My second son, Robert, started high school recently at Cranbrook-Kingswood, a college preparatory school that opened in 1922 whose 319-acre campus is a national historic landmark. We live a mile from school, and it has long been my destination for biking, running, and meditative nature walks with my children. Its architecture and physical beauty are almost surreal, leading me to wonder whether mere mortals inhabit the place.
When I was twelve I asked my parents if I could go there. I recall learning about it from camp friends and somehow just knowing it was for me, kind of the way Robert felt after he spent a day shadowing another student there in eighth grade. The story of where I ended up in middle and high school, and why, is too annoying to recount, but suffice it to say that I never got over my love affair with Cranbrook, and reflect to this day with regret on what might have been. When I drop Rob off on campus or hear about what he learned that day, the joy that I feel for him, because he understands how magical a place it is, is tinged ever so slightly with sadness.
It’s an obvious cliché that everyone has regrets. Not always from lack of gratitude or unhappiness, but perhaps just irresistible wonder at all of the possibilities that might have been. Where would we be today? Doing what? With whom? What would it have felt like? What intriguing thoughts, which, according to some, should not themselves be regretted. Henry David Thoreau advised: “Make the most of your regrets; never smother your sorrow, but tend and cherish it till it comes to have a separate and integral interest. To regret deeply is to live afresh.”
Perhaps not if you’re Woody Allen, though, whom most of us probably channel more so than wise Thoreau in feeling that, “My one regret in life is that I am not someone else.” Much of what we do involves a struggle to be other than who we are, and it comes to a head during midlife and its proverbial “crisis.” I recently read this truly weird little book on the subject called The Middle Passage which was sent to me by a thoughtful friend.
The author, a Jungian analyst named James Hollis, frames midlife as a transition from living according to (what we perceive as) others’ expectations to living in harmony with our own. During childhood we conform to our interpretation of our parents’ behaviors and attitudes, and starting in adolescence we mold ourselves according to our perception of our peers’ and society’s demands. The rift between our true nature and reactive one becomes increasingly untenable as we reach midlife and, as Hollis puts it, our “capacity for self-deception is exhausted.” First, most of our youthful dreams and delusions crash down to earth: “To flounder amid ordinariness is the sour leaven of midlife.” Men go out and buy the red race car and the trophy wife. Women suddenly feel what psychologist Marcia Reynolds calls “the burden of greatness.” They were always told of their endless potential, and now they look around and wonder why it wasn’t achieved and what they can do to fix that.
Next, our desires amp up just as our body starts refusing to cooperate. As Hollis notes, this was expressed most poetically by W.B. Yeats in Sailing to Byzantium, which reflects on the harsh conflict we endure in midlife between our still-nascent dreams and our failing bodies:
That phrase, “fastened to a dying animal,” haunts me as the small pains and indignities of aging slowly creep into my awareness. Hollis fortunately finds a way to put all of this in a positive light, observing that increasing awareness of “the fact that one is mortal, that time is limited, and that no one will deliver us from the burden of responsibility for our lives, serves as a powerful incentive to be more fully oneself.” Midlife offers us each the opportunity to come out in the fullest sense of the term. It requires courage and much effort, but the rewards are rich.
I’ve been searching the annals of western philosophy for insights on the nature of the middle passage and how to reflect clearly upon it. So far I’ve found interesting thinking by the ancient Stoics but not much else. Soon I hope to share their insights on the topic, as I can hardly suppose I am alone in feeling its weight.
What does the Dalai Lama’s wisdom have in common with blogging? I ran into this quote from him several times recently, and it was too good to let go: “If you want others to be happy, practice compassion. If you want to be happy, practice compassion.” One thing it called to mind—aside from the gut sense that the DL had identified the meaning of life in seventeen words—was a remark that my favorite nutty, always brilliant blogger, 
So, my friend, Jim Bellinson, called me and asked a favor. He was headed to Africa with his own and two other families and wanted a daily philosophy topic for group discussion. He felt the kids would learn something and enjoy it—and the adults, too. I loved the idea, and I’m sharing this list of issues today in the hopes that it will spark some thoughtful conversation—whether you’re traveling for the holidays with your kids or just sitting around with them on a winter’s night.
