Encore

Even the etymology of the word retire drops a clue as to why people don’t like it. In Middle French, retirer meant to withdraw or pull back. Modern definitions continue this theme of retreating, withdrawing, or receding. Unfortunately, the word gives us no indication of forward motion or expansion into something new, leaving those on this precipice in quite an existential quagmire.

Thanks to my fifteen years of guiding intense professionals as they plan for life after their careers, I am all too familiar with the squirming discomfort they often feel about the topic of their own retirement. In fact, the closer it gets, the more concerning it becomes. It is a bit like being marched toward an abyss that is somehow supposed to seem appealing. For some, the idea of change is welcome, but the absence of a plan is disturbing. For others, retirement equates with an appalling loss of who they are and what they love to do. This condition is made even worse by the celebratory attitude surrounding them—everyone else is ready to break out the champagne while the soon-to-be “retiree” is, at best, feeling unsettled and, at worst, feeling rather terrified. And then comes the relentless but confounding question: “What are you going to do?” All too often, my clients (who are accustomed to having answers) are utterly stumped.

I’ve Done Everything Right, So Why Do I Feel Lost? 

The odyssey of work doesn’t go on forever. Toward the end of even the most epic career, there comes a time when the hero must set sights on their inevitable landing. I have a stark memory of one of our early clients, Jim, who embodied this contradiction well. At the time, he was widely known and respected in his field as one of the greats. I felt privileged even to meet him, much less to guide him in his thinking about life after retirement. He was physically imposing, quietly powerful, humble in his bearing. When we asked him what brought him to us, he answered in a low voice. “Well, I feel like I’m running toward the edge of a cliff. I have no idea what I will do or who I will be in sixty days.”

I was struck by the paradox before me. Here was a capable and accomplished leader who had excelled at the highest levels. In his own words, he was still at the top of his game. He was making the choice to retire because it was the right thing to do for his organization and for his younger colleagues, who were ready to step up to the opportunities his exit would create. His retirement was an intentional and selfless act. He had been a diligent saver and felt confident about his financial security. And yet, despite his volition, ability, and track records of success, here he sat before us without the first idea what the rest of his life would be about. “I’m terrified, if you want the truth,” he said.