As young men in high school many decades ago, my best friend and I would often engage in discussions more of a philosophical nature than those focused on topics such as girls, drinking, and rock and roll. Which isn’t to say those topics held no interest for us; rather, if we talked about girls, for example, our perspective would be to consider the questions of relationship dynamics instead of perhaps the physical types we each found most appealing. At least most of the time. We were a curious pair, and almost anything would set us off on some conversational vector with the intent to arrive at the “why” of a particular subject. Curiosity, certainly a precursor to wisdom, is the province of youth… and all the more for those raised on a steady diet of Rod Serling monologues.

In my best friend’s basement—which is where we spent many afternoons and weekends in conversation—there was a painting on the wall: Christina’s World by Andrew Wyeth. Understand that it was a time pre-Internet, so researching information out of casual interest was an involved process of finding an expert to talk to or going to a library. We did the next best thing, which was to engage our imaginations and lay out plausibilities. Why was the woman sitting out on the grass like that? What was the significance of the cut inner circle of grass and the longer grass where she was? We spent a lot of time asking questions and positing answers, and somewhere in there we began to understand it was the process of scaffolding answers into an interpretation that was the important thing. What we couldn’t articulate then was that being able to interpret stacked knowledge was one of the first paths to wisdom. We began, in earnest, to examine circumstances around us and how they affected the thoughts and feelings we held inside. As Socrates said, “the unexamined life is not worth living.”

The fat man in the cave

So we started examining life. Imagine this: two teenage boys living in the suburban mid-Atlantic region of the Unites States with precious little actual life experience decide to examine life. In that context, what does it even mean to “examine life”? In the best tradition of Captain Kirk seeking out new life, we decided to define our strange new worlds by setting up fictional thought experiments and discuss our way through to understanding concepts, including right versus wrong, good versus evil. We named one such thought experiment “The Fat Man in the Cave,” and it went something like this:

You’re in a cave, with only one way in or out. A fat man (remember, we grew up in the pre-woke, pre-PC era) somehow gets his butt stuck in the cave entrance so that there is no way out. There is no hope of rescue for either you or the fat man before you suffocate. Your only option for survival is to kill the fat man to escape. Are you morally justified in killing the fat man to save yourself? In other words, is murder justified to save your life? To change the moral calculus, let’s suppose further that your family, spouse and children, are in the cave with you. Does that make killing the fat man an easier choice?

Imagine this: two teenage boys living in the suburban mid-Atlantic region of the Unites States with precious little actual life experience decide to examine life.

Many discussions flowed from that and other moral dilemma scenarios, and at one point we considered writing a book, which we never got around to. We did, however, read a number of authors, one of whom was Will Durant who said this in The Story of Philosophy:

“And last are the few whose delight is in meditation and understanding; who yearn not for goods, nor for victory, but for knowledge; who leave both market and battlefield to lose themselves in the quiet clarity of secluded thought; whose will is a light rather than a fire, whose haven is not power but truth: these are the men of wisdom, who stand aside unused by the world.”

We continued our experiments and discussions, seeking truth in our way, sometimes with interspersed ruminations of girls, drinking, and rock and roll. Looking back, it was during that time that I began to see the value of dialogue as a road along the way to wisdom—not the whole path, but a major segment of the journey. The cultivation of wisdom requires dialogue. That can be dialogue between self and others. Or it can be dialogue between present self and past self. And that requires a bit of time travel and self-awareness. As Aristotle observed, “Knowing yourself is the beginning of all wisdom.” Let’s consider what that time travel and self-awareness look like.

The cultivation of wisdom requires dialogue. That can be dialogue between self and others. Or it can be dialogue between present self and past self. And that requires a bit of time travel and self-awareness.

The accessibility of wisdom

At any given point in life, a person has thoughts and opinions that have been formed on basis of experience and information. The very act of living, interacting with people, consuming media, and participating in society provides additional experience and information during subsequent life points that (hopefully) contribute to growth and transformation. The elegance of wisdom is that a person does not need to know the source to reap the benefits. Nor does the particular source for a person need to be the original source of the wise epiphany or guidance. For example, is there much difference between Aristotle sharing with me his thoughts on the beginning of all wisdom and reading about it from the Internet… or a fortune cookie, for that matter? While the sources of wisdom may be obscured or lost in time, pearls of wisdom are able to multiply and spread through a great variety of means, far and wide.

From a Biblical perspective, the source of wisdom is God. Proverbs 2:1-6 reads:

My son, if you accept my words
and store up my commands within you,
turning your ear to wisdom
and applying your heart to understanding—
indeed, if you call out for insight
and cry aloud for understanding,
and if you look for it as for silver
and search for it as for hidden treasure,
then you will understand the fear of the Lord
and find the knowledge of God.
For the Lord gives wisdom;
from his mouth come knowledge and understanding.

The elegance of wisdom is that a person does not need to know the source to reap the benefits.

The words of God’s wisdom are not limited to the Bible (nor is the wisdom from other religious texts so constrained). The wisdom of religious texts thousands of years old have spilled liberally into modern civilization. While Uncle Ben may have told Peter Parker that “with great power comes great responsibility,” many will recognize the source to be scriptural: “To whom much is given, much will be required” (Luke 12:48).

Because of the way people share ideas that are important and meaningful to them, wisdom constantly travels around and across a plane of collective consciousness. The same messages fall on different sets of eyes and ears in the ways that are most accessible to different people, if they are open to receiving the messages. Christina’s World, for whatever insight it provided to two boys in a basement in a Maryland home in the 1970s, was in the movie 2001: A Space Odyssey as well as acted out in a scene of Forrest Gump; when Forrest’s friend and love Jenny returns home, she throws herself on the ground in a mirror image of the pose of the woman in the painting.

Wisdom is passed from generation to generation through the writers and artists and poets of the age, and even now as filmmakers, bloggers, social media influencers, and TikTok personalities. This is one way that the wisdom of the ages remains eternally in our consciousness. How else to comprehend Shakespeare’s admonition in the year 1600: “Neither a borrower, nor a lender be. For loan oft loses both itself and friend” showing up on an episode of Gilligan’s Island in the 1960s? It’s a simple matter to survey popular media today to see how much the truths of eternal wisdom have been infused into the fabric of society in grand tapestry of the world’s civilizations throughout time.

Among many other topics there is wise guidance all around us on the satisfaction of raising children, the humility in caring for those in need, the value of being a good friend, the importance of generosity, the healing qualities of forgiveness, the happiness in feeding your inner child, the joy of loving and being loved well, and the way to live and die having had a fulfilled life. Science Fiction author Robert Heinlein, himself often a conduit of eternal wisdom, gave his perspective on what it takes to be a fulfilled person:

“A human being should be able to change a diaper, plan an invasion, butcher a hog, conn a ship, design a building, write a sonnet, balance accounts, build a wall, set a bone, comfort the dying, take orders, give orders, cooperate, act alone, solve equations, analyze a new problem, pitch manure, program a computer, cook a tasty meal, fight efficiently, die gallantly. Specialization is for insects.”

The embedded wisdom here is not so much that accomplishing these tasks makes for a wise person, but it is more in the realization that attempting these things prepares a person to be open to the accessible wisdom that surrounds us, and that is available to us all until the very moment we die.

The wisdom of the death bed 

One of the slivers of wisdom I have learned is that there are things worse than death. Having such a perspective surely touches the way a person lives life; it provides comfort in the understanding that there can be great value in sacrificing your life for a cause or for other people. In his 1842 collection of narrative poems, Lays of Ancient Rome, Thomas Babington Macaulay writes in the first verse of “Horatius”*:

Then out spake brave Horatius,
The Captain of the Gate:
“To every man upon this earth
Death cometh soon or late.
And how can man die better
Than facing fearful odds,
For the ashes of his fathers,
And the temples of his Gods.

How we die is as important as how we live, and what matters to us when we come to that moment of passing is what should have mattered during all the years that came before. If you want to know what’s important in life, look at what a person talks about on their death bed. When my father passed away 20 years ago, his family (my mother and two sisters) were there bedside him as he recollected the high points of his life to the doctor and nurses in attendance. Although his life story is filled with accomplishment and material success, he would only talk about us, his wife and his children, and that all the joy and happiness he experienced with us over the years was still his joy and happiness even as he lay dying. Perhaps for me, this is the one piece of wisdom I hold closest to my heart: your greatest treasure in life should be the people that you love and not the things that you have accomplished.

How we die is as important as how we live, and what matters to us when we come to that moment of passing is what should have mattered during all the years that came before.

The irony of wisdom

Wisdom, sadly, is not a key to eternal happiness or a universal talisman against the heart-rending agonies of life. The irony of Wisdom is that not only does it not save a person from suffering, it transforms the suffering into something almost impossible to bear. But it gives meaning and affords understanding to those wounds that otherwise would have mysteriously appeared leaving the person simply with the plaintive question “why?” As Alexandre Dumas said, ”There is neither happiness nor misery in the world; there is only the comparison of one state with another, nothing more. He who has felt the deepest grief is best able to experience supreme happiness. We must have felt what it is to die, Morrel, that we may appreciate the enjoyments of life.” That’s a terrifying balance if you think about it, but it’s one that I welcome as part of my journey. And who is to say where it will end for any of us?

One way to look at it is through the words of Rainer Maria Rilke in the poem “Go to the Limits of Your Longing”:

God speaks to each of us as he makes us,
then walks with us silently out of the night.
These are the words we dimly hear:
You, sent out beyond your recall,
go to the limits of your longing.
Embody me.
Flare up like a flame
and make big shadows I can move in.
Let everything happen to you: beauty and terror.
Just keep going. No feeling is final.
Don’t let yourself lose me.
Nearby is the country they call life.
You will know it by its seriousness.
Give me your hand.

As we seek wisdom, it is important for us to keep going, because it is true that no feeling is final, even the terror that presses down on your heart. Especially the terror. The optimist in me looks for happy endings, and in that, I resolve Rilke’s poem through the lens of Sophocles (which, interestingly, I first heard from Richard Nixon as he was interviewed by David Frost):

“One must wait until the evening to see how splendid the day has been.”


*A few lines from the first verse of the poem “Horatius” were recited by Tom Cruise in the movie Oblivion. It’s worth mentioning that the painting Christina’s World was also in the movie.