Understanding homelessness first hand...Michael Johnson, Tim Metcalfe and Will Green are changed men and paying it forward.

Understanding homelessness is an important part of the job for Michael Johnson, CEO of the Boys & Girls Club of Dane County, in Madison, Wisconsin. So he set out to get schooled — by going undercover as just another one of the city’s 3,500 homeless individuals. He slept in shelters, panhandled on street corners and asked restaurants for free food, learning life-changing lessons — and helping a family of five get off the streets — along the way. 
“As a nonprofit leader I thought it was important that I understood the issue, so I can know how to tackle it,” Johnson tells Yahoo Shine about his two-night, three-day social experiment, which ended Nov. 15. Local market owner and philanthropist Tim Metcalfe, as well as Salvation Army Community Center director Will Green, joined him.
Their aim, in addition to raising awareness and learning about what homeless people truly experience, was to provide aid to an exceptionally needy case, which they were able to do for a mother of four. They found her living in an SUV in a Walmart parking lot with her kids, ages 13, 8, 7, and 1, and were able to immediately get the family into a hotel. Next they’ll provide a donor-funded apartment and pay the rent for two years, and Metcalfe will hire the mom to work at his downtown food market. 

“I was so happy to be a part of this, especially to be a part of really changing someone else’s life,” Green tells Yahoo Shine, adding, "I lived in poverty for a long portion of my life, so I really took this to heart."
The trio also filmed their experiences using hidden cameras and plan to release footage in the coming weeks after getting signed releases from participants. A Facebook post on the Boys & Girls Club page about the experiment has garnered more than 60,000 views since Monday, plus 1,500 likes and a slew of supportive comments.
The men say they were surprised to learn that many of the people sleeping at shelters had jobs, even cell phones, but that finding affordable housing remained elusive. But overwhelmingly, all three say that what they came away with most was a sense of the generosity in their community. Johnson, for example, went into a Perkins restaurant to ask for free food, expecting to be turned away, perhaps even angrily. “But this guy literally sat me down, gave me pancakes and bacon,” he says. “I was in tears. I was totally blown away by his generosity.”
Though sleeping and interacting with other homeless people and asking for handouts entailed all three men lying to people along the way, Johnson says he doesn’t feel guilty. “At the end of the day, we’ll be helping people, and it’s been getting the word out, so it was worth it,” he says. Metcalfe agrees, explaining, “What’s more important to me is what I learned, and it’s changed me. I have a completely different take on homelessness than when I went in.”
Homeless advocates generally tend to agree on principle, according to Michael Stoops, community-organizing director for the Washington, D.C.-based National Coalition for the Homeless. “How do you learn about homelessness? You can listen to a lecture, you can volunteer at a soup kitchen. But by hanging out with homeless folks at their same level, even if you reveal your identity, you can learn a lot,” he tells Yahoo Shine, adding that he applauds the three men for their efforts in Madison. “If it’s done right, it’s not an exploitative thing.” 
Stoops runs the coalition’s Homeless Challenge Project, described online as “Economically‑privileged people dressing down, emptying their wallets and spending time on the streets as homeless people.” He says he gets the word out mainly through outreach to students, vetting people to “make sure they’re doing it for the right reasons,” and making clear that the intent is beyond the idea of “homeless tourism.” (In Seattle recently, for example, homeless guide Mark Momany has been under fire for offering his Sub-Urban Experience for $2,000 a pop; the itinerary includes visiting “homeless gathering spots,” panhandling and sleeping in a shelter.)
Additionally, several schools and organizations around the country, including the University of Notre Dame Center for Social Concerns and Seattle Pacific University, organize undercover-homeless, or “urban plunge” social experiments for educational purposes.
Metcalfe adds, “People desperately want to help but are afraid. They think, I want to give money, but what will he do with it? I could see that in their eyes as they drove by us.” A solution, he stresses, is to support social-services agencies, which are doing a lot of good. “So my message is, this is how you can give. And you should feel good about it.”