November 29, 2022

Sleeping Out with Covenant House

Sam Caucci

On November 17, exactly one week before Thanksgiving, hundreds of executives  from across the state took part in the Executive Edition of Covenant House New Jersey’s (CHNJ) Annual Sleep Out. 

For the fourth time in 4 years, I was one of them.

The idea is to raise funds in support of the organization, which provides critical immediate shelter for kids aged 18 to 21-years-old, and for executives to experience, for just one night, what 4.2 million American kids experience every night, by sleeping out on the streets.

We’re not exactly “out on the streets,” but that doesn’t mean it was easy.  We spent the night wrapped in sleeping bags, huddled in the private parking lot behind Covenant House’s Newark Crisis Center, under the protective watch of two cops stationed nearby.

It was an uncomfortable night for everyone, and first timers (like 1Huddle’s very own Mike Paintner, who came along for the ride) were easy to spot. 

As a returning sleeper, I’m savvier than I used to be. I’ve done this four years in a row, and I’ve had a lot of help along the way. 

During my first sleep out, a couple of the kids took pity on me, and showed me how to set up and angle the box I’d been given against the wind. Each Sleep Out since, I’ve gotten a little bit better at it; better at picking out my place on the lot, about how many layers I wear, and managing my discomfort. 

But what always surprises me, despite the police presence and the other participants nearby, is how isolating the experience feels.  

In the dark, in the cold, you sleep in fits. The city sounds different lying on the concrete and you’re more alert to the people passing by–  to every car that starts near you, every sleeping bag that jostles beside you; every tin can crash, or glass bottle break you imagine behind you, or around the corner. 

I feel vulnerable in a way that, frankly, I’m not accustomed to. Every year, that is the hardest thing to prepare for. 

But at the beginning of each Sleep Out, I try to keep in mind something I’ve heard Jim White, Executive Director of Covenant House New Jersey, say, more times than I can count, to the kids who pass through the shelter. 

“You can look back on this time,” he’ll tell them, “but don’t stare at it.”

There’s an element to those words that puts a lot of things in focus. 

The Sleep Out, the more I think about it, is itself an exercise in not “staring.” 

As participants we are encouraged to raise $5,000.00 if we can, but discouraged from making that our aim; to empathize with homeless youth, but not to believe that our empathy can grant us special knowledge– as though  one night in a parking lot cold ever  count as insight into what it’s like not have a home. 

It’s easy to focus on trees at the expense of the forest, especially if one of those trees can be held up as evidence of a good deed done; a goal achieved, a milestone reached. This might be true, especially in the corporate world, and especially in Q4. 

I had spent the end of September and the start of November between places, attending conferences, meeting customers, and schmoozing investors– first in New York, then in Miami; Detroit, LA, and, finally, Las Vegas, in a blur. 

There was some irony in that– after all those many days on the road— I had come home not to be at home, but to wake up half-in and half-out of a cardboard box.  

Still, looking back now, what strikes me is how nice it felt to be back in Newark, to wake up not far from the office, the company, and the life I have built here– and how relieved I was to go back to that life. 

The guilt that comes with that relief is complicated, and learning later that we managed to raise over $1.4 million for Covenant House doesn’t make it go away. But, like Jim says, best not to stare. 

I always like watching Jim make the rounds in the morning, as the sleep-out comes to an end.  Each morning after feels fresh and cold, and he is a welcome presence, patting bucks and checking-up on the rows of disheveled executives, still in their sleeping bags.

I pass him on the way out, and he asks, as he always does, how the night went.

Crappy as usual, is what I say.

“You’re welcome.” Is always his response. 

It’s one I’m always grateful for.

About 1Huddle

1Huddle is a coaching and development platform that uses quick-burst mobile games to more quickly and effectively educate, elevate, and energize your workforce — from frontline to full-time.

With a mobile-first approach to preparing the modern worker, a mobile library of 3,000+ quick-burst employee skill games, an on-demand game marketplace that covers 16 unique workforce skill areas, and the option for personalized content, 1Huddle is changing the way organizations think about their training – from a one-time boring onboarding experience to a continuous motivational tool. 

Key clients include Loews Hotels, Novartis, Madison Square Garden, PIMCO, TAO Group, and the United States Air Force. To learn more about 1Huddle and its platform, please visit

Sam Caucci, Founder & CEO at 1Huddle

You might also like... View more