national significance, including work at the Atlanta Olympics. When his own leadership team approached him about buying him out, he stepped aside completely, deliberately, so they could lead without his shadow. He was financially secure. And he was utterly unprepared for what came next. What Scot discovered was that financial freedom, while genuinely liberating, answered only the question of “Can I?” It said nothing about “What for? Today he works about twenty-five hours a week, selectively, on his own terms. “I never considered myself retired,” he told me. “I just stopped doing work that didn’t align with who I was becoming.” “The happiest retirees I interviewed were not those with the largest accounts. They were those who had a plan for how to live—not just how to pay for it.” Myth #3: Freedom without structure is bliss No more alarm clocks. No more packed calendars. Retirement promises a delicious erasure of obligation—and for the first few weeks, it often delivers. But here is what almost no one tells you: humans are wired for rhythm. We need ritual, routine, and a sense of forward motion. Without some scaffolding to the day, freedom can curdle into restlessness, then boredom, then something that quietly starts to look like depression. Janet Lowe taught elementary school and ESL for nearly four decades. Work was not just her job—it was her hobby, her community, her daily reason to get up. When she retired at sixty-four, she was euphoric. Within weeks, she was lost. “I thought I wanted endless freedom,” she told me, “but what I really needed was a reason to get up in the morning.” Janet rebuilt her life deliberately: a volunteer organization, painting classes, a walking club, regular “margarita outings” with friends. Structure, she discovered, didn’t limit her freedom—it gave her freedom meaning. The myth equates structure with constraint. The truth is, structure is the scaffolding that makes authentic freedom possible. The happiest retirees design their days with intention—not a rigid corporate schedule, but a gentle architecture of purpose, connection, and play. Your next chapter is yours to write The old story about retirement—that it’s a finish line, a retreat, an ending— was written in 1935, when the average American didn’t live much past sixty-five. Today, many of us will spend twenty to thirty years in this stage of life. That is too long to drift. Too long to be sustained by golf and vacations alone. Too long to leave to chance. The men and women I interviewed for this book—entrepreneurs, executives, educators, caregivers—did not stumble into fulfilling retirements. They designed them. They asked hard questions. They challenged the myths they’d inherited. They rebuilt their identities, curated their communities, and discovered that purpose, far from expiring at the end of a career, often deepens when the pressure of professional performance finally lifts. Rethinking retirement starts with a simple but radical act: deciding that this next chapter belongs entirely to you. Not to the financial plan. Not to the cultural script. Not to what “people like you” are supposed to do. To you—your curiosity, your values, your vision for a life that still matters. “Retirement isn’t about stepping away. It’s about stepping toward: toward joy, purpose, and the life you choose to create.” The door is waiting. Walk through it and see what’s on the other side. ANDI SIMON, PhD, is a corporate anthropologist, award-winning author, speaker, and host of the On the Brink with Andi Simon podcast. Simon helps individuals and organizations rethink change, culture, leadership, and the next stage of life with insight, empathy, and practical tools for transformation. Rethink Retirement: It’s Not the End—But the Beginning of What’s Next is available through Amazon, select independent bookstores, and at AndiSimon.com. Andi is a member of the Enterprising Women Advisory Board. enterprising Women 73
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