Jaileah Gibson, a 19-year-old at the Covenant House in the Germantown neighborhood of Philadelphia, told her life story to a group of community members, homeless advocates and a range of people on Thursday night.

The assembled audience members were all there to sleep out in the bitter cold to raise funds and bring awareness to the plight of homeless youth in Philadelphia and throughout the country. The message meshed with the event.

"People always say to me, 'You live in a shelter, but why are you always smiling?'" Gibson said. "It's just a mask and I'm going to keep wearing this mask until you get to know my story and understand it. I have only have told three people, and now I'm telling you guys."

Raising funds and awareness

Last year, Covenant House held a Sleep Out event in New York. It brought major executives, CEOs and other community leaders out in the cold to raise half a million dollars for homeless youth. This year, 12 Covenant Houses around the country are participating.

In Philadelphia, Thursday was the first-ever event. There, a candlelight vigil was held in the front of Covenant House where Jaileah told her story.

Then, Covenant House's Associate Director Hugh Organ read a list of names of homeless youth who had died this year in Philadelphia. Pastor David Maddox ended the vigil with everyone singing "This Little Light of Mine."

Gibson's story reminded many of the Covenant House staff and sleepers why they were bringing awareness to the issues of homeless youth.

She described the journey of her mother's battles with drugs, multiple evictions and her death while Gibson was living in the Covenant House. Today, Gibson works two jobs, is in school and is getting her own apartment in two weeks.

"She's unbelievable," said Heather Hansen, a partner in the law firm O'Brien and Ryan, LLC and one of Philadelphia's "sleepers." Hansen donated funds to the Sleep Out but also wanted to actively participate.

"I felt like it was a good opportunity to share just a little bit of their experience and take a little bit less for granted," she said. "They are so many things that we take for granted that kids like them are thankful for. Since I signed up for it, every night I get into bed thinking about how my bed is so comfortable and awesome."

A wide range of sleepers

Thursday night's "sleepers" ranged from senior executives at local banks to social media gurus, and Covenant House staff to Enon Tabernacle Baptist Church members and pastors, according to Janet Weyers, Covenant House's development director.

"The response has been amazing," Weyers said. "We currently have 17 sleepers and have raised $55,000. It's a really wide range we pulled together and they're all coming to support homeless youth in the community."

Cordella Hill, Covenant House's executive director, was also sleeping out.

Hill, who jokingly said she was hoping she would be able to walk in the morning, asked Wil Reynolds, a part of the Young Professionals Board at Covenant House, to join them.

Reynolds founded SEER Interactive, a web marketing and analytics company that has been on the Philly 100 Fastest Growing Companies for the last four years.

"I thought, 'How could I not?'" Reynolds recounted. "I think it's so easy to give lip service, myself included, to being involved and wanting to do things.

To walk in somebody's shoes and see what it's like for one night," he continued, "hopefully, it will help me get a better idea of what all the work I've been doing is actually for and what these kids are going through."

Other Philadelphia sleepers included Frank McGrane, Senior VP of Corporate Banking at Citizen's Bank; Terry Delaney, former financial executive at Sunoco and Covenant House board member; and Pastor Dr. Alyn Waller of Enon Tabernacle Baptist Church.

The "mask" of homelessness

In Covenant House's cafeteria, Sleep Out participants shared cookies, hot chocolate and stories with more of the youth as they prepared for the long night ahead.

The Covenant House provided the sleepers with cardboard, extra sleeping bags and red "goodie bags" filled with non-perishable snacks, hygiene products and emergency information. Those are the same bags they hand out to youths they find on the streets.

"I always considered it as a mask," said Jaileah Gibson, talking about homelessness. "I feel like I can finally take it off.

"The only reason I haven't taken it off is the fear of being judged," she continued. "For a while, I've been wearing this mask. Every day when I'm traveling on the bus and I see homeless people sitting on the corners ... that's my biggest fear. To be homeless to the point of living on the streets."

And out they went

The Covenant House parking lot provided sleepers a small taste of what living on the streets would feel like.

As the temperature dropped, sleepers set up their small spaces against the parking-lot wall, gathering layers around them, and sometimes huddled around the lights of iPads and e-readers.

It would be a long, cold night.

Pastor David Maddox gave the sleepers some final thoughts and blessings before they settled in.

"As you are out there, alone, and on a cold ground, think of our kids and how the community brought them, in various ways, here to us at Covenant House," he said. "And as you are out there, know too that you are in community, if that makes any sense."


Photos by Anna Flint for NewsWorks