It’s impossible to be in midlife and not wonder how you got there. It’s a question that inevitably comes with thinning hair and wrinkles that reveal passing time like tree rings. If you’re curious and bold, you will eventually ask the more important question: Where is my life headed, and how will I find joy, purpose, and meaning in the next chapter of life?
The truth is, I’m 62 and still trying to figure it out.
Right now, I am dipping my toes and surfboard into the warm Pacific Ocean as I spy a whale thrusting its way out of the water. I am at home in Baja, Mexico, which happens to be the home of the Modern Elder Academy (MEA), which I cofounded five years ago as the world’s first midlife wisdom school dedicated to helping midlifers reimagine and repurpose themselves.
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Less than an hour ago, I asked our latest cohort of wisdom seekers (a.k.a. our “compadres”) the same questions. They have come from all over the world to be here, and today was one of those magical days when smiles came easy and eyes opened wide as our midlifers realized they could shed old identities and become who they always wanted to be. That the best is yet to come. It’s a liberating feeling when you finally accept that you no longer have to define the second half of your life based on someone else’s definition of success—which also means you no longer have to define yourself by your achievements, image, status, or power.
Thousands of midlifers aged 28 to 88 (averaging 54) have walked through our doors (yes, we define midlife broadly). And every time someone makes this profound shift, it feels like we’re witnessing it for the first time. At MEA, we call this the “Baja aha” moment—a flash of clarity or insight that awakens the spirit to what’s possible.
As I smiled at the beauty of the day and hit the water with my surfboard, I still wondered how life had brought me to this moment.
I never expected to be a champion for midlife, or anything close to it. The truth is, in my late 30s, I dreaded the idea of midlife. It felt like such an emotionally dehydrated life stage, and if you survived it, all you had to look forward to were disease, decrepitude, and death. Like all good denialists, I pushed midlife (and aging) out of my mind and kept working, reaching, and attaining.
I started a boutique hotel company, Joie de Vivre, which I named to reflect our company’s mission to celebrate the joy of life. Poetically, it was also why I chose to sell the company after 24 years as CEO. I didn’t feel the joy anymore.
Compounding matters, I had just come out of the Great Recession, which was intensified by losing five midlife male friends to suicide, as well as having suicide ideation myself. I also had an unexpected near-death experience. During this period of intense reflection and struggle, I slowly woke up with a sense that something was missing from my life.
This ignited my curiosity about the purpose of midlife and how we could shift our mindsets to live happier and healthier lives. A seed was planted.
After selling my boutique hotel company, the three young founders of Airbnb asked me to be their in-house guide and mentor, which I happily did for the next seven years. Surprisingly, I also became their student, or “mentern.” Little did I know, this mutual arrangement would become one of MEA’s secrets to thriving in midlife: learning to marry wisdom and experience with curiosity and a beginner’s mind.
For many of us, midlife is when we begin to worry that our life isn’t turning out as expected. We may feel a sense of lost opportunity and frustrated longing. Often, we look in the mirror and see a stranger. Fortunately, it’s also when we begin to understand what is truly important and focus on recalibrating and designing the life we want to live. And once we settle into the transformative opportunity of midlife, something profound and beautiful awakens inside us.
Out of my discontent and dark night of the soul came curiosity and an inward search for deeper meaning. I began to wonder, what if midlife wasn’t a crisis but a “midlife calling,” or a “chrysalis,” a time of magical transformation?
From what I could see, midlifers weren’t seeking retreat or denial but relevance and purpose, which led me to ask MEA’s seminal question: How do we help people realize they have more choices in midlife than they even knew?
And, for that matter, where were all the champions of midlife?
As I saw it, higher education had been way too focused on the younger person, and we desperately needed a midlife pit stop. We fuel up at age 20 with all that knowledge in our heads and start driving our car of life. Around 50, we’re operating on fumes. That would have been fine a generation ago because we would have retired at 60 or 65.
But today, with the average life span rising and many bypassing the traditional retirement age, the conversation around aging is changing significantly. Unfortunately, our society offers little support and inspiration for the many transitions during these expanded years. It became evident to me that we not only needed a midlife pit stop and fuel-up, but a compass to help us determine our true north. We also needed a midlife pause to gather the wisdom, tools, and rituals to navigate—and celebrate—this sacred passage.
And thus, the Modern Elder Academy was born. My midlife crisis had transformed into my midlife calling: helping wisdom seekers (of all ages) discover a renewed sense of purpose in their lives.
As I look back on our first five years, I have always loved that our curriculum is based on “long-life learning,” creating a life that is as deep and meaningful as it is long. The beauty of this objective is that it is impossible to achieve without letting go of our egos, harnessing our wisdom and life experiences, and inviting in curiosity, awe, humor, joy, and a soulful spirit.
Simply put, it is in the journey of becoming where we discover the real magic of midlife.
When I step out of the Pacific Ocean, my dog Jamie is patiently waiting for me. In a few minutes, I will meet with our students again, which always surprises me in unexpected ways. The more I think about it, the more I realize that what brought me to this moment is the same thing that brought them here—the joy of discovering what’s next.
By the way, I didn’t catch a single wave today. But that’s all right. There’s always tomorrow.
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