Greg B. didn’t sign up for Simpson Housing Services’ youth mentor program on a whim. And he certainly didn’t come back for a second year out of obligation. He came back because the first year worked—because the relationships mattered, because the structure made sense, and because the experience felt like time well spent.
“I want to use my time productively,” Greg says simply. After decades of professional life focused on systems, data, and process improvement, he reached a season where work was slowing down, his children were grown, and he felt ready to re-engage in a way that was more personal. When he saw a flyer about Simpson’s mentoring program, it landed at exactly the right moment.
Greg was no stranger to Simpson Housing Services. His connection goes back to the early 1990s, when he first became involved through his workplace and later served on the board. Over the years, he volunteered in various ways, including overnight shifts at the shelter. Life eventually pulled him in other directions, but Simpson never left his orbit. So when the mentorship program caught his attention, it felt less like discovering something new and more like returning to something meaningful.
What ultimately brought him back for a second year, though, was confidence—in the program itself.
“So many programs say they have goals, but the way they’re structured doesn’t actually support those goals,” Greg explains. “This one does.”
Rather than relying on a traditional one-to-one mentoring model, Simpson’s program, (open to ages 12-18) brings together small groups of youth—typically ages 14 to 16—with multiple adult mentors. The combination of peer connection, consistent adult presence, and strong safety boundaries is intentional.
Greg admits the structure surprised him at first. Like many people, he assumed mentoring meant one adult, one child, and a series of activities. But he quickly came to appreciate the group model—not just for the kids, but for the mentors too.
“It’s less intimidating,” he says. “You’re not on your own. There’s support built in for everyone.”
That structure also meant slowing down. As someone wired to optimize systems, Greg sometimes wanted more time, more activities, more opportunities to deepen relationships quickly. Program leaders helped him understand why pacing, consistency, and safety mattered just as much as enthusiasm.
And then, something happened that confirmed he was exactly where he was supposed to be.
One evening, during a regular mentoring session, a young person in Greg’s group shared something personal—something vulnerable. It wasn’t dramatic. It wasn’t rehearsed. It was simply honest. A question, or a story, that you don’t offer unless you trust the people in the room.
“That moment,” Greg says, “was the checkmark. That was the moment I knew—this is why I’m here.”
For Greg, those moments of vulnerability are everything. They signal that a relationship is forming. That a young person feels safe enough to open up. And perhaps most surprising to him was how willing these teenagers were to engage at all.
“Most teens aren’t exactly lining up to talk to adults,” he laughs. “But these kids? They’re open. They want connection. They want some fun. They want a break from the weight they carry.”
What Greg sees in these youth is resilience—the kind you don’t fully understand until you spend time with it. Supporting the joy, creativity, and wisdom of a young person, and seeing their humor, curiosity, and determination shine through is what the program is all about.
When asked what makes a good mentor, Greg doesn’t point to credentials or personality types. Instead, he talks about willingness: the willingness to show up, to listen more than talk, to bring a little fun energy, and to hold boundaries when needed. Most importantly, he emphasizes commitment.
“This isn’t something you dip your toe into,” he says. ““If you’re in, be in and be present. The kids really benefit from having consistent, caring adults in their lives.”
The time commitment, he adds, is manageable—about three hours one evening a week during the school year, plus a bit of training and the occasional field trip. What it gives back, though, far outweighs the hours.
Greg’s advice to anyone on the fence is direct: think it through, and if you can commit, do it.
“You go in thinking you’re going to give these kids something,” he says. “And what’s going to happen is—you’re probably going to get more than you give.”
Click here to learn more or sign up to become a Mentor.
For questions, contact Jocelyn via email here.