Toby’s Story: Finding His Calling After 9/11

Women’s dress shoes, covered in dust.

That is one of Toby O’Berry’s most vivid images from Sept. 11, 2001. “The amount of women’s dress shoes that were in the streets, on the sidewalks. People just ran out of their shoes.”

An investment banker for Morgan Stanley, Toby’s office was on the 56th floor of Tower Two in the World Trade Center. On that fateful morning, he was running late after staying up to watch the Giants-Broncos game the night before.

His train came to a halt one stop away from the Cortlandt Street station, which was located directly below the World Trade Center. The announcement was there had been a plane crash.

Toby walked into the atrium between the two towers and looked up to see the second plane hit. “Huge pieces of façade were raining down on people. The lady next to me froze, looking up at the explosion, so I grabbed her and we ran.”

Growing up in Iowa, Toby admired his father’s community involvement. Phil O’Berry served on the YSS Board of Directors for 34 years and was a founding board member of Iowa Homeless Youth Centers (IHYC), a YSS organization that seeks to end youth homelessness.

As a kid, Toby volunteered with his dad—riding in the IHYC street outreach van, handing out hygiene items and blankets to kids in Des Moines. “I grew up with YSS. This was like my home away from home,” he says. “But I never thought I would work in a nonprofit.”

After graduating high school, Toby earned his degree in management and economics, then went to Denver to get his MBA specializing in finance and real estate. In 2000, he moved to New York City to work at Morgan Stanley, attending night classes at NYU to become certified in investment banking. He bought a studio apartment on the upper west side and planned to make his life in New York.

Then 9/11 happened.

Like many Americans, the day had a huge impact on Toby and made him take stock of his life. After a few months, he saw how his co-workers dealt with the trauma in different ways—from drinking to extreme exercise to getting married to breaking off relationships.

“For my mental health, I realized I needed to not be in New York,” he explains. He wanted to come back to his Iowa roots and be close to his family.

In 2002, Toby returned to Des Moines and started working at Principal doing asset management. Wanting to get involved in the community, he volunteered at Orchard Place, then was asked to serve on the board.

“I was like, man—the nonprofit field is really amazing!” Toby says. He started applying to nonprofits for positions ranging from frontline worker to chief financial officer. “I didn’t care, I just wanted in. But nobody would hire me because they thought, ‘Who the heck is this guy with a master’s degree in finance and real estate?’”

Finally, YSS founder and then-CEO George Belitsos told him about one opening at IHYC: an entry-level administrative position. Toby said “yes” immediately.

Toby started at IHYC answering phones; six months later, he was rebidding the organization’s contracts. His title changed from Administrative Assistant to Office Manager to Director of Operations—with no pay raise, which was fine with him. “I just loved learning about YSS and all the services we provide in our community,” he explains.

When the IHYC Director resigned, Toby was invited to apply for the position. He interviewed and got the job. “And I haven’t looked back,” he says.

Today, Toby serves as the Director of IHYC and Associate Vice President of Transition Services for all of YSS, helping young adults who are experiencing homelessness to transition into safe, secure housing. He is overseeing major projects such as IHYC’s Rooftop Gardens, which will provide opportunities for homeless youth to gain work experience and access healthy foods.

Although Phil passed away six months before Toby started at IHYC, Toby says his father “would be so proud” knowing his son works at the same organization he helped establish decades ago. Above Toby’s desk is a framed photo of his father and his hand-written application to serve on the IHYC board in 1985.

“It’s fun to remember him and to work at the same place I grew up volunteering,” Toby explains.

In December 2019, Toby and his family returned to New York to visit the National 9/11 Memorial. They went on a guided tour before the museum opened, which allowed them to view the exhibits in private. Seeing the footprint of the towers and the memorial of those who died was a somber experience.

Toby still struggles with survivor’s guilt, saying it’s difficult to acknowledge how fortunate he was without minimizing his trauma.

“My experience was so different from the individuals who were in the building and had to walk down the stairs, or the first responders who were the heroes that day,” he explains. “My trauma was more visual, seeing a lot of things from the outside. It was a traumatic event and affected me significantly. But, it was not as hard as what lots of other people went through.”

Toby’s main takeaway from his experience is that it led him to YSS and IHYC. It made him want to give back to the community.

“If I hadn’t experienced 9/11, I don’t think I would be in this spot,” he says. “I’m so happy to be at YSS. This is what I love to do. It’s my forever home—it’s exactly where I want to be.”