If you’ve been pondering the mysteries of midlife, you’re certainly not alone. As I consider the whole topic of midlife, one of the first things that arises is the question of when exactly does it begin?
It’s a phase that often arrives less like a sudden thunderclap and more like gentle (or sometimes not-so-gentle) music, with the volume dial steadily increasing until it can no longer be ignored.
When Midlife First Whispered
Looking back, the first whispers of my own midlife journey ironically began pretty young in my mid-to-late thirties. For years, I was convinced my life’s legacy would be played out as a professional musician. I poured my heart and soul into working in the industry, mastering my craft, playing gigs, and enjoying the performing arts in general.
But slowly, subtly, a different melody began to play in the background, hinting at a calling rooted in my interest in the philosophical and spiritual realms, fostered by my degree in East Asian studies from Columbia University.
The Pivotal Meeting That Changed Everything
When I met author Don Richard Riso in the late 1980s in New York City, it was a pivotal moment that completely rerouted my life’s GPS. After a couple of years of intellectual and deeply fulfilling conversations about all the sacred traditions of the world, I signed on as his assistant, embarking on a stimulating journey that has become my life’s work. It was at this point, my focus shifted from music to studying the Enneagram system of personality, and I’ve consistently found it to be an indispensable gauge of my own awareness. It keeps me tuned in to myself in order to be of better service to my community.
The initial ascent into my Enneagram career was an exhilarating climb up a very steep hill. I was writing books, teaching workshops all over the world, and working hand-in-glove with Don as a two-man band. This period culminated in the publication of The Wisdom of the Enneagram, a book whose enduring mark on people’s psychological and spiritual self-discovery remains a high point of my life. I found myself on a global platform, sharing the Enneagram with diverse groups and organizations. It was also my frenetic prelude prior to midlife.
Loss and the Question: “What’s Next?”
The landscape shifted dramatically in 2012 with Don’s peaceful passing after a battle with cancer. Being present with him during his death was profound, and it plunged me headfirst into the colossal question: “What’s next?” Our collaboration had been so intimate and intertwined that his absence created a significant void in my life.
The following years were a whirlwind of reorganization both for those involved in Don’s original organization and, most certainly, for me. Slowly but surely, I began to build a new chapter centered around my own writings and offerings.
During this time, I truly felt the waves of midlife. Launching a new entrepreneurial venture while my internal compass was yearning to slow down was, to put it mildly, a bit of a comedic struggle. I had to globe-trot to keep teaching and stay true to my life’s purpose while simultaneously dreaming of enjoying a spiritual retreat in nature with an all-inclusive Michelin 5-star restaurant – and naps! There was no neat retirement package for me, no gold watch at the end of a long, demanding career.
I had to find an entirely new way to navigate these middle years.
Three Essential Qualities for Midlife
As I reflect on the lessons of my own journey, three qualities emerge as absolutely indispensable for navigating midlife: adaptation, discernment, and acceptance. While these are valuable at any stage, they become acutely necessary as we open into our later years.
Adaptation has been a recurring theme. After years of working with Don and the Enneagram Institute, I had to find new pathways forward.
Adaptation wasn’t just about external changes; it also involved learning to honor my body’s natural wish to slow down. I’d been going at a furious pace, but in September 2019, on a date forever etched in my memory (September 11th, no less), I woke up in a Paris hotel room with chest pain that quickly spread to my left arm. Medical savvy in me knew this was trouble. Thanks to quick thinking and some limited French, I was whisked to a hospital where they saved my life, detecting blockages in my heart and inserting two stents. Clearly, barreling along as I had been with constant travel and relentless hours was no longer sustainable, and this was a wake-up call.
How could I continue my work while taking better care of myself?
COVID, ironically, provided the answer, giving me a much-needed pause to reformat my life. The isolation required in those early days of the epidemic forced me to completely reimagine my work, shifting from in-person workshops to the brave new world of online programs – a concept almost unheard of for me before 2020. Even after the toughest years of COVID I continued to keep a slower pace and to do most of my teaching through online programs with occasional trips for in-person workshops and retreats.
Then, just last year, returning from Asia, I was hit with another intense sickness, ending up in the hospital in septic shock. The doctors informed me that recovery from septic shock is often less probable than from a heart attack, so I consider myself incredibly fortunate to be here. This experience brought yet another wave of adaptation, particularly regarding my stamina, which had significantly diminished over the previous year. It has been frustrating to not be able to meet the many demands on my time, energy, and attention, but realism had to prevail. My body was in healing mode. This forced me to find a new balance, a key aspect and the most notable adaptation in midlife for most of us: how do we allocate our time and attention to the different parts of our lives?
Choosing What Matters Most
This leads us to discernment. Now that my stamina is gradually returning from the sepsis, I’m not keen on jumping right back into my old frantic pace. Online teaching is excellent, but I value live in-person interactions and workshops. Yes, I have exciting projects on the horizon, including a new book on creativity and the Enneagram with my colleague, Catherine Bell, and another book about the Enneagram’s Points and Essence. I am more selective about when I say “yes” and what I commit myself to.
Discernment and adaptation are a dynamic duo, fostering a growing pragmatism about where I am in life. Like many of us, I’ve developed a multitude of talents and capacities, and I know I have much to offer others. But it’s also organically intelligent to use this period of life for the contemplation and maturation of our own being. This is the time in life for cultivating wisdom.
Finally, There’s Acceptance.
It’s not always easy to accept that my stamina and energy levels aren’t what they were 20 years ago. It’s a bit like admitting that my hair might have a few more “distinguished” silver strands than it used to. It’s not easy to accept the limitations imposed by physical challenges or that some people might be frustrated because they expect “that guy from 20 years ago.” However, a profound, heartfelt appreciation can blossom as we acknowledge the people and situations of our lives as they are. Acceptance opens us to a greater appreciation of life’s beauty and of the many possibilities now open to us.
The Adventure of Inner Riches
I’ll never forget a conversation with Don Riso near the end of his life. He was largely incapacitated by his illness, but his spirit was vibrant. Lying in bed, he recounted our escapades, like a time a few years earlier when I helped him climb the stairs of the Acropolis in Athens – something he had always wanted to do. It was difficult for him: the illness had already weakened his body. Yet he described that day as “such an adventure” and “amazing.” Then he looked at me, a mischievous twinkle in his eye, and said, “You know what? Now it’s an adventure for me to figure out how to turn over in bed without a lot of pain, but it’s just as interesting!” That landed with me. Hard.
What Don was getting at, and what I now deeply understand, is this: As we age, the riches of our inner life, all that we have learned and gathered from our journey through this world, begin to come into a richer and deeper maturation. Some of our worldly capacities might diminish, yes, but that in no way signals the end of our journey, nor does it diminish our opportunities to discover joy, appreciate life, cultivate creativity, or contribute something meaningful to the world.
Even now, approaching 70, I don’t feel that my learning about my inner work is complete – nor is my exploration of the Enneagram, for that matter. Unveiling new things about myself, my life, and humanity is far from over. While I am purposely slowing down my pace, I’ve also found a long and gradual process of polishing and refining my teachings. I am learning how to better balance the mind, body, and heart using the Enneagram and to bring this balance and learning into my work with my students. Sometimes, in fewer words and less time, I can convey what I’m here to share.
I can’t take all the credit; it is part of the natural development of the human soul, coupled with messages passed down from my honored teachers from a wide range of religious traditions, sacred texts, and psychological schools. As I live the lessons I have learned, I see the truth of the teachings I have received within my own experience, and I have learned how to support others in doing the same.
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If you’re curious about how the Enneagram can help you compose your future to connect more fully with yourself, your loved ones, and your community, I would be delighted for you to join me for my upcoming workshop in the Santa Fe desert, where we will learn to truly inhabit our own skin, dance with the life we’re given, and cherish those who are called into our circle.
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