A CEO’s Journey Into Homelessness

CEO Eric Weires sits on a bench and displays his sign. Sign reads: “3 Kids. Just wana get home. I’d Appreciate the help!”

Kate Glantz

This is a story of compassion in unlikely places. Of men with very little and men with a lot, doing right by each other because it was the right thing to do. This story begins with Eric Weires, a soft-spoken man from the Midwest with kind eyes and an easy way.

On May 4, Weires left his family and comfortable life in Chicago for a weekend of sightseeing in Washington, D.C. Although he intended to visit many of the nation’s most famous museums and monuments, Weires was not your average tourist. His to-do list also included sleeping on cardboard, sampling the cuisine at local soup kitchens and panhandling.

As CEO of Fine Line Services, a Chicago-based maintenance company, Weires was in town to take the Homeless Challenge, a project designed to let Americans experience the realities of homelessness. The National Coalition for Homelessness has led Homeless Challenge Projects in Washington for more than three decades, and for 48 hours, Weires — the first CEO in Challenge history — would live on the streets penniless and with no guarantee of shelter.

Although the Challenge itself was a new experience, Weires was no stranger to hard times. As a child he thought of homelessness as more than a remote possibility.
“It was always stressful and humiliating and something that always was around the corner. Thankfully, it never happened to me as a kid. But it was rough growing up, real rough.”

Weires viewed the Homeless Challenge as an opportunity to raise the profile of an issue close to his heart and renew a greater sense of appreciation for his own life and how far he has come.

Besides photo identification for security measures and his cellphone to update a video blog, he carried only a map of the city, a checklist of activities representative of homeless life, and a shiny, black industrial-sized trash bag.

Day One began with a walk down Embassy Row. After a brief detour getting lost in Rock Creek Park, Weires located the Capitol and headed downtown. Making progress on his checklist, he stopped at an upscale hotel to request scissors and cardboard to make a sign. He was relieved when the concierge obliged.|

After a brief internal debate about how best to frame his appeal, Weires scribbled in blue Sharpie marker: “3 Kids. Just wana get home. I’d appreciate the help!”

He camped out on a corner near the White House and collected $20 within an hour. Taking a passive approach to panhandling, Weires did not exchange a single word with anyone walking by. He was invisible, but he would not go hungry.

Making concessions for others and his own past behavior, he mused, “Who has time to start a conversation with friends [on the street], much less a homeless stranger? There are too many. You would have to stop on every corner.”

Weires tucked his sign into his pocket and headed to Subway for an early dinner.

As night fell, he met up with his homeless guide, Andre, at Franklin Square Park on 14th and I streets NW.

While Andre is a full-time student on scholarship at a local university, he has no source of income beyond what he earns guiding Homeless Challenge participants so he cannot afford to move off the streets.

The night was cold and the bench was hard. This was expected. What Weires did not anticipate were the enormous rats skittering below his feet. For the first time that day, Weires was ready to pull the plug.
Fortunately, Andre knew of a “nice alley” behind a nearby hotel, which was well kept as alleys go. The men pulled cardboard from a dumpster for makeshift mattresses and settled in for the night.

After a few fitful hours of sleep, the two parted ways as the sun rose. Weires was suddenly faced with the gravity of what he described as “the endless day.”

“There’s tons of time. It’s a little daunting, man. This just goes on forever. If I had to do this for a week, month, year or multiple years … I can see where others lose it.”

Weires also reflected on the chore it had been to locate public restrooms throughout the city. An obstacle, he noted, that could be even more stressful for women. “Even McDonald’s locks their [bathroom] door,” he said.

But compassion was also found in unlikely places. “[That morning] I went into a Starbucks and they were really nice. So nice that I asked them if they wouldn’t mind giving me a cup of their joe. So I got a free Starbucks,” he said.

Feeling positive despite his aching feet, Weires trekked across the city, with $12 remaining and his trash bag in hand. He spent much of the day alone and in silence. Glancing at the bag, he said, “At first it was a little embarrassing, but 99 percent of people didn’t notice me.”

Around 9 p.m., Weires met his second homeless guide, Steve, a self-professed “mother hen” of Homeless Challenge participants who classifies himself in the upper echelon of homelessness. In exchange for housing, he lives with and cares for an ailing senior citizen.

Weires and Steve made camp in an apparently rat-free park on Pennsylvania Avenue. The park bustled with other homeless men and women who for myriad reasons were not sleeping in one of the District’s shelters.

It was another cold and windy night. With his shoe as a pillow, Weires was comfortable enough but could not stay warm. No stranger to cruel elements in the middle of night, Steve had an extra blanket, which he tucked around Weires as he slept. The night passed without incident.

Eager to escape the morning chill, the men made their way to the Church of the Epiphany on 13th and G streets, a place of worship and refuge for anyone in need. Sensitive to extremes of both of weather and circumstance, the church opens its doors at 7 a.m. every Sunday with offerings of Bible study, support groups and a warm meal.

[Disclosure: Street Sense Media rents office space from the Church of the Epiphany]

In his final act as a Homeless Challenge participant, Weires used what cash remained from panhandling to buy a gift card from McDonald’s. In less than a minute, the card was handed off to a man in need.
As his weekend peers ambled along another eternal day, Weires slipped off the street as quietly as he had come.

Weires entered the challenge to help shine a light on the untold burdens faced by homeless people in America. For two days, he was largely invisible and powerless, his thoughts and talents masked by rumpled clothes and empty pockets.

But as a corporate executive, Weires’ recognized he has the platform to be a catalyst for change.

Region |Washington DC

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We believe ending homelessness begins with listening to the stories of those who have experienced it.