On the bus ride to Manhattan, Shaileen Brighton-Ortiz began to fret. Would she say the wrong thing on the city streets? Would she act the wrong way? Or would she appear insensitive? even detached, if she wished someone a simple “good night”?

How do you have a good night, or sleep well? she wondered, when you are homeless? 

All that worry gave way to purpose as Shaileen and nine other Ability Beyond employees arrived in New York at 10 p.m. to offer food, clothing, toiletries, masks, hand sanitizer, and warm company to people without homes, through an initiative called Midnight Run. The volunteer effort was a chance for AB employees to unite through humanitarian action beyond the work environment, and to grow as service workers in their capacity to dignify and uplift those in need.

“Once we began handing out bags, I didn’t have the luxury of thinking about me or wanting to be perfect in my delivery,” said Shaileen, a 15-year veteran of AB who serves as assistant director of programs and services. Instead I was overcome by concern, and wanting to know more about the people we met.

The Oct. 14 run was coordinated by Breathe Equality (BE), an employee resource group for Black staff at AB which Shaileen chairs. BE formed in 2020 in light of the murder of George Floyd, to educate, lead, inspire, and engage coworkers in meaningful efforts to combat stereotypes.

As such, Midnight Run was a natural fit.

“If we believe in shaping diversity, inclusion, and equality within the organization, we also commit to shaping these values in the community,” said Dwayne Moore, a program manager who co-chairs a community outreach pillar of BE with fellow program manager Carol Drummond.

Together they spearheaded the October run, which took over a month of meticulous planning to pull off, from coordinating a crew to managing donations, collecting enough food for 200 bagged lunches, and making sandwiches by hand in a seamless assembly line at the Chappaqua office. It was an all-hands-on-deck endeavor, with leadership, management, and staff involved. All contributions came directly from generous colleagues at AB, as well, including the BE community: 52 members and 42 non-Black allies in racial justice.

“Everyone was excited to chip in, and everyone wanted to help distribute the meals,” said Carol. Dwayne shared the spreadsheet at 4 p.m., and the next day it was mostly filled in.

Then came the run itself.

“Driving into the city, I got the feeling that everyone understood the significance of this event and the impact of touching lives,” Dwayne said.

That, after all, is the higher purpose of Midnight Run,a program established in 1984, not to solve homelessness but rather to create a “human exchange” between the housed and the homeless to share understanding and affection. Each year the nonprofit coordinates over 1,000 relief missions like the one undertaken by BE.

Through Midnight Run, volunteers come to see people on the streets as real people, not a commodity, the website reads. And homeless men and women interact with mainstream adults and teenagers whose commitments and concerns go beyond their own lives and families.

By this measure, the BE trip was a true success.

“The run left me in deep thought,” said Alexis Parker, an employment specialist who came to consider her own implicit bias during the experience. “I saw so many people who looked just like me, young, black, and eager. I saw people who looked nothing like me, and at first glance I would never double back to think they were homeless. I felt equally drawn to them.

Alexis painted a vivid scene: heavy rain coming down and drenching everything, with paper bags breaking, too few umbrellas for the entire volunteer crew, and the growing realization that reusable bags were scarce. It wasn’t the smoothest sailing, she said, but it was “the most genuine” and she would participate in Midnight Run over and over again” Amy Brown, controller for AB, said she too would do it again in a heartbeat.

For Dwayne, it was the last stop of the night, on 58th street, that gave him lasting pause. Everyone has an assumption about what homelessness looks like, he said, but there, in the center of the city, he saw all types of faces.

“There were a lot of young people,” he said. “That stuck with me.”

Volunteers came away with perspective and unforgettable memories as well as questions with no easy answers. Shaileens’ big question was deceptively simple: how could this homelessness be? 

“This is the city where the ball drops at midnight on New Year’s Day, seen by millions around the world,” she said. “Yet there we were, feeding the homeless right in front of an upscale Nordstrom. I was sad, I was confused, yet I felt fulfilled, to have done something good that night. More than anything else, I was humbled.