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Sleeping Out with Covenant House

October 28, 2019 | by Jonathan Wasserstrum

On Thursday night, October 17, I joined more than 100 other real estate professionals in NYC and slept outside in a cold parking lot. I was participating in Covenant House’s “The Sleep Out” initiative. Covenant House advocates on behalf of homeless youth, giving them more than a meal and a comfortable place to stay — the organization provides tools, resources, and education to help the city’s most vulnerable young people to reverse their fortunes and to improve their life situations.

I became acquainted with this movement six years ago when a friend of mine recruited me to get involved. Combatting homelessness has always been a cause near and dear to my heart. At a young age, I was inspired by my mother, who was involved in similar work in Houston (where I grew up). I try to help out whenever I can, and I strive to make charitability a part of my routine: When I go out to eat, for example, I always take leftovers to give away to people I run into outside.

Jonathan Wasserstrum at Covenant House Sleepout: Real Estate Executive Edition

The Sleep Out began at 8 pm with orientation and programming. Several people from the organization welcomed us and highlighted all of the great work that Covenant House is engaged in. They then introduced a young adult who had come through their program. He spoke briefly about his personal journey, before taking out his upright bass and showcasing his immense musical talent. Since leaving Covenant House, he’s gone on to play at the Lincoln Center. You wouldn’t know walking by him, but he’s homeless.

From there, we had breakout sessions where groups of us met with high school-aged kids currently at Covenant House. We worked with them on mapping out possible professional paths and brainstormed how we could guide them toward success. At 10:30 pm, we grabbed our overnight bags and headed outside. We were given a sleeping bag, as well as a cardboard box to use as a pad. (When it rains, you get a garbage bag, too.)

Together, we raised more than $400,000 from friends and family, and raised awareness around NYC’s homelessness problem. This money will help fuel the solutions that Covenant House offers. I gave up one night of good sleep so that dozens of kids can do something meaningful next month and next year. Occasional sleepouts are just one of the many ways to get involved with Covenant House, a worthy cause.

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