this freak-out has to do with just how much our identities (who we believe we are, and who we’d like others to believe we are) are shaped by what we do. For a majority of us, our sense of worthiness is inextricably tied to our profession. This sense of identity is essentially