11/21/2013 11:12 am ET Updated Jan 25, 2014

My Experience Sleeping on the Streets of New York

Three years ago Strauss Zelnick asked me if I would participate in a Covenant House event and sleep out on the streets of NYC in solidarity with homeless youth. I asked no questions. I said YES.

I am pretty sure he assumed my instant YES was because I am a kid advocate. And of course I am and that was part of it. But I had been curious for many years about what it would be like to be homeless and have to sleep outside in NYC. I had resigned myself to not having the courage to find out for myself. Strauss handed me an opportunity to do so. Here is what I wrote right after my first time participating in a Covenant House sleep out:

I didn't really think about the location until we were walking down 41st Street past the tunnel entrance, through construction sites blocking the sidewalks.  Covenant House lives in a tough neighborhood -- there is nothing welcoming about it, except when you get past security and enter the doors.

They know how to take you in. Right away you get the secret of Covenant House and why it is successful. They respect each individual for who they are and who they can become.
Condescension is not on the vocabulary list. It is a serious place with a serious mission and a very funny man running it: Jim White. The combination is effective.

We found ourselves talking to Lee, a 22 year old from Palm Beach FL, who spent most of his childhood in an unstable home. He changed schools, "to match birds coming and going with the seasons," went to school to be fed and graduated with a 3.8 average. I asked him, "How could you do so well in school when you had no real home?" He told me, "I figured I was there I might as well make the most of it."  He wants to go to Hunter College and study early elementary education. He was so smart, articulate and full of appropriate quotes where he couldn't always remember the source but always relayed the sentiment.  

During the event, we mingled with other CEOs. There were executives from Madison Square Garden, Goldman Sachs, Hudson Bay and NBA. We were certainly the oldest campers, but we have really good gear (My husband Kit bought me long johns on his lunch hour and a really warm hat). I don't drink anything because no alcohol is allowed or served and I didn't want to have to go to the bathroom in the middle of the night.

They show a video that their staff and kids made. It features Louis who is incredibly photogenic, articulate and smart.  He takes us to the corner that he slept in for weeks, just outside a subway stop and relives the feelings and the fears.  We know that we will feel the pavement Louis felt and the cold, that we will hear the noise of the city but that we will not feel his fear. This is not your traditional fundraising video. The video ends with a montage of Covenant House kids being told that a bunch of CEO's are going to sleep outside in solidarity to them. They can't stop laughing.

They break us up into groups and people sit in a circle. Five CEOs and three kids from Florida, Georgia and LA.  Charles grew up in South Central LA, he'd been shot by the time he was 12. A "kind" stranger took him out of the gang neighborhood and transplanted him in Palos Verdes and then began to sexually abuse him. He lived homeless on the streets and got a part time job, saved enough money to get a ticket to LGA and made his way to NYC. Homeless in NYC on arrival, he found his way to Covenant House. He went through the program, got on his feet, graduated and now has a job as a fashion stylist (he was wearing a fantastic sweater and dashing scarf). He gives back to Covenant House. His positive outcome gives Covenant House residents hope.

It is 34 degrees outside. We have our Patagonia down sweaters, outer coats, long johns, heavy socks, gloves, hats. We make our way outside. Unfortunately, we lingered inside a little too long and the premium spots along the wall are all taken. We squeeze our two bags in between rows, inches from other bags. I had imagined when they said cardboard boxes that I'd be sleeping inside a refrigerator box. No such luck. We're given two boxes to sleep on top of.  

It is cold and that pavement is hard. Here are somethings that I notice all night long -- it is really noisy. First the jack hammers of the nearby subway construction, then the fire engines, trucks and buses. That tunnel entrance out front draws in traffic all night long. I sleep with my phone and check the time frequently. I sleep for about 20 minutes every hour, I am alive to my surroundings.

I also notice that there is a reverence to the experience on the part of these CEO's. No one is making light of this. We are orderly. We don't toss and turn. We stay put. The CEO solidarity sleep out is just that. By six am most folks are up and circulating. I hope I can hang onto the lesson about respect for all. Honestly this morning, it feels like to solution to all the world's problems. I feel it in my bones.  

The second year, I said YES to Jim White as quickly as I had to Strauss. My experience with Jim is YES is the only real option in terms of answers. When you see what impact he has every day of the year, one about to be sleepless night is not much.

The kids I met were just as memorable. But honestly the sleep out tone changed. These were folks who knew how icy cold the pavement is, how they wouldn't sleep and they returned. These were folks who were connected to the other sleepers through admiration for the kids and Covenant House. No one wanted to bed down. We talked for hours.

Because I was a veteran sleeper, I knew to get out there early to secure a cozy spot. Live and learn. I saw this lovely slope..ah, it looks like a pillow. This will be fantastic. I am on a ramp. Turns out ramps are not a smart choice. Sleeping bags are slippery. The gentleman at the bottom of the ramp was kind and a little amused by my gradual and constant slipping. I did not sleep at all that night.

My third year, see above. Turns out I am a Covenant House advocate. Thank you to all of my friends who have supported me over the years. And thank you Covenant House for helping the comfortable feel uncomfortable.

This post was previously published on Geraldine Laybourne's blog.

For more information on Covenant House's Sleep Out, visit here.