The OG Midlife Crisis
Illustration: Gustave Doré, 1857
I have yet to meet a fellow traveler on this journey of life who has not found themselves lost at some point and wondering how they got there.
Once as a proud young man, I teased an older friend about his “advanced age.” He jabbed back: “Better to be forty-five and alive than twenty-two and through.”
His stinging retort rebukes a society that worships youth over experience. I used to resent the remark; now I resemble it. With adequate time to reflect and multiple life challenges overcome, I have learned to embrace its hidden wisdom: sooner or later, we all experience disillusionment—a failed romance, lost job, climate anxiety, you name it. The question is whether such setbacks derail us or propel us in exciting new directions.
When I was twenty-two, fresh out of Georgetown University with a degree in Economics, I landed a position in a competitive management training program that put me on the fast track to the C-suite. Every day, I’d commute from Jersey to Midtown to start my climb up the corporate ladder. Some weeks I would work up to seventy hours with single-minded devotion. One day, our Chief Legal Officer handed me a five-hundred page deposition and asked for my analysis. Wanting to impress him, I read through the War-and-Peace-sized document and returned a thorough breakdown in two days, which he said was as good as any he had read from his staff of corporate lawyers.
Those were the sort of “atta boy” encouragements that kept me going and signaled that I was on my way to corporate stardom! But in my quieter moments, I knew something was off.
When the top leaders of our massive corporation pitched possible career tracks to us, only two of the forty-plus career ladders held any appeal to me. While I may have been succeeding at work, I could feel my enthusiasm for the corporate world waning. I had recently led a spiritual retreat of peers at my local church and experienced a deep sense of fulfillment that was eluding me in the business world. During the three-day retreat, my friends and I explored what held ultimate meaning and purpose in our respective lives. This is what’s known as “pastoral work”—and I recognized that I had a natural gift for it.
Problem was, as far as I knew, only ordained ministers did this kind of work for a living. And for Catholics like me, that meant giving up my dream of starting a family. So I redoubled my efforts in corporate America, chasing status, power, and money even more vigorously than before.
I landed a fun, people-focused position in human resources, where I had a bird’s-eye-view on positions with the most earning potential. After about three years of late nights and long hours, I was offered what appeared to be a golden ticket. The leader of a new contracting area in the company—where contractors started at $250,000—loved the work I did staffing his area and invited me to join their division. Though I had misgivings about some of their hiring practices, I was too starry-eyed to object. Within weeks on the job, I was slicking my hair back full Gordon Gecko, hitting the weights hard at the gym, and living in a tony new flat on the Upper East Side. This was the new me, and I was going to make it work!
But life had other plans. A company car, make-your-friends-envious bachelor pad, and money to burn did not make up for my growing dis-ease at work. Long hours of work and loyalty were repaid with a toxic workplace run on shame, fear, and very little sleep. Regularly, our boss would remark, if I put in less than a twelve-hour day, that “there was still a tremendous amount of work to be done.” I was tired of working for someone who cut corners, bullied staff, and directed us to strong-arm clients into egregiously one-sided deals—or else. Realizing he was asking me to sacrifice my integrity in order to advance, I knew that I needed to leave not just this organization but the whole financial industry. I wanted a job I would love to do rather than loathe to do.
To create some space to clear my head, I flew to visit my sister at school in Florida. On my last day there, I went to church with her and met her campus minister, a person who serves the spiritual needs of college students. We hit it off and he even offered me a job running retreats! Naturally, I said yes, and started making plans to start helping people instead of swindling them. It all seemed too good to be true.
And it was. My job offer was rescinded a few weeks later due to a hiring freeze. Disappointed as I was, I could now see a way to do pastoral work and have a family.
I applied to one opportunity after another only to get an equal number of rejections. Many positions required a master’s degree in theology and ministry, so I did a nationwide search for relevant degree programs. Then one day I had lunch with a friend of my sister’s who knew that I had an interest in campus ministry. I told her the whole story and watched as a smile spread across her face. She said she administered a scholarship program that paid full tuition for students pursuing a graduate degree in theology and ministry in exchange for a few years of service. I could hardly believe my luck!
I applied to the program at Boston College that day. A month later, I learned I had landed the full scholarship. My new path was clear and I was ecstatic! Relieved at last to be exiting a soul-crushing job, I gave my two-week notice at work and began preparing myself for the work I was born to do.
* * *
While my crisis came in my twenties, you can lose your way at any point of the journey. Martha Beck, in her illuminating guide for the perplexed, The Way of Integrity, argues that the notion of a midlife crisis dates back to Dante’s Divine Comedy, which begins with him “midway upon the journey of life . . . within a forest dark.” Dante wrote his epic over seven hundred years ago. It seems that human nature changes rather slowly, if at all!
If you, too, feel you’ve strayed from your life’s path, take solace. I have yet to meet a fellow traveler on this journey of life who has not found themselves lost at some point and wondering how they got there.
While it may not be readily apparent, midlife is a golden opportunity to transform your life to be happier, healthier, and more aligned with who you most want to become. These three resources offer hope, consolation, and guidance for those of us wandering in Dante’s footsteps.
For those who could use a new view of midlife . . .
Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age by Chip Conley
Taking a holistic approach—mind, body, heart, soul, and spirit—Conley offers practical tips for embracing the unique gifts of midlife, the most salient being a sense of perspective born of experience and hard-earned wisdom. Chip Conley’s celebrates the “atrium of midlife” as a “chrysalis, not a crisis.”
For those who prefer a more intellectual take. . .
Midlife: A Philosophical Guide by Kieran Setiya
Setiya’s well-considered take on midlife debunks the mistaken popular opinion that midlife naturally sucks! He offers a deep, cerebral dive, exploring why midlife is now longer ( due to longer lifespans) and arguably more enjoyable despite its reputation.
For those who could use role models . . .
Life is in the Transitions: Mastering Change at Any Age by Bruce Feiler
After interviewing over 200 people for his Life Story Project, Feiler found that they had experienced, on average, four “lifequakes”—his term for major disruptions that last 5-10 years before a new equilibrium is found. Half of their lives were spent in adapting to these major life changes. “The linear life is dead,” he concludes. In other words, transitions are coming, so be prepared! Reading these inspirational stories of trial and tragedy turned into triumph is a good start.