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Metro Winnipeg editor learns at the CEO Sleepout

Lucy Scholey found the CEO Sleepout is largely about meeting people, hearing their stories and providing support.

Brad McMullan, a Winnipegger who has been homeless for 17 years, at the CEO Sleepout in downtown Winnipeg Oct. 26, 2017.

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Brad McMullan, a Winnipegger who has been homeless for 17 years, at the CEO Sleepout in downtown Winnipeg Oct. 26, 2017.

Many of us were prepared to sleep on cold concrete.

We wore winter coats, long johns, toques and mittens. We unrolled sleeping bags outside the RBC Convention Centre. A few people even pitched tents and brought extra pillows.

The group of roughly 80 executives, politicians, anti-poverty advocates and community leaders, myself included, were ready for the CEO Sleepout.

But many who live on the streets weren't as prepared for the sudden burst of winter. A box of donated clothing emptied quickly and 234 backpacks filled with supplies were handed out. A long lineup formed beside a nearby Salvation Army mobile truck serving coffee and soup.

The CEO Sleepout is partly meant to raise awareness of the very people who need warm clothing and hot meals. It has raised more than $880,000 in its sixth year and End Homelessness Winnipeg is still vying for that $1-million goal. The funds go towards employing homeless people. This year, the event moved from September to October to coincide with the National Conference on Ending Homelessness taking place in Winnipeg.

I’ll admit, I was skeptical of the CEO Sleepout.

My hesitations had nothing to do with the fundraising or the good intentions of those participating.

To me, it felt like a disingenuous way to sympathize with homeless people. One night outside does not seem enough to address the complexities of street life.

Also, this experience was relatively safe. A block of York Street was closed to traffic, with security patrolling end to end. Boxes of pizza piled high on nearby tables and the Salvation Army truck was handy all night.

Despite the cold, it still felt more like urban glamping compared to the reality of life on the streets.

But I learned the CEO Sleepout is largely about meeting people, hearing their stories and providing support.

Brad McMullan, a Winnipegger who has been living on the streets for the past 17 years, has been to every sleepout.

“It’s introduced me to a lot of good people,” he said, after insisting I take one of two cinnamon buns donated to him.

Some sleepout participants sat around a sacred fire late into the night. Volunteers kept it lit during the three-day conference, which focused on Indigenous homelessness. It offered a circle of support and storytelling – a simple act of warmth both literally and figuratively.

Many people with lived street life experience stuck around for a while, eating pizza and watching movies on a big-screen projector. It was their night, after all.

My earlier reservations about the event seemed irrelevant, especially after hearing Al Wiebe, a formerly homeless Winnipegger, describe his past experience as losing the “absolute will to live.”

“Life on the street is one of the most difficult things you can ever imagine.”

Later that night, I burrowed myself in my sleeping bag, drawing it around my head like a cocoon. I was still cold underneath all those layers.

As I tossed and turned for four hours, I tried my best to imagine that life.

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