I drove down from Phoenix on a Tuesday to ride along with the only window cleaner in a 4,800-person town. What he taught me about the trade had nothing to do with technique.
The road from Phoenix to Bisbee is four hours and twenty minutes if you do not stop, which I did, twice — once for gas in Tucson and once at a roadside taco truck near Benson that had a hand-lettered sign promising the best carne asada in Cochise County. Both promises were probably true. By the time I rolled into Bisbee proper, climbing the switchback into the old copper-mining town tucked into a fold of the Mule Mountains, it was a quarter past noon and ninety-one degrees in May. Roy Calloway was waiting for me in the parking lot of a place called the Bisbee Breakfast Club, finishing his coffee, leaning against the side of a 1998 Ford F-150 the color of dried sage.
"You found it," he said. He had the kind of weathered face that comes from forty years of southern Arizona sun, and a handshake that was firm but brief, like he had things to do, which he did.
Roy is sixty-four years old. He has been cleaning windows in Bisbee, full-time, since 1991. His business has no website, no Instagram, no Yelp page, no published phone number. He has 142 active customers. He has had most of them for twenty years or more. He charges, on a typical residential job, about half of what he could charge if he raised his prices, and he has not raised his prices in six years.
I had come to ask him why.
The first house was a small adobe on Brewery Gulch, owned by a retired schoolteacher named Marie. Roy let himself in through the back gate, which was unlocked, called out "Roy's here, Marie!" and got to work without waiting for a response. Marie waved at us through the kitchen window and went back to her crossword.
The Brewery Gulch house has fourteen windows. Most are small — two feet by three feet, original 1920s wooden sash, single-pane annealed glass thick with a hundred years of slight imperfection. Roy carried a five-gallon bucket, a t-bar strip washer, an Ettore squeegee with a brass channel that had clearly been rebuilt many times, and a single piece of scrim that he had folded into his back pocket. That was his entire kit.
He cleaned the fourteen windows, inside and out, in forty-three minutes. He charged Marie thirty-two dollars. He has been charging her thirty-two dollars since 2018.
"Marie's on the schedule for the Tuesday after Easter every year," he told me, walking back to the truck. "And the Tuesday before Thanksgiving. That's it. She doesn't call. I just show up. I started doing her place when her husband Frank was still alive, and Frank passed in 2009, and I have not missed a Tuesday since."
I asked him what would happen if Marie's house got dirty between visits.
He looked at me like I had asked him what would happen if the sun came up. "It does," he said. "But she doesn't see it. She sees that the windows look pretty good most of the time, and twice a year a man comes and they look better. That's plenty for her."
We did six houses that afternoon. The pattern was the same at every one. Roy let himself in, called the homeowner's name, got to work. There was almost no conversation about the work itself — no walkthrough, no quote review, no customer-service performance of any kind. The houses were the way they had been the last time he was there. The windows had the same problems, in roughly the same proportion, year after year. He knew which sashes stuck. He knew which screens to lift carefully. He knew which dog to ignore. At the fifth house, a woman named Janelle handed him a glass of iced tea without speaking, and he drank it in two long swallows and handed her back the glass without speaking, and she nodded, and the whole exchange took eleven seconds.
"She makes good tea," he said in the truck.
I had ridden along, the year before, with a route cleaner in Phoenix who served eighty-five accounts in a metro area of four million people. That cleaner spent maybe 25% of his working time on what he called "client management" — texting confirmations, handling re-bookings, addressing complaints, posting before-and-after photos, replying to Google reviews. Every customer relationship was a small constant maintenance.
Roy spends, by his own estimate, about twenty minutes a week on the equivalent. Most of that is calling people back when their phone breaks and they have to give him a new number. He does not handle complaints because he does not get complaints. He does not post before-and-afters because his customers already know what their windows look like.
"They've seen them before," he said. "And they'll see them again."
The economics, on paper, do not work. Roy is leaving money on the table — by my rough calculation, somewhere between $18,000 and $24,000 a year that he could pull in by raising prices to within shouting distance of the regional rate. Bisbee is not Phoenix, but it is also not 2008, and the cost of bread has gone up since the last time he changed his sheet.
I asked him about it directly. We were eating tamales from a place near the post office, on the tailgate of his truck, watching the late afternoon light hit the side of the canyon.
"My wife asked me the same thing," he said. He chewed slowly. "She would like a new roof. She would like to take a trip to see her sister in Oregon, more than the one trip we did last year. And she is right that I could pay for both of those things if I bumped my prices."
He took another bite. He looked at the canyon for a minute.
"But here's the thing," he said. "I have 142 customers. About thirty of them are over eighty years old. About fifteen of those thirty are on a fixed income that has not gone up in proportion to anything. If I raise my prices fifteen dollars, those fifteen people will stop having their windows cleaned. They will not switch to somebody else. There is nobody else. They will just stop. And then, in a year or two, when their house goes up for sale, the realtor will say the windows are filthy and knock ten thousand dollars off the asking price, and the family will lose ten thousand dollars to save the eighteen dollars I was going to charge them per visit. That math does not work for them. So I don't make them do it."
I sat with that for a while.
"And honestly," he said, "I make enough."
There are about forty-five thousand window cleaning businesses in the United States, depending on how you count one-person operations. Most of them, by count if not by revenue, are small. Many are very small. The trade press, when it covers the industry, tends to focus on the larger commercial operations — the pure-water high-rise specialists, the multi-truck residential franchises, the SaaS-enabled route-density optimizers. These are the businesses that grow, that get acquired, that make the conference circuit.
The Roy Calloways of the trade do not make the conference circuit. They do not get acquired because there is nothing to acquire — the business is the man, and when Roy retires the business will simply end. The 142 customers in Bisbee will, mostly, stop having their windows cleaned. A few of the younger ones will figure out the four-stage wash themselves. Most will not. Some will move into assisted living and not need windows cleaned anymore. Some will pass away. The town will go on, with slightly dirtier windows than it currently has.
I asked Roy if there was anyone training under him. He laughed.
"I had a kid for a summer in 2011," he said. "Good kid. Liked him. He went to NAU and became an engineer. Now he lives in Flagstaff and makes about four times what I make. I send him a Christmas card."
The light on the canyon had shifted to that specific Arizona pink that does not look real in photographs. Roy ate the last of his tamale and folded the husk neatly and put it in a paper bag.
"You ever think about what happens to the trade?" I asked him.
He thought about it for a moment.
"It'll be fine," he said. "There will always be people who want clean glass. There will always be other people willing to clean it. The arrangement we have now — me knowing 142 people, them knowing me — that part might not last. But the rest of it will."
He started the truck. We had two more houses to do before sundown.
Drew Giordano is a field correspondent for Window Washing Guide, based in Phoenix. He spends most of his time on rope and pole work but periodically takes longer reporting trips for the Field Notes pillar. He drove home that night and wrote this piece in his kitchen at three in the morning.