That night, I took my 12-year-old son, Will, to a Rangers game. It was near the end of the season, and Madison Square Garden was two-thirds empty. The seats we had ended up with were the two worst in the house—the last row in the last tier. Will looked miserable. I couldn’t stand the idea of having both of us be miserable, and the idea of feeling pinched and poor was intolerable on a day when I had just lost my job. We descended the escalators to the box office and bought front-row seats behind the Rangers’ bench.

As I watched the players flying up and down the rink and downed my third Dewar’s in a plastic cup, queasy about what the $300 charge for our two tickets would do to my next month’s Visa bill, I tried to get my head around the fact that I had been in New York for more than twenty years. What a bumpy ride: Were all lives like this? Was it a condition of existence that it never reached a plateau of even momentary equilibrium? I had come here at the age of 28, the provincial staking out his literary fortune. I had been intoxicated by the city, a kingdom of limitless aspiration, of vast and uncharted possibility.

Rangers stomped in and out of the box, throwing open the low door and charging out on the ice. I was always comparing my life with the lives of others, and found myself thinking of Isaac Rosenfeld, a classmate of Saul Bellow’s at Tuley High School in the thirties. Rosenfeld, like his best friend Bellow, was a book-besotted Chicago boy with limitless ambition; Tuley classmates thought Rosenfeld was the one who would go the distance. He and Bellow attended the University of Chicago together and were in lockstep until Rosenfeld beat him to New York, the city that, then as now, represented the apotheosis of all cultural ambition. While Bellow was still brooding on park benches in Chicago, Rosenfeld was rapidly making a name for himself as a critic. But he ran into heavy mental weather, became a Reichian, left his wife, suffered crippling writer’s block, and came to a poignant end. “He died in a seedy, furnished room on Walton Street, alone,” wrote Bellow in an obituary for his friend, “a bitter death to his children, his wife, his lovers, his father.”

This story fascinated me. What would have happened if Rosenfeld had lived? Would the furnished room on Walton Street have come to be seen as the place where he’d weathered a crisis? That was a tough time when I was living on Walton Street; I thought I’d never get through it. Or would it have been the beginning of the end, the moment when his life took a turn from which he would never recover? Who could say? He brought to mind Housman’s poem “To an Athlete Dying Young”:

Smart lad, to slip betimes away
From fields where glory does not stay
And early though the laurel grows
It withers quicker than the rose.

Why smart? Because he had escaped before the inevitable erosion of his early promise. He hadn’t had time to fail.

One night when they were maybe 9 and 13, I took my children to see Mr. Holland’s Opus. This is the movie, if you recall, where Richard Dreyfuss plays a high-school music teacher with a deaf child and major frustration over the fact that he didn’t end up a famous composer and had to settle for conducting an orchestra of pimply kids. I wept through the whole movie. Dreyfuss having a fight with his impaired son and then tearfully making up; Dreyfuss yelling at the orchestra’s hapless tympanist for losing the beat, then praising him tenderly when he gets it right; Dreyfuss being forced out of his job by a heartless principal.

The paper napkin I’d gotten with my popcorn was twisted and soggy. Mr. Holland hadn’t achieved all he might have wished to in life. He had, in his own eyes, failed. But he had also redeemed himself by giving something to the world. It was possible to survive the pain of falling short—and even to make something of it. At the end, when the stooped and white-haired music teacher, lured to the school auditorium on some pretext, walks in to find his former orchestra, now middle-aged themselves, on stage, instruments in hand, and the conductor brings down his baton with a swift and decisive chop and they begin to play the symphony on which Mr. Holland has been laboring for most of his life, it was too much. I broke down, my shuddering sobs causing people in the row in front of us to turn around and stare while my two mortified children gazed down at the grimy floor in mute alarm.

What’s with Dad? they must have thought. How could they begin to grasp the power of my identification with this man? In their eyes, I was Dad, a man who went to work, came home with his bulging briefcase, and seemed to make his way in the world. He talked on the phone in a loud, authoritative voice. He was no hollow-cheeked loser, disheveled, wan, his tie askew. He provided for them, sat upright at the dinner table, helped them with homework. He had a closet full of suits. How could they intuit his conviction that he was a failure? There was no way to explain it—either to them or to himself. It existed within him, a condition that had no cause, no reason. It made no sense, yet he believed it to be true. Don’t you see, children? Your dad thinks he’s Mr. Holland.

On a school night in the winter of 1965, I’m sitting in the basement of my parents’ house in Evanston, Illinois, transfixed by the black-and-white film on TV. Beside me on the couch are my father and mother. On the screen is Fredric March in the role of Willy Loman. The play is winding down as we sit there numb in a row, tears rolling down our cheeks. The last two hours have been wrenching, ghastly, like watching a car crash. At moments—the scene where Willy gets fired; the scene where Biff and Happy abandon Willy in the restaurant and go off with a pair of whores—I’ve been flooded with a desolation far beyond anything I could have imagined it was possible for a 16-year-old boy to feel. The house is still, and a funereal silence settles over the room as Linda, Willy’s wife, lays a wreath on his grave. I hear a car go by outside.

Then Charley, Willy’s friend, is speaking:

“Nobody dast blame this man. You don’t understand: Willy was a salesman. And for a salesman, there is no rock bottom to the life. He don’t put a bolt to a nut, he don’t tell you the law or give you medicine. He’s a man way out there in the blue, riding on a smile and a shoeshine. And when they start not smiling back—that’s an earthquake. And then you get yourself a couple of spots on your hat, and you’re finished. Nobody dast blame this man. A salesman is got to dream, boy. It comes with the territory.”

What is my father thinking, sitting there with his hands on his knees? Is he thinking of his father, a timid man who came over on the boat from Russia with an engineering degree and mastery of half a dozen languages, only to end up running a corner drugstore on the Northwest Side of Chicago? Or is he thinking of himself, not as timid as his father, but somehow not possessed of quite enough of that go-getter quality, prevented by his nature and his limitations from following his dream? What he had really wanted to be was a professional musician, to play the oboe in the Chicago Symphony Orchestra. But it was the Depression: He needed to make a living, and so he became a doctor, hardly a humiliating profession. After all, he didn’t go into advertising (which isn’t so humiliating either). His tragedy—or is that too strong a word?—was that he failed to achieve what he’d hoped to achieve. He wasn’t a defeated man; he was a thwarted man—one of the most common human conditions.