How One Uncomfortable Night Helps Keep Homeless Youth from Falling Through the Cracks

November 2017 will mark the third time that John Barclay, president and CEO of South Western Insurance Group Limited, has slept on the streets of Toronto. Organized by Covenant House, Barclay explains how participating in the annual “executive sleep out” addresses a dire need in the community. “There really is not a lot of structural support in place to help our city’s youth. Homeless teenagers represent “the lost middle” of the spectrum between childhood and adult programming.” Which is why, armed with only a sleeping bag and a piece of cardboard, he will once again join dozens of like-minded business leaders to generate much-needed funds and awareness. Barclay describes the sleep out program as both eye-opening and sobering. “Just walking through Toronto’s core,” he says, “you would never know any of that drug trafficking and sex trade was happening. It is literally like two different worlds occupying the same space - with one basically hidden in plain sight.” The sleep out raised just over one million dollars in 2016, and Barclay is hoping they will match or exceed that this year. “These are really amazing people,” he says of the youth he has met through his volunteer efforts. “They just need a safe place. If they can get that, they can get some balance back in their lives. No one chooses to be on the streets, yet as incredibly dangerous as it is, it is safer than what these young people have left. Most of us do not know what that is like.”