(Photo courtesy of Suzanne D. Williams)
Inspired by Chip Conley, the visionary founder of the Modern Elder Academy, I’ve been thinking a lot about the journey of midlife because many of those issues can live beyond that period—specifically, the part where you start shedding the old skin of who you thought you were supposed to be and embrace a more authentic version of yourself. Conley, who describes his mission as helping people transition from their “first adulthood” to a “second adulthood,” offers a roadmap for what he calls the “midlife chrysalis”—a process of transformation that’s as messy as it is necessary. I am living proof that what Conley espouses lives on and is always available and as valuable as ever as we continue to age.
Midlife is a peculiar place to find yourself. You’ve spent decades following the rules, climbing the ladder, and trying to fit into a neat little box that society insists is the path to happiness and success. But somewhere along the way, a quiet—or maybe not so quiet—voice starts whispering (or yelling) in your ear: “Is this really it?” If you’re lucky, this voice gets louder and louder until one day you realize it’s not just a whisper anymore; it’s a full-blown call to action. And that action? Saying “f*** off” to the narrow paths that have constrained you.
The Chrysalis of Midlife: Breaking Out of the Cocoon
As mentioned, Conley uses the concept of the chrysalis to typify the challenges and opportunities that present themselves in midlife. Think of midlife as a kind of chrysalis stage, like that awkward, gooey period when a caterpillar turns into a butterfly. It’s messy, it’s confusing, and it’s uncomfortable as hell. But it’s also the process of transformation, of disassembling the parts of your life that no longer serve you and rebuilding something that feels more authentic. This disassembling isn’t about destruction for destruction’s sake; it’s about clearing away the clutter so you can see what really matters.
Richard Rohr, a Franciscan friar and spiritual writer, describes this process as “Order, Disorder, Reorder.” In the first half of life, we live in “Order”—we follow the rules, we build careers, we raise families, and we try to be good citizens. But then, something shifts. Maybe it’s a job loss, a divorce, a loss of relevance, or just the creeping realization that you’ve been living someone else’s idea of a good life. That’s when “Disorder” kicks in. Everything falls apart, and it feels like you’re standing naked in the world with nothing to hold onto.
But here’s the secret: Disorder is where the magic happens. It’s where you get to strip away the layers of societal expectations and get real with yourself about what you actually want. It’s where you find the courage to say “f*** off” to all the things that have been holding you back.
Real-Life Examples: The Art of Saying “F*** Off”
Take Steve Jobs, for instance. In 1985, he was unceremoniously fired from Apple, the company he co-founded. Talk about Disorder! But instead of giving up, Jobs used this period of his life to reevaluate his priorities. He founded NeXT, bought Pixar, and eventually returned to Apple to lead one of the most remarkable corporate turnarounds in history. Jobs could have stayed down, but instead, he said “f*** off” to the constraints of his past and embraced his autonomy. This reinvention wasn’t just about career success; it was about redefining who he was and what he stood for.
Or consider comedian George Carlin, who started his career as a clean-cut, mainstream performer but found himself increasingly disillusioned with the entertainment industry’s expectations. In the 1970s, Carlin went through his own chrysalis phase, reinventing himself as a countercultural icon known for his sharp, biting humor and willingness to say what everyone else was too scared to voice. Carlin’s transformation wasn’t just about his career—it was about fully stepping into who he was meant to be, and saying “f*** off” to anyone who didn’t like it. He didn’t just change his act; he changed his life.
The Thirst for Reorder: A Fresh Start in a Chaotic World
In the broader context, we’ve all felt the societal Disorder of the past few years. Between a global pandemic, political turmoil, and a constant barrage of bad news, it’s been easy to feel like the world is spinning out of control. But maybe that’s not such a bad thing. Maybe we need to go through this collective Disorder to create a Reorder that’s fresh and future-oriented.
Think about it: The pandemic forced many of us to rethink how we live and work. Suddenly, the idea of working from home, once a pipe dream for many, became the norm. People started questioning whether the 9-to-5 grind was really necessary, and whether spending more time with family, pursuing creative passions, or simply enjoying life might be a better way to live. This is the Reorder phase—a chance to rebuild not just our individual lives, but our society, in a way that feels more aligned with who we are and what we value. It’s about creating a future that’s less about following narrow paths and more about embracing autonomy, creativity, and joy.
Embracing Your Autonomy: Naked and Unafraid
Standing naked in the world—metaphorically speaking, of course—can be terrifying. But it’s also liberating. Midlife is your chance to shed the expectations that have been weighing you down and step into a new version of yourself that’s more authentic, more autonomous, and a hell of a lot happier.
So, how do you do it? Start by listening to that little voice inside you that’s been whispering all along. What does it want? What have you been putting off because it didn’t fit into the neat little box of your life? What are you ready to say “f*** off” to?
Remember, the chrysalis stage is messy. But it’s also necessary. And on the other side of it? That’s where the butterflies live. That’s where you get to reorder your life in a way that feels fresh, future-oriented, and fully, unapologetically you.
The Courage to Reorder: Inspired by Chip Conley
Chip Conley has shown us that midlife doesn’t have to be a crisis—it can be a renaissance. It’s about taking all the wisdom you’ve accumulated, mixing it with a healthy dose of courage, and stepping boldly into the second half of your life with a renewed sense of purpose. It’s about realizing that the rules that served you in the first half of your life might not apply anymore, and that’s okay. In fact, it’s more than okay—it’s an opportunity to create something entirely new.
So, go ahead—embrace the mess, embrace the uncertainty, and embrace your autonomy. The world is waiting for you to break free. Because in the end, the greatest gift you can give yourself in midlife is the freedom to live on your own terms, naked and unafraid. And thank you, Chip Conley!
Bob Fagan has just published “The Little Book of Questions That Matter — A Lifetime Companion For Transforming Your Life.” It is available on Amazon.
