BUSINESSMAN by Jim Windolf

BUSINESSMAN by Jim Windolf

My father told me, when I was fourteen, that business was a language anyone could learn. I never got fluent. So there I stood, a thirty-six-year-old man with not much in the bank, at the side of a hole in the ground as they lowered the coffin that contained his body.

He had run a small empire in our New Jersey town. His main business was an insurance agency. There was also a travel bureau, a movie theater, and a restaurant. Of all his businesses, I probably liked the travel bureau best.

He took me there now and then on summer mornings when I was six or seven. The place had a smell of paper and perfume. I would sit on a swivel chair at an unoccupied desk, tapping at a computer keyboard, watching the green letters jump across the dark screen, while my dad spent time in an interior office going over things with the mustached man who was the travel bureau’s president. A pair of sisters who worked there would put their faces close to mine. They also gave me candy from their desks, sour balls and Mary Janes, and they teased me about my curly hair, saying it was wasted on a boy.

After college, with the idea of eventually moving up in my father’s organization, I went to work in the warehouse that supplied his various businesses. But it turned out I was only ever good—unusually good, that is—at two things, sports and sex, and I have ended up making my small living at both.

I fell into sex work nearly ten years ago, during a cruise-ship vacation I took with my parents, my sister, and our baby brother, who had just finished high school.

It was the first time we had gone on an extended family trip as adults. I couldn’t shake the feeling we were trying to re-create our vacations of years earlier, although we must have been aware we had lost the old everyday mix of conflict and ease that animates families when they are young. So instead of playing hide-and-seek in a churchyard near a shingled seaside rental, or finding ourselves in the silence of nature as night fell and the blood thrummed in our veins, my siblings and I would put ourselves through three-hour dinners, sometimes at the captain’s table—meals that started with cocktails and crystal dishes filled with puckered olives and radish slices flavored with olive oil and flaked salt.

The ship was pushing through the northern Atlantic at one in the morning when I looked up from a craps table and into the eyes of a woman who must have been twenty or twenty-five years older than me. I was the last member of my family in the little casino, and she might have assumed I was alone in the world. I wasn’t surprised when I ended up in her cabin for what remained of the night, but it did catch me off guard, in the morning, when she lifted her head and aimed a glance at a stack of bills on the black coffee table. I took the cash as if I had done it before, and by the end of the next cruise, which I had booked solo, I found I had made more than I had spent.

After three years at sea, I knew the major ports and hated my morning reflection. When I heard about a job opening at my old school, I decided to apply.


My father, still firm, with a senator’s handsomeness, died of a mysterious illness in his seventy-third year, a week after undergoing hip surgery in October 2019. Six months later, while under quarantine aboard a small ship in the Mediterranean, I couldn’t help wondering if he had contracted an early case of Covid-19.

The memorial service took place on a crisp morning, with sharply outlined clouds parading across a marine blue sky. I didn’t see anyone crying at the grave site. He had been too large a presence for that. We felt like a mountain had been blown off the earth. The next day I went back to the high school where I had been employed six years — the same school where I had set records, since broken, as a member of the cross-country, basketball, and baseball teams.

The 7:45 a.m. faculty meeting was the usual mix of administrative talk and rank gossip about troublesome students and their parents. I got nods of concern from colleagues between the P.E. classes I ran. At 3:15 I drove the rowdy cross-country boys in an Econoline van to South Mountain Reservation for another practice. I felt like an orphan, now that I had no father, but I also felt the same.

The routine that had kept me in line since I had left the ships remained in force until the Monday morning when I got an email from the principal inviting me to see her in her office. We had not spoken in the weeks since the death of my father, and the first thing she said was, “I was so sorry to hear about your loss.”

I knew something else was up when her grave expression didn’t fade as we arranged ourselves in the deep leather chairs. She took a large smartphone from a blazer pocket and held it to my face. I saw screen shots of certain text messages between me and the mother of a boy on the cross-country team.

“I think this is a private thing,” I said.

“I’m not so sure about that. We received a batch of similar texts and emails going back roughly to the start of your employment.”

I wondered how my correspondence with the moms had ended up in a single file. I tried to figure out who would have sent it to my boss, and why.

“How would you like to do this?” the principal said.

“Do what?”

“I can accept your resignation. Or the school can terminate your contract.”


When I was a teenager, sort of as a joke, I started calling my mother “Ma.” She said she hated it and gave me light punches to the shoulder whenever I used that word. I stuck with it, though, and I think it helped set our relationship apart from the ones she had with my siblings. And so when, more than a month after Dad’s death, I told her I had lost my job and was going away, she insisted on seeing me off. I’m not so sure she would have done the same for my brother or my sister.

“I wonder if I’ll ever see you again,” she said.

“Don’t be dramatic, Ma.”

At sixty-seven, she was still a good driver, able to zip her Audi from lane to lane of traffic-clotted Route 3 and sneak between the rival buses, trucks, and cars on the helix that led to the mouths of the Lincoln Tunnel. Just as I had done as a child on drives to Manhattan, I kept an eye out, as we pushed through the rightmost of the three Lincoln Tunnel tubes, for the painted tiles marking the border between New Jersey and New York.

“I don’t understand how a person loses their job and then goes on a cruise. What will you do for money?”

“I’ll be all right.”

“I don’t understand where you got this wanderlust.”

“Maybe you and Dad shouldn’t have taken me on the cruise that time. Or maybe it was the travel bureau. I always liked it there.”

“I would think you’d want to do something a little more useful.”

“I’ll be useful.”

She found a metered spot on West Forty-Second Street between Tenth and Eleventh avenues, and we walked under a gray sky toward the Hudson. I used my left hand to steer the boxy rolling suitcase that trailed me and my right to carry the soft hanging bag that contained the three suits I had bought online, not to mention the tux I’d worn on formal nights during my earlier years at sea.

“Got your passport?”

“Got it.”

“Can I wave to you from shore? Like people did in the old days?”

“You might have to wait for me to go through the safety thing, with everybody sitting in an auditorium, wearing life preservers.”

“I’d forgotten about that.”

Near the spot where the U.S.S. Intrepid was docked, we waited for the white walking man to show up on the sign before crossing the West Side Highway.

We turned right. Now coming into our view, partly obscured by a concrete structure, was the ocean liner and the great ropes that held it to the city. It seemed strange to me that no else was walking toward it.

“What’s the first stop?”

“Bar Harbor. Then Greenland.”

“How long till you make St. Petersburg?”

“About three weeks.”

“Will there be Russians on board?”

“Let’s hope.”

She gave me a light punch on the shoulder, the way she used to, which somehow made me want to cry, and she said, “I really don’t see how you can afford this kind of thing.” I didn’t reply but imagined myself saying, “I’m what they used to call a gigolo,” and I pictured her bursting out in laughter, and I heard her laughter die as her eyes took on a sudden look of clarity, and I saw myself moving closer to her, saying, “It’s just business, Ma. I’m a businessman, too.”

Our farewell hug lasted a few seconds longer than I had expected. I believed she was sending me a telepathic message to tell me that she knew, that she understood, that she thought my way of life was not ideal, but that it was all right, given my particular skills and weaknesses, traits unsuited to running a business but sufficient for getting a person through the days more or less unharmed.

“If you can wait here, I’ll wave from the deck.”

“I’d like that.”

“It won’t be like the old days, when everybody waved handkerchiefs as the ship pulled away, but it’ll be close enough.”

“That’s O.K.”

It turned out I was the last passenger to sign in and step through security. A crew member told me I would have to go through the safety session with the other stragglers. I nodded and moved on to the gangplank.

The horn sounded, and from the top deck I saw my mother, thirty or forty feet below, holding her hands to her ears. I leaned over the rail and waved as the ship started to move, and she waved back with a wild hand. I remembered something, the white handkerchief in my jacket pocket, and I waved it with an old-time flourish, and I saw her laughing in a way that seemed to say she loved me, even if I didn’t measure up.

Jim Windolf has published short fiction in Ontario Review, Five Dials, Sonora Review, and a few other magazines. His humor pieces have appeared in The New Yorker, and his poems in Poetry Motel and Opium. He works as a journalist in New York.

Art by Bob Schofield @anothertower