Sleep Outside So Homeless Youth Don't Have To

Published on 23-11-2016

On Thursday, November 17th, in 18 cities across the United States and Canada, over 1,100 executives and leaders slept on the street, including Deepak Chopra, Brian Cashman, the General Manager of the New York Yankees, and former Wall Street executive James Manfredonia, for the purpose of supporting homeless youth.

All 3 of these men certainly have enough financial wealth to be able to simply write a check and call it a day, no?  What would motivate someone to voluntarily sleep on the street like a homeless person?  I showed up at New York City's Covenant House, on the evening of their annual "Sleep Out", to find out.

The Covenant House is the largest privately-funded agency in the Americas providing food, shelter, and care to homeless youth in 30 cities in 6 countries.  This charity organization helps kids get off the streets and create a better life for themselves.  

In preparation for a night of sleep on a cold New York City street, Kevin Ryan, the President of the Covenant House, explained the evening's mission to a room full of about 60 volunteers.  "This isn't a 24-hour exercise in pretending to be homeless.  It's so much more sacred than that.  This is you embracing their experience.  And for tonight, it's you being in solidarity with these young people, lifting up their dignity and their humanity".

During the event, I had a chance to catch up with James Manfredonia, a man who spent over 30 years on Wall Street, on the trading desks of highly competitive firms such as Merrill Lynch and Bear Stearns.  James has been on the Advocacy Board of the Covenant House for over 25 years, where his role has entailed everything from recruiting corporate partners such as Bank of America to mentoring the residents.  This is his 6th year in a row of sleeping out on the street. 

James Manfredonia getting ready to sleep out in NYC, November 17, 2016 

I asked James why he participates in the "Sleep Out", when he could easily just donate some cash and sleep in the comfort of his warm home in the suburbs.    

"Awareness", he said, "It's like the ice bucket challenge, that same theory of simulating what it feels like in order to bring awareness and spread the word.  It's doing more than just social media activism".  

What inspired you to get involved, James?

"The luck of where you're born should not disadvantage you in life.  It's how I've always felt.  Everyone should have an equal chance.  If you have the ability to help someone, you do it".  

How does it feel to be homeless, even for one night?

"The first night I was shocked", said James.  "I thought it would be like camping!  But then you get a piece of cardboard and a parking lot.  It's hard, it's loud.  It was way more severe than I expected.  You only get sleep through utter exhaustion".  

How do the kids react to all of this? 

"The kids are amazed!  A lot of them don't trust affection or caring.  So you sleep out to show the kids that there are people that care about them".  

What are the chances of getting more people from Wall Street to follow your lead?

"People react once you bring awareness.  Everyone participates.  Sleeping on the street makes people aware".

You represent a link between 2 seemingly different worlds.  How can we bring cooperation between the 2?

"People are people.  We can use the financial institutions to get more people involved".  

Has this shifted your perception of Gratitude? Do you feel more grateful for your own life experience?  


By giving back to the world - whether it be through financial donations, volunteer work, or raising awareness, not only are you helping others, but your efforts are returned to you exponentially in the form of increased Gratitude for your own life experience.  Generosity and Gratitude, in turn, have a positive effect on your well being and physical health.

"I'm grateful for every breath that I take and I want to share it with everyone", said Deepak Chopra, just hours before he rolled out his own sleeping bag on the New York City pavement.

As I listened to these teens tell stories of what led them to Covenant House - escaping physically and emotionally abusive homes, or drug-addict parents who neglected to feed them because they were too busy getting high - I realized more than ever how much I had to be grateful for.  And so do these kids.  Thanks to Covenant House, these teens are not only provided with the basic human needs of shelter & food, but they receive the emotional support and coaching they need to move their lives forward.  They can avoid a life of homelessness.  They can avoid the dangers of human trafficking.   I witnessed the excitement in their eyes as these kids told stories of job interviews and going back to school.  One young woman is working 3 different jobs as she prepares to start college in January.  She wants to be a neurosurgeon.  

I went home that night and felt more grateful than ever for the safety of my building, the heat in my apartment....for my warm bed.   And more inspired than ever to give back.  

Through compassion and enthusiasm, this year's Sleep Out raised $1.96 million to make a difference for at risk and homeless youth. If you'd like to get involved or make a donation to the Covenant House, visit for details.

Our associate Melanie Vangopoulos with Deepak Chopra