On Defeating “It Might Have Been”

There’s no such thing as a bereavement-free life. Generally defined as “a state of loss that occasions a reaction of grief,” bereavement inevitably breaks into every human story, because we all experience significant loss: loved ones die, relationships end, health deteriorates, decades-long jobs are suddenly outsourced, children grow up and move cross country with grandchildren.

Losses like that can’t be blocked this side of paradise. But there’s another kind of widespread bereavement that often is preventable. Poet John Greenleaf Whittier once wrote: “For all sad words of tongue or pen/The saddest are these: it might have been.” The trips never taken and wonders never discovered; the talents never refined and new hobbies never learned; the “I love you’s” left unsaid and “I’m sorry’s” never spoken; the books never read and business ventures never tried: these “could have” and “should have” moments can cause chronic grief too. Though by definition never actualized, they are in a sense a kind of death too. The good news is that the right educational foundation can help liberate children from the “might have been” moments that will otherwise haunt their adulthood.

  1. Passions never pursued because “it’s too late.” Many people come to view time as a barrier instead of a gift, as if learning not accomplished by a certain year or life stage loses its value. That perspective tends to stem from a misguided understanding of the purpose of study: if it can’t be used to further a career, it’s relatively meaningless. But a good school impresses upon children that learning is meant to be lifelong. It begins in the womb and ideally continues right up until our deathbeds. To be sure, formal education is a particularly intense season of study, but it is only a season, and not necessarily even the richest. The right education helps students understand the immeasurable worth in learning how to garden in their 30s; in re-taking calculus just to get a better handle on it in their 50s; in picking up a new sport in their 70s; in studying a new language in their 90s. 

  2. Art never created because of perfectionism. There’s an age-old caution not to let the perfect become the enemy of the good. It’s reasonable to define “good” in that sentence to mean something like “imperfect, but good enough,” but in fact it’s more accurate to understand it as the Good. In other words, perfectionism - the fear of not being or appearing perfect - is anathema to goodness itself. It holds people back from living into their full potential, often by stifling creative impulses. A good school, therefore, teaches children from the beginning that flawlessness is an unworthy goal. It destigmatizes error and encourages students to fail spectacularly, confident that mistakes are of no consequence except as reliable stepping stones to greatness.

  3. Ideas never articulated because they’re outside the societal box. We live in a judgmental age, and many adults fear the hits their reputations and relationships may take if they seem to color too far outside the lines. Independent thinking is increasingly discouraged and in many communities the circle of acceptability is tightening. A good school fortifies students against the fear of shunning by enveloping them in the knowledge that they were each endowed with a unique and unrepeatable perspective that is not weird, but wonderful. It broadens their horizons through time and space such that contemporary opinion loses its omnipotence. And it gives them confidence that they belong in the great conversation about the best way forward for the human race.

  4. Risks never taken because “the market is already saturated.” Many people restrain their entrepreneurial spirit because they doubt their visionary capabilities. They can’t see themselves as pioneers, captains of industry, or community leaders because they believe “the experts” have already cornered the market. But a good school teaches students that, like truth itself, the opportunity for discovery is infinite: whatever the subject matter, there’s always another depth to plumb, and the exploration belongs to everyone of good will. It equips them with the tools to blaze trails, teaching them how to appraise reality from every angle and confront new challenges with a formidable blend of knowledge and imagination.

  5. Relationships not maintained because of “more important things to do.” It’s easy for adults to become trapped on the corporate ladder as we climb for more money, more success, and even more ability to do good with our time, talents, and treasure. Certainly not bad goals in and of themselves, their luster can nevertheless become blinding and cause us to lose sight of the people right in front of us. A good school helps students properly prioritize people over projects and teaches them that without love, achievement is meaningless and advancement worthless.

No one entirely escapes those “saddest words” in this life; even those who grew up on the most solid foundation will occasionally have to navigate the bereavement of regret. But the right school can unshackle children from most of the fears, doubts, and limits that tend to hold us back later in life. In short, it can prepare them for lives in which the deathly sorrow of “it might have been” is almost entirely overthrown by the vibrant joy of “it was and is.”

-Johanna M Webber

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The Year in Pictures, 2022-23