At midnight, Lisette Lojo started her rounds at Penn Station. She cruised through the New Jersey Transit waiting area, past shuttered concessions selling pizza and magazines and headphones. She knew every inch of the place. She knew that down that corridor was where drug addicts gathered for some peace. She knew that under the stairs, where the heat gets trapped, you’d find older people fleeing the November chill. She knew you had to look in every elevator, under every bench. You’d be amazed where you found people.

Lojo was a social worker with the Bowery Residents’ Committee, a nonprofit contracted to handle New York City’s outreach to homeless people. When Lojo first joined the organization, as a member of the street-and-subway team, she worked forty or fifty cases at a time: people who needed help getting access to housing, social services, and more. It was what she had wanted to do ever since her parents divorced and her mother ended up single and poor in the Poconos, where Lojo grew up. One day, Lojo’s mother took her to a meeting about Section 8 housing vouchers, where they met a social worker who was exceedingly kind. Lojo wanted to help people the way that worker had.

Having delivered as a caseworker, Lojo was eventually promoted into management. She now ran B.R.C.’s transit work, but often accompanied her team on rounds. There were thousands of New Yorkers living on the streets, and B.R.C.’s job was to coax them into shelters, one at a time, slowly, laboriously, through the careful building of rapport.

Lojo, who’s just under five feet tall, was dressed in a light-gray jacket, skintight black jeans, and short boots. She walked up to person after person. On the rare occasion that she didn’t know someone, she would introduce herself: “Hello, how are you? My name’s Lisette. I work with B.R.C. Is there anything I can help you with tonight?” Walking through the N.J. Transit waiting area, she recognized a slow-moving older person who seemed consumed with transporting a grocery bag stuffed with essentials. This was Christian, who had spent time in and around Penn Station for several years. (All names of B.R.C. clients have been changed.) Christian, who was trans, could often be found in Grand Central Terminal during the day, migrating when that station closed. They had accepted placement several times but had a tendency not to last in shelters. They were more open to safe havens—facilities with lower thresholds for entry and, often, more privacy—as they felt more comfortable in smaller programs.

Lojo gently offered Christian a placement. They said no and resumed plodding down the hall.

In front of some monitors, commuters in overcoats were checking on the status of late trains home. Lojo stopped near them and warmly greeted Officer H., a policeman who worked Penn Station. Lojo prided herself on having a good relationship with cops. Whatever the country’s larger debates, in places like Penn Station, outreach workers and police worked together, though they had different goals, different training, and different specialties. Lojo’s job was to invite people into shelters. The police’s job was to enforce the rules of the station, which included not lying down to sleep. (You seemed to be allowed to live there as long as you remained vertical.) But both groups, in dealing with the same people night after night, often became fond of them.

Lojo checked in on her colleagues, who were already standing beside clients, working on placements. The B.R.C. workers all wore bright-orange jackets and clutched tablets that gave them access to thousands of case histories. When someone agreed to a placement, an outreach worker had to look them up: Was the client currently registered at a shelter? Were they new to the system? Then the worker placed a call to the Serious Incident Unit, or S.I.U., a hub run by the city’s Department of Homeless Services, to ask where the client could be sent. Many of Lojo’s colleagues were on their phones, waiting on hold.

For the S.I.U. call center, perhaps, each client was merely a name. But, for the outreach workers, it was important to push for a placement that had a fair chance of success, so as not to destroy a relationship that might have taken years to build. You had to know your clients, and know the patterns of past clients in similar situations, and think quickly and advocate. One client might have walking issues and request a maximum of one flight of stairs; you had to make sure S.I.U. didn’t send her to a place where that would be a problem. Another client might have a job with irregular hours, so you didn’t want a shelter with a strict curfew; you had to push for a safe haven or a stabilization bed, where the rules were looser. A person might refuse to go anywhere but Brooklyn. A person might need help taking meds, and so require a facility that was particularly attentive. There are more than three hundred shelters in New York City, and each of them has a personality, something to offer and something to avoid.

In the middle of the waiting area, a young woman wearing a beige overcoat and a handsome leather backpack, looking like one of the thousands of professionals in the station, stood with Lojo’s colleagues. They had pulled her file and found that she had recently been in a safe-haven facility, with her own room. They offered to have her taken back there, but the woman said she wanted to go to the Franklin Women’s Shelter. An outreach worker explained that, at Franklin, she would be in a dormitory, whereas in the safe haven she would again have her own room. The woman still wanted Franklin; she had found the room at the safe haven too small, too confining. The staffer called S.I.U. and was now on hold.

A short-haired woman with a denim jacket and a Nike backpack stopped by to greet the orange-clad battalion. Like an alumna offering an update for the class bulletin, she wanted to let them know that she had moved to a shelter in the Bronx. Lojo and a colleague combed through some corridors, looking for clients who might have nestled in remote areas. Her colleague went to a series of elevators to confirm that they were empty. People sometimes spent all night in elevators, even ones in service.

Now Alicia, a New York dame, drifted over to the orange jackets. She had long, perfectly coiffed silver hair tied back in a ponytail, and wore a slim-fitting leather jacket and black leggings. In tow behind her were two large suitcases, with a book lying across one of them—“Astor: The Rise and Fall of an American Fortune.” She had a brief interaction with one of the orange jackets, during which she claimed, repeatedly, that she had inherited an equity stake in Penn Station and, as a part owner, had a right to stay there.

Alicia was known to the B.R.C., but in general the outreach workers had to be careful about assuming who might be homeless. You could offend people by going only by clothing or demeanor; someone might just be trudging to their perfectly nice apartment after a long day at work. With practice, you began to register who kept walking past, back and forth, even if nothing about their appearance hinted at a problem. Maybe that guy had cheated on his girlfriend and been kicked out of the house. Someone lying on the floor could be battered by exhaustion or genuinely in need. You had to remain open. The B.R.C. workers all had stories of people telling them, “No, I’m fine, all good,” and then coming back later for help.

Around 1 A.M., Lojo walked toward the Hilton Passageway, originally built to connect the 1, 2, and 3 subway lines to the Hotel Pennsylvania, once the largest hotel in the world. It was a desolate corridor with limited foot traffic—a good place to catch a little shut-eye if you were avoiding police officers. She saw two colleagues crouching beside a client named Peter, who, to the untrained eye, might have seemed asleep. But the B.R.C workers knew Peter; he was drifting in and out of awareness, but he could hear them, they were sure. Next to him were a pink paper coffee cup and a baby bottle. Peter was in his sixties or seventies, with gray hair and glasses. His face was red and blotchy. The orange jackets knew he struggled with alcohol, and they were trying to entice him into a shelter yet again.

Peter asked for Sharon, a caseworker he liked from an earlier shift. He wasn’t pleased to learn she had gone home. Every so often, his legs kicked out and swung back in. He had a hospital bracelet on his wrist. According to a search of the database, he was registered at Kingsborough Star shelter, but he refused to go back there.

A worker’s phone rang. S.I.U. had found a bed at Jack Ryan, a shelter not far away, on Twenty-fifth Street, which belonged to B.R.C. A good fit.

“Peter! Jack Ryan. We got a bed for you. Jack Ryan,” the outreach worker said.

Peter suddenly seemed asleep.

Lojo tried this time. “Come on! Come on!” Peter was barely responding. The B.R.C. workers were generally discouraged from touching clients, so they had to use their voices. This wasn’t working. The two orange jackets rattled a nearby metal barrier to wake Peter up. This worked just enough to get him to say he wouldn’t go.

Lojo and her colleagues conferred. It crossed her mind that Peter might be in bad enough shape that she could pursue involuntary removal and transport to a hospital, known in the field as a 9.58. In recent years, New York City has made it easier for social workers to do this, by clarifying that the requirement for removal goes beyond a subject posing an imminent threat—whether to others or to themselves—to a subject’s mental illness leaving them unable to provide for their own needs. But, on inspection, Peter was responsive, sort of; he was engaging, sort of; he wasn’t as bad as they had seen him. Lojo was happy that he had at least found this stretch of corridor, which was warm.

She noticed a squadron of cops for the Metropolitan Transportation Authority heading toward them. “Hey, Peter, the police are coming through,” she said. “You want to come with us to Jack Ryan? We got your shelter bed ready. It’s really close by.”

The cops arrived and compared notes with Lojo and her colleagues.

“Peter! Peter, you want to go to Jack Ryan?” one of the officers called out.

“No!” Peter answered, more authoritatively than before.

“Come on! You got to get up, though.”

One of the cops stage-whispered to another: “Does the same thing every day.”

Now Lojo crouched down. Peter roused again but had grown more certain since his last utterance. He glared at the officers. “I’ll put my foot up your ass,” he said. “I’m not going anywhere.”

The officers surrounded him, jovial but firm. He had to get up, they insisted. And he should go to Jack Ryan, though it was his choice.

“I’m not going anywhere,” he said. “Twenty-fifth Street sucks!”

“What?” a lanky officer said. “It’s a five-star hotel!”

Peter was fully awake now. The police warned him that they were going to pick him up by force.

“One, two, three—there we go.” They lifted his body, which was swathed in a black trenchcoat. Now Peter was standing, and the officers were joshing with him. Oh, Peter. Always the same with ya, Peter. One officer knew enough to ask if Peter had his usual supply of peanut butter on him. He did. He pulled a jar of Skippy out of his trenchcoat pocket, fished a green plastic spoon from somewhere on his person, and gave himself some fuel.

The police, satisfied that he was no longer lying down, bade him farewell. Lojo and her team said their goodbyes, too, reminding him to get in touch if he changed his mind about shelter. Peter probably had another good hour to sleep before the police came through on their next round.

Lojo understood why people wanted their freedom. Some had been in prison and heard that shelters were no different. Others had already been in shelters, and been assaulted, sexually harassed, or robbed. Lojo worked to get people into the system, but she didn’t judge them for saying no.

Just after 1:30 A.M., she walked outside to Penn Proper, which was what the orange jackets called the block surrounding the station. She did a loop looking for people who were sleeping outside in the cold. Across from a sports bar on Thirty-first Street, she came upon Ray, whom she knew, sleeping against an orange-and-white concrete barrier. He was wearing several jackets and had a hood over his head. Lojo woke him gently. At first he was startled, but then he smiled and cheerfully told Lojo that he was fine, thanks.

She made her way around the block and ended up at the station entrance at Eighth Avenue and Thirty-first Street. There she saw two colleagues talking with the woman with the beige overcoat and brown leather backpack. The woman had been granted a spot at Franklin, and the pair were waiting with her for a transport vehicle.

Officer H., tall, strongly built, a little rotund, was still cheerful as 2 A.M. approached. He was standing guard at the station entrance. After a certain hour, it seemed, people needed a train ticket to enter—likely an attempt to limit the homeless population inside. A drunk man with spiky hair, holding an extra-tall can of Modelo, was repeatedly walking up to the woman in the beige coat and staring at her, as if she were a museum piece. She would move; he would follow. One of the orange jackets waiting with her waved at Officer H. He walked over from his post and told the drunk man to leave. The man stumbled and muttered something in Spanish. Then he hissed at Officer H., “What’s your problem?” Officer H. repeated his command to go away.

“What’s your problem?” the man kept saying.

Move along.

“What’s your problem?”

The drunk man now lost interest in the woman in the beige coat, who was getting into her transport vehicle. His fly unzipped, the Modelo can dangling from his hand, he refocussed on Officer H. He seemed to decide that the best way to provoke the policeman would be to try to enter the building.

Officer H. grabbed the man’s beer, turned it upside down, and emptied it on the pavement. The man drifted away.

A few yards away, one of Lojo’s colleagues had brought her a young guy with long hair, visiting from Canada. Something had gone wrong with his train back home. He was stranded in New York, and he didn’t have the money for a hotel. He was homeless, temporarily.

Lojo figured that a drop-in facility, where people could sleep in a chair for the night, with access to a hot meal and a shower, would be perfect for him. He wouldn’t have to deal with the rigmarole of formal intake. She called the facility.

As she waited on hold, the city night buzzed: people getting drunk, getting food wrapped in foil, going home. Officer H. noticed a man advancing toward the station at a clip. When the man was maybe thirty feet away, he thrust his arms out, as if about to give a hug, and continued his running advance. Officer H. thrust his own hands forward in preparation for the looming collision. “Shorty!” he called out to the man, laughter and familiarity in his voice.

Shorty careened into Officer H.’s body, gripped his arms, and began wiggling to try to get past him and into the warmth of the station. The policeman held on to Shorty’s biceps and shook them slightly, both giving the sense of a loving embrace and using his strength to lift Shorty ever so slightly off the ground and clear of the entrance. On the verbal plane, nothing about Shorty’s attempt and Officer H.’s blockage was explicit; it was just “Hey, Shorty!” and “How ya doin’, man?” and “You been good?” But on the physical plane, Shorty had tried to use a hug to sneak into the station, doing what he had to do, and Officer H. had thwarted him, doing what he had to do.

Meanwhile, Lojo had managed to get the stranded Canadian assigned to a facility, before learning that a homeless woman downstairs had spit on and pushed an outreach worker. Lojo thought she might need to assist with her first forced removal of the night. She went back inside, only to learn that the woman had darted outdoors. It was 2:15 A.M., and the waiting area had a more trippy feel than before. People were talking to themselves, doing yoga poses, trying to sleep. Lojo spotted a man who had been about to carry a bicycle up the stairs when he appeared to fall asleep hunched over it. She woke him, introduced herself, and offered help. The man barely seemed to register her. He lifted up his giant bike and simply resumed his climb.

Lojo continued her rounds. She strolled past some monitors advertising trains to Long Island, and there, in a broad passageway, she ran into Christian.

Christian again declined help, explaining their preference for sleeping wherever they pleased, however they pleased, and not in a shelter. “I want my own rest, quiet, no one bothering me,” they said. They wore a plaid fleece jacket and two wool knit caps. They had come into a container of takeout food, which hung from their hand.

The first time Christian had refused services, at midnight, Lojo had taken the answer at face value and moved on. But now, more than two hours later, Lojo tried to keep them talking. She patiently listened as Christian spoke, her face showing neither agreement nor disagreement, only that she was paying attention. Christian, sensing that they had an audience, began to give something of a sermon, which was hard to follow. We don’t have time, Christian said. If you want to find out God’s true colors, read the Bible closely. It’s all in there. What do people want?

Lojo nodded. She thought of a non sequitur that might work: Did Christian want to try a single room this time?

No, Christian said. They didn’t want to be among those boys. In fact, they needed to get out of town. Could Lojo help?

Lojo said that there was a program to buy bus tickets if you had a place to go.

Good, Christian said. The place they needed to get to was on another island, the name of which they couldn’t remember, but they knew there were theatres on it. Maybe, Christian felt, beyond Staten Island, just past it.

Lojo was trying to remain open to the possibility that the island Christian was referencing was real. Christian said it contained a city that some people called St. Andrews. As Lojo picked up her phone to look up the name, Christian hastened to add, “I don’t know if it’s written down. I don’t know if it’s in your categories.”

Now Christian clarified that, in addition to being just beyond Staten Island, this island was in the Caribbean. They longed to go back there, but there were too many boys there. The boys, they bother you. Christian had a faraway look in their eyes.

Lojo nodded her percussive, patient nod. Christian was not in danger, but she relied on these extended conversations to evaluate whether someone had “decompensated”—declined psychologically—since she had last seen them, maybe even to an extent that merited forced transport to a hospital for evaluation. Christian was talking about how airplanes to the island weren’t safe. There were guns, knives, razors. Lojo continued to listen and nod.

Now Christian provided an opening. They really could use a shower. They weren’t interested in shelter, but a shower would be great. So would clothes. Could Lojo help them get pants with a thirty-one- or thirty-two-inch waist? Lojo said that the morning team could bring them clothes. They could go to a facility where they could wash and change and feel fresh. Christian liked this plan. On her tablet, Lojo noted the general area where she had encountered Christian—Tracks 20 and 21—and typed instructions to her team. By the end of the night, B.R.C. would record thirty-four contacts with potential clients and, of those, twenty-three who agreed to accept services.

In Lojo’s line of work, you had to leave people the space to come to you. “You may be the only person that this person spoke to today,” she said later. “So when they’re wanting to talk about something that has nothing to do with housing, maybe it’s just a way for that person to connect with someone. We always tell our teams, obviously housing is important, housing is the focus, but housing doesn’t need to be the only conversation. The person’s not willing to talk about housing, but—I don’t know—they like the Yankees. Talk to them about the Yankees, and maybe you could say, ‘Hey, we actually have a facility that’s up in the Bronx by Yankee Stadium, if you wanted to check it out one day.’ ”

“The decision for someone to go in,” she added, “is not yours. It’s theirs.” ♦

This is drawn from “Man in the Mirror: Hope, Struggle, and Belonging in an American City.”