By Herbert Hadad

That bitterly cold winter, I lived in a state of dread. I tensed when the phone rang and avoided fetching the mail. I was ashamed to tell my family the oil bill was past due.

The children were small, and Evelyn was a stay-at-home mom. I was working three freelance jobs, but, still, there wasn’t enough money.

I stayed awake imagining the oil company calling to say they couldn’t make another delivery until I made good on the 1,000 gallons they’d already provided. To save fuel, I convinced my family to gather in the evenings by the living room’s large fireplace, though its warmth was considerably more decorative than real.

By some miracle, the oil company temporarily overlooked the money owed. By the time early spring—and the bill—arrived, I’d earned enough to get back on top of all my obligations.

Even in my relief, I couldn’t help wondering: Why hadn’t I built a nest egg like everyone else? Accumulating wealth seemed like a fine thing, the responsible thing, to do. So how come a nice guy like me never got rich?

I thought of a woman I knew a long time ago in Boston, a descendant of one of New England’s ruling families. She liked me. She liked me a lot. The first time she picked me up was the first time I’d been in a car with polished wood paneling. “Have you ever driven a Mercedes?” she asked with a smile. “Would you like to?”

We drove to Cape Cod, where a motor launch took us over to an island. We met her cousins in a huge kitchen in a huge house. The men hunted for pheasant and fished for striped bass while the women prepared soups and vegetables. My friend’s family owned the island.

Back in Boston, she made elaborate dinners, read Shakespeare’s sonnets out loud, and talked about our future together. She suggested I could stop working and stay home with her and write.

“What if I turned mean?” I asked, trying to picture myself as a kept man. “It would be okay, because you’re talented,” she said.

I don’t think we had ever kissed. We didn’t have that kind of relationship. Yet she was inviting me into a life of unimagined luxury. One night, I saw a means for escape: I brought a date to a party we had both been invited to. My wealthy suitor got the picture. I never had to tell her that I did not return her ardor, that we had no serious future together.

A short time later, wealth appeared to beckon me again, without any labor or encouragement on my part. Two of my mother’s friends went down to Miami Beach for a vacation. When they got back to Boston, they came to our apartment breathless, almost falling over each other to tell us what had happened.

They had gone into a linen shop on Collins Avenue, a posh stretch in Miami Beach, and found some tablecloths and napkins they liked. But they wanted to haggle over price. The proprietor engaged with them for a while, then decided they were too stingy.

“I’m not going to sell to you,” he said abruptly. “I’m a sick man. I’m getting old. When I go, everything I own is going to my nephews and a niece in Boston.”

Boston? They pressed him for details. What they heard made them shout.

The shop owner was my Uncle Charlie, my father’s oldest brother. He owned the store along with some Florida property and a portfolio he had begun well before the Great Depression.

“Your Herbie and Alvin and Sybil are rich!” one of the women said to my mother, who got excited, too.

I was a young adult without strings. Common sense should have dictated that I visit my uncle to ensure he was all right or ensure my standing if he were not. He had no children, and his wife had already passed away. I remembered fondly his many visits to our home, always with gifts. He had a confident, jolly manner, and my father was always glad to see him. But, instead of flying down to Florida, I did nothing except pray that my uncle was well.

A year later, my dad phoned me. He was crying. “Your Uncle Charlie has died,” he said. My dad never cried, so I started crying, too. Dad made the trip to Florida.

When he returned, he held out his hands, palms up. Unscrupulous creditors and lawyers had pounced on Uncle Charlie’s estate like hungry lions on a wounded animal. “They cleaned him out,” my father said. “They left nothing. They even said he still owed them.”

It’s not that I was completely devoid of entrepreneurial tendencies. I used to own a rustic weekend home outside Woodstock, New York. I enjoyed spending time there despite one shortcoming—the area had no Chinese restaurant. I convinced the owner of a Greenwich Village restaurant I frequented to come up and scout locations, arranging for a real estate dealer to show us around.

“People flock to this town by the thousands on weekends,” I told my restaurateur friend. “You arrange for the cooking and the servers. I’ll be the host and greeter.” I liked the prospect of welcoming diners to a good meal. I didn’t tell my friend I also dreamed of unending helpings of what was then my favorite food, sweet and sour chicken with pork fried rice.

Just when I could envision an end to my workaday, salaried life, the restaurant owner gave me the news. “I talked to my partners,” he said. “Woodstock has no strip mall, and they’re afraid to open without parking. So we’ll have to say sorry, we can’t.”

Today, I lead a simple, contented life in Pocantico Hills, New York, about twenty-five miles north of New York City. Curiously, though, it is a town filled with famous, monumental wealth. My wife, Evelyn, and I have had dinner at the home of David Rockefeller, a charming and relaxed host. The walls of his home are adorned with some of the most fabulous impressionist paintings of the nineteenth and twentieth centuries.

Ten miles up the road, in Bedford, my wife manages the estate of George Soros, the billionaire hedge-fund manager and philanthropist. On occasion, his French chef has cooked us incredible meals, served with fine French wines. The next night, the menu at our house might be a slice of pizza, a small salad, and a glass of Yellow Tail.

Writer and journalist Benjamin Cheever, the son of novelist John Cheever, is another neighbor. Though the elder Cheever was showered with international literary acclaim, he spent a good part of his life scraping by financially. I told Ben I was exploring how the pursuit of wealth figured in my life.

“Money has never been anywhere near the top of your list,” he e-mailed me in response. (How does he know? Is it so obvious?) “It’s not what you think about. It’s not what you work for. You’re interested in your children and your heritage. You like it when conflict dissolves into understanding. You like a spectacle, and you like a laugh.”

He went on: “I’ve been shamefully poor and also quite comfortable. When I had very little money, I was free to imagine that cash solved most problems. The stuff sure does look fabulous from a distance. I know now how little it’s actually worth.

“Now fame looks great,” Ben wrote. “But I bet if I got that, I’d find it equally disappointing.”

I needed heart surgery about a year ago. After I got home from the hospital, I began to buy and sell Persian rugs. I was looking for a way to make money. Among other enterprises, my father sold rugs, too, so it felt like an activity that was in my blood.

“This is going to be the wealth I leave the children,” I told Evelyn.

My sensitive wife understood it differently. “It’s for your soul,” she said. “It’s helping your recovery.”

I went to estate and tag sales, browsed in antiques shops, scoured the Internet, visited a mosque. I have about a hundred rugs in the house and have sold fifteen or twenty more. Sometimes I’m sorry to see them go.

And so, it seems, at every phase of my life I’ve exhibited a disregard for wealth. It was never really important enough to pursue.

What about the specter of the brutal winter and the unpaid oil bill? I realize there, too, my dread didn’t spring from an empty checkbook but from the fear of losing the love and respect of those I care for the most.

Every time the choice has been love or money, I’ve put my money on love.

Herbert Hadad, a Northeastern graduate and award-winning writer, says he’s willing to entertain requests for a loan, but make it a small one.