The CEO Who Couldn't Afford Shoes

My father ran a chemical company from a private office suite with a kitchen, bathroom, balcony, and boardroom larger than my first house. He had made the cover of a business magazine. Yet he often told me he was broke.

In middle school I owned one pair of grubby sneakers, holes worn through the sides and stained green from mowing lawns. When I asked for a new pair, he said, "Go ask your mother for the money. She has all of mine in alimony." I was a boy. I believed him.

He was not lying, exactly. He believed it too.

He grew up poor in Altoona, PA, the son of an Irish flour salesman. After school he and his siblings scoured alleys and roadsides for discarded soda bottles, each one worth a nickel toward supper. He learned early what it was to have nothing, and he was afraid of it for the rest of his life.

He sprinted up the corporate ladder as if a bonfire licked at his heels. The man in the corner office was still, deep inside, a frightened boy looking for bottles to trade for a meal.

That is the thing about a wound like his. No amount of money closes it. He could have owned the building and still felt broke, because the brokenness was never in his accounts. It was in his chest. He was not cruel. He was terrified. It took me decades to learn the difference.

I swore I would never become him.

So I did the opposite. I took a vow of poverty and became a monk. I thought I had solved the problem my father could not. But I did not escape his fear. I only turned my back on it, and it followed me all the way into the monastery.

There I lived alongside a brother I will call Br. Pious. Unlike my father, he would not touch money at all because he believed it polluted the soul. No cash, no checks, no cards, for years. He thought this made him holy.

Instead, it made him insufferable. As the monastery's business manager, I handled the books, the bills, and the roof over his head. Br. Pious floated above all of it, his hands clean and his judgments pure. The less he touched money, the more righteous he grew, and the more I became, in his eyes, the worldly one who had lost his way.

He taught me something he never meant to teach. Refusing money for the wrong reasons does not shrink the ego. It feeds it. Br. Pious had not freed himself from money. He had only found a higher perch from which to look down on everyone who handled it. His poverty was not holiness. It was a money monster wearing a halo.

Only later did I see the truth. Br. Pious and my father were not opposites. They were the same man running in opposite directions, both asking money a question it could never answer: whether they were worth anything at all.

Fight. Flight. Freeze. These are our ancient survival responses, and money triggers them all. To our deepest animal brain, money means survival: food, shelter, status in the tribe.

My father fought. He swung at his fear with everything he earned. Br. Pious fled, racing so far into poverty that he mistook the running for holiness. I froze. I removed money from my life and mistook avoidance for freedom.

The real work is neither gripping harder nor finally letting go. It is to stop outrunning the fear that first taught us to run. My father never managed it. Br. Pious never managed it. For a long time, neither did I. They were good men who suffered deeply. And they handed that suffering, gift-wrapped, to the people who loved them. I know because I inherited it.

As Richard Rohr likes to remind us: "If we do not transform our pain, we will most assuredly transmit it, usually to the most vulnerable, our children."

But the reverse is true as well. What we heal, we redeem. The same pain that ran from my grandfather to my father walks into my office most weeks. I know it on sight. I carried it myself for decades. It stops with me, not because I make more money or want less, but because the shoes I wear no longer measure the worth of the feet inside them.

The information contained in this column is for educational purposes only and should not be construed as personalized investment, tax, or legal advice.