Originally published on my LinkedIn in December 2019.
On December 7, 2019, I spent the night sleeping outdoors in Times Square.
Not by necessity, but by choice. I was participating in the Big Sleep Out, a charitable initiative where thousands of us slept outside to raise awareness and funds for homeless services.
This is what I learned.
Why I Participated
When I learned that Ascential, the company I work for through WGSN, was organizing a team for the Big Sleep Out, I was interested but hesitant. I’d donated money to causes before.
Did I really need to spend a night on the street to prove I cared? Then our company president, Philip Thomas, made it personal. He asked—
Why donate if you don’t understand the problem?
That question stuck with me. I realized I didn’t actually understand homelessness. I had statistics in my head but no real sense of what it meant to sleep on concrete.
Before the Night: Education
I started researching. Nearly 1 in 121 New Yorkers are homeless. That’s a staggering number for a city I live in. But statistics don’t tell you much.
I talked to a friend named Antonio who’d worked with homeless populations. He told me something that changed how I thought about this: people don’t become homeless for one reason. Some lose their jobs. Some age out of foster care. Some face a temporary crisis that becomes permanent.
And here’s the part that hit me—shelters aren’t the end goal. They’re the bridge. The real goal is helping people transition off the streets and back into stability.
The Night
From 10 PM to 6 AM, thousands of us lay down in designated zones in Times Square. We had sleeping bags, emergency blankets, and donated supplies. Will Smith performed beforehand. Tourists walked past. And then it got quiet and cold.
I wore layers. Good layers. I had a sleeping bag rated for winter. But my feet were cold the entire night. Not the kind of cold that goes away in the morning. The kind that makes you wonder how long you could actually survive like this. Around 3 AM, I gave up on sleeping. Sirens screamed past. Lights from the city never turned off. My brain couldn’t shut down.
A few times during the night, people approached. Tourists curious about what we were doing. Homeless individuals asking if we had extra supplies. One man named Wayne came by. He told me his story. He’d been in the jail system, the shelter network, fighting to survive. And when I asked him what he needed, he paused and said: “It’s beautiful that people care. We’re all the same people.”
What Changed
My colleagues and I talked about it the next morning, all of us exhausted and cold. Francis Wong said it perfectly: we experienced “luxury homelessness”—we had the option to get up, go inside, and never do this again.
Real homeless individuals don’t have that exit. Annisa Saidaoui told me she’d never take her bed or a shower for granted again. Michaela Douglas said she’d start carrying snacks and hand warmers. Jennifer Draper emphasized that the authenticity of the experience mattered—it wasn’t a hotel fundraiser. It was real, and that’s what made the difference.
I personally raised $1,250 for the cause. My team at Ascential raised over $20,000. Money that went to organizations like UNICEF and Breaking Ground—groups actually working to move people from the streets into stability.
The Real Lesson
I learned that homelessness isn’t something you can solve in one night. It’s systemic.
It requires ongoing community support, policy changes, and infrastructure. But I also learned that showing up matters. Not as charity. As solidarity. As acknowledgment that these are human beings facing structural barriers, not problems to be solved from a distance.
I still think about Wayne. About his gratitude for people caring. I think about how I can stay involved—not just by donating, but by staying informed and staying present.
That’s what that cold night in Times Square taught me.