“I could have been a contender.”
These are the words of Terry Malloy, the boxer turned longshoreman in On the Waterfront, and they mean more once you know how he gets there. He had real promise, before he let his brother talk him into throwing a fight so the men running his union could collect on a bet. Years later, in the back of a cab, that same brother is sent to keep him in line, and the whole debt comes due at once: “I coulda had class. I coulda been a contender. I coulda been somebody, instead of a bum, which is what I am.” It isn’t about boxing. It’s a man naming, out loud, the exact moment his life turned away from what it might have been.
That’s why it lands. It names the gap between who we thought we’d become and who we actually are, the gap that middle age stops letting you pretend is theoretical. The road not taken closes. Not with drama. Just with time.
Usually we do one of two things in response: mourn it, or pretend it isn’t there. I want to try something different.
My family had a textile business, two generations deep—the unglamorous kind that a life gets built around, until cheaper labor and faster shipping made forty-five years of our name stop mattering. Dad tried to reinvent himself: retail, then real estate. I pushed him to keep trying because that’s what a son does: You believe your father’s capacity is inexhaustible because you need it to be. Then his illness took hold, and I understood, later than I should have, that the well he was reaching into had gone dry. I reinvented myself too, into finance and real estate, the sensible things, unfulfilling not because I did them badly but because they weren’t mine. So I did something my mother could not have imagined and would not have chosen: I left it all behind to become a rabbi. (My mom always hoped I’d become a doctor and go to Harvard.) But I’d be lying if I said the question closed. It just changed shape as I got older.
A lot of us have a romantic notion, seductive because it flatters us, that somewhere inside us was a fuller, truer version of our life—and that everything we did diminished it. That notion requires imagining a version of yourself untouched by a father’s illness, unaffected by untaken or unsuccessful risks, and unshaped by every constraint of the life you actually had.
That person never existed. No road not taken, just a fiction. Mourning a fiction is a strange way to spend the only life you get.
Mine is not a story about a promise unkept. It is a story about what grows in the actual soil I was given, the only soil there ever was.
There is a Hasidic story about Reb Zusya of Hanipol, who came to his students one morning, trembling after dreaming of his own death and the judgment awaiting him. They expected him to say he feared being asked why he hadn’t been more like Moses, why he hadn’t parted a sea. That wasn’t what frightened him. The question was: Why weren’t you Zusya? Not why didn’t you become the figure some other soul was built to become. Why didn’t you become, completely, the one thing only you could ever have been?
I did not expect to find the same teaching from the American businessman Mark Cuban, but when he was once asked about reincarnation, he said that if he came back, he’d like to come back as himself. Not younger, not richer, not luckier. Himself. A life that had been entirely his, imperfections included, was the thing worth having again.
But I don’t want to let myself off the hook that easily. There’s a second question beneath the first, and it might be the harder one.
Anyone who has raised children knows something philosophy took centuries to catch up to: Personality doesn’t start as a blank canvas. It shows up. Before language and before nurture has time to work, a child is already themselves. Torah knew this before we had a word for temperament. Rebecca feels her twins struggling inside her, vayitrotzetzu habanim b’kirbah, and is told, before either has drawn breath, that she carries two already divided nations. Jacob and Esau don’t become different men through different parenting. They arrive different.
If that’s true, the question isn’t only whether I became what I could have been. It’s whether I did right by the person already there, in the people I was given to raise, teach, and sit with. Did I recognize what was already present, or spend those years trying to instill in them the shape I’d privately hoped for for myself?
I pushed my father to become something his illness had already made impossible, because I loved him and couldn’t accept the alternative. I have had to unlearn that same instinct with the people I love now, when I keep choosing to will potential into being rather than stewarding it toward where it already wants to grow.
So I leave the question where I found it. Not whether I could have been a contender. Not even Zusya’s question, exactly, because that one was his to ask. Mine is smaller: What did I do with what was mine: the business that collapsed, the father whose strength ran out, and the people I was given to raise, teach, and sit with, already formed and asking only to be seen? Am I what I should be for them?