Milton Chalmers can't see the Chicago skyline from his modest bedding underneath the iron framework of Lower Wacker, but it doesn't stop him from thinking there's a place for him beyond Skid Row.
"I want to be in the Army," said Chalmers, 21, who has been homeless for two years. "They said I'm still young enough to join."
All Chalmers' owns is in a pile on the sidewalk: a couple of blankets, pillows and clothes. He doesn't go to well-trafficked spots to panhandle. Almost every day, he stands on his stretch of two cement squares, leaning on a steel beam, hoping a kind soul hands him a dollar, maybe five, if he's lucky.
On a recent January night, he was greeted by a different kind of visitor. The city's Department of Family and Support Services worker, outfitted with a pen and clipboard, spoke in a gentle, yet sincere tone to learn about his situation.
For the first time in the department's federally mandated count of homelessness, the agency appointed a special team of formerly homeless youths to interview unaccompanied young people like Chalmers.
Tyshon Shepard, 24, who has struggled with homelessness since he was 18, was one of the volunteers.
"For me, it's not hard to connect with them," Shepard said. "I use my personal experience, and I draw them in to see if it's OK to refer them to a certain program."
While 300 volunteers and 150 city workers fanned out to nine designated locations across Chicago, Shepard and roughly two dozen volunteers who were formerly homeless youths were given free rein to search the city.
"They're the experts," said Adriana Camarda, the department's chief planning analyst. "We want to improve the methodology, because some groups don't want to be found, but we want to find them to help them."
The youth team began at the city's four drop-in centers, which are not shelters, but serve as daytime locations where young people can find basic necessities, such as food, showers, laundry facilities and clothing.
"It's a young person talking to another young person who's had the same life experiences," said John Pfeiffer, the department's first deputy commissioner, who led a team surveying homelessness in the Loop. "So, we break through a lot of barriers immediately and get a lot more direct communication."
The count, required by the U.S. Department of Housing and Urban Development and Chicago, along with other major cities, tallies and interviews people with temporary housing situations. This includes those living on the streets, in shelters, on public transportation, in parks and in cars. It's generally conducted in the last two weeks of January, typically the coldest time of the year, to get the largest count of homeless people in shelters. This year, Chicago placed special attention on young people by extending the hours to search for and survey those 24 and under.
"It's obviously unacceptable that any young person should be left out on the streets when their social support network doesn't function well," Pfeiffer said. "We want to be there for them. ... In order to do our best work we are really anxious to have the best numbers possible."
A city of Chicago count conducted in January 2014 found 6,294 homeless individuals: 5,329 in shelters and 965 living on the streets. Young people, 24 and under, make up 41 percent of the population in Chicago shelters and more than 8 percent on the streets.
In the case of the young homeless, many run away after experiencing abuse at home. Others are kicked out by their parents for a number of reasons, including becoming pregnant or for their sexual preference. For Chalmers, growing up in Humboldt Park, gang affiliation was his downfall.
"I used to hang out with a bad crowd - gangbangers," Chalmers said. He joined the Latin Kings at 14 and began selling cocaine. "I was like, I'm finally hanging with the big dogs," he said. "I was getting money, cars and girls."
All of that came to an end in October 2011 when Chalmers, then 18, was stopped by Chicago police while walking with two friends in Humboldt Park. The officers found him with a gun. Chalmers pleaded guilty to weapons charges and served nearly three months in jail. During that time, he said he decided to stay away from his former gang and selling drugs.
"I went to jail, and when I got home my parents kicked me out. They didn't want to deal with that. I tried looking for a job ... there's no jobs and nobody around."
With nowhere to turn, he wandered around the city until he came across a stretch of homeless people under Lower Wacker near Columbus.
"I just walked past here, and I was like 'I found me a spot,'" Chalmers said.
He's been in and out of jail for trespassing at least three times, most recently last month when he also picked up a misdemeanor charge for marijuana. After seven days in jail, he was back on the streets.
Chalmers' section of sidewalk is just one of a dozen on Pfeiffer's list of areas frequented by the homeless.
A short distance away, Pfeiffer and another worker found a young man sitting cross-legged on a piece of cardboard in a Zen-like state between two concrete pillars in the median of the road. A few feet away, sanitation workers hurled garbage into a dumpster, drowning out the antiquated radio playing at his feet. But the man, who wore a stained, brown jacket and no shoes, remained still, staring at a graffiti-covered wall with misspelled messages like "Homelee people core, do you?"
Pfeiffer approached the man and crouched down: "How long have you been down here?"
The man, who appeared to be in his 20s, calmly responded: "It feels like forever."
Pfeiffer asked again. "Since '07," the man answered, prompting a HUD employee to blurt out "My God ..."
The man was unclear when asked his name and age, but he stirred when asked about life on the streets.
"It's hard out here," he said, head bowed, contemplating which secondhand cigarette to smoke.
Pfeiffer jotted down the man's drug use and apparent mental illness on the survey worksheet.
"(On) Lower Wacker we saw typical scenarios, we saw typical chronic illness, people in the criminal justice system and foster care a long time ago," Pfeiffer said. "These are folks we are really trying to help."
Pfeiffer said he hopes volunteers will be able to poll at least 10 percent of the homeless people on the street to create an accurate snapshot of homelessness in the city.
The department anticipates the most accurate picture of homelessness the city has to date as this will be the first time counts have been conducted three years in a row. The tally, which will be released in the summer, is generally conducted every two years. After 2013, Chicago voluntarily participated in a federal count focusing on the homeless veteran population.
Shepard admits that when he was younger, he would try to hide the fact that he was homeless. But now, he sees himself as a mentor, telling stories on how he overcame life in group homes and "couch-surfing" by applying for low-income housing on the Near West Side.
"Being in their shoes, I try to put a smile on their face so they can say that person helped me," said Shepard, who's taking classes at a local culinary school. "They're looking for someone not just to pull you up, but who will walk with you."
@_tonybriscoe