Last month, my 11-year-old son completed his first year at the Manhattan Country School without cataclysmic incident. My wife and I, both being dutiful Hennessy-sipping liberal elitists, were attracted to the school’s diversity of race and income, and even more attracted to the sliding scale for tuition, for reasons both societally broad and personally austere.

The school was the sort I thought I would have wanted as a kid — small classes, a great deal of independence and myriad activities to stimulate the mind.

But, in truth, from the first day I dropped the boy off, I was dogged by dark ancestral fears. School is the site of my most middling triumphs and my most spectacular failures. At the height of my powers I achieved the remarkable feat of being summarily tossed from Baltimore City’s best magnet school. Twice. When I departed the system of formal education my only possession was a fat mental dossier filled with report cards running red, and progress reports appended with comments like “conduct needs work,” “has trouble staying on task” and the dreaded “is not working up to potential.”

Worse, this penchant for scholastic underachievement was not merely my own. The male members of my family, from my father to most of my brothers, had specialized in the manufacture of frustrated educators up and down the Atlantic Seaboard. The fact that six of my father’s seven kids secured their college degrees has made this history the material of jokes at family get-togethers. But I, the degree-less seventh, have never laughed too loud.

I have often been told that I should be proud of having overcome my grade-school bungling, for having done it my way. “Remember,” these people say to me. “Einstein wasn’t good at school either.” The people doing the reminding were all A students. The fact is that anyone who spent his earliest years as a loser knows that failure leaves an indelible mark. A morbidly obese man can will himself svelte, but always he will be somehow escorted by his old portly self.

I can tell you everything that was wrong with my education — how cold pedagogy reduced the poetry of Macbeth to a wan hunt for hamartia, how the beautiful French language broke under rote vocabulary. But more than that, I can tell you what happens when education is decoupled from curiosity, and becomes little more than an insurance policy.

I was a black boy at the height of the crack era, which meant that my instructors pitched education as the border between those who would prosper in America, and those who would be fed to the great hydra of prison, teenage pregnancy and murder. That impulse still reigns today, and compelled by a disturbing range of statistics, it is utterly understandable. But for me it meant seeing learning not as an act of work and romance, but as a kind of hustle, a series of trials in the long effort to get over.

I did not get over. I failed repeatedly, until somewhere around 11, somewhere about my son’s age, I internalized it all. Thus prophecy came to fulfill itself, until years later, as a college dropout, I would lie alone asking myself, “What is wrong with me?” I know better now, but once you’ve internalized your failures, the bitterness remains at the back of the mouth.

By some stroke of luck and by a greater stroke of privilege, my son enjoys a school that is the opposite of what I knew school to be. His teachers have seen him as something more than a potential statistic, as something besides another brown face in a demographic overrepresented in all the wrong columns. For him education has been not just the shield, but the sword.

This is progress, but when experienced by a parent, progress begs to be overthought. The fact is that, in my time and in this time, education really is an insurance policy. It really is often the line between civilian life and jail. My failures at school left me, as well as my brothers, who endured their own struggles, at times unclear as to which tribe I belonged to. I was saved by the relentless energy of my mother and father, and the greatest education I received was in seeing those who lacked that advantage ultimately not make it.

“There before the grace of hard parents go I” was the lesson of my life. The lesson was unintentional and ironic. I acquired it in the midst of failure in the very environs that I now deem unfit. And so you must forgive my overthinking. I am watching my child grow in a new world of comparable bounty and privilege and I can’t help but wonder, and worry, at what unintentional lessons I am now imparting.