BOXERWOOD RISING: Meet Jake Osella, land surveyor

Throughout our 25th year, we’ll be sharing stories of young people whose Boxerwood experiences shaped their passions and vocations. Have a young friend to recommend? Contact Catherine Epstein: catherine@boxerwood.org

This past November, when Jake Osella was surveying the border between our Woodland Garden and the golf course, he found himself in an unexpectedly familiar position. “There was a Boxerwood kids’ program going on,” he explained. “They were walking through, so I was telling my coworker about all my memories.”

As it turns out, this wasn’t the first time Jake had been working at Boxerwood when a troupe of lively children ambled by. Years ago, Jake connected with Boxerwood as a teen to complete some community service. He started out doing manual labor like weed-eating, but one day, “I was working in the area of one of the kids’ camps, and they were outside making lemon balm tea, like sun tea,” he remembered. “They were talking to me and wondering what I was doing, so I was just interacting and laughing with them.” Camp educator Hannah West – now Operations Director – noticed how good Jake was with kids. She asked him if he’d like to complete more of his community service working with children, and this rest is history.

“We went to the frog pond where they look for critters, and Hannah also had me hiding the golden acorns for the [preschool] story where they use the puppets…it was a blast.” He also remembers the unique responses of 3- and 4-year-olds seeing Boxerwood for the first time: “They were just blown away when they got there. Looking at the trees, looking at the flowers, they were just like ‘Whoa! Wow!’ That was a really special memory.”

He went on, “It was really good to just see them without a care in the world. The younger the kids were, the more they immediately became a team. Like maybe two kids that wouldn’t normally talk to each other, when they went to Boxerwood, it was just nothing but love. They were just so happy to be there.”

In all of these activities, Jake said, “I felt like I could play. I wasn’t thinking I was the adult in the situation. It was more like having fun with them. Running around with them, doing the crafts that they were doing. It was a really good time.” 

In fact, the experience wound up being much more valuable to Jake than simply completing his required hours. “I ended up volunteering way more than I needed for my community service because it was so fun,” he said. “It just felt like home. It felt like family. Everybody was awesome.”

Jake said that this feeling of home was especially cultivated by the people who supported him at Boxerwood. “I grew up feeling like I never really fit in, so meeting other people who loved nature as much as I did meant a lot. And I didn’t get out much. I didn’t do many camps, I didn’t play sports growing up. So that was extra special too.” Along with Hannah’s mentoring, Early Education Coordinator Jess Sullivan also played a significant role in Jake’s experience. “She kind of took me under her wing, like a very strong mother figure. I really enjoyed talking with her.” In her memories of that time with Jake, Jess recalls, “He was amazing with the kids! They just loved him. He was open to them and would take on any role I threw at him.” 

Everyone at Boxerwood, Jake said, was “very accepting of me…They were just very open arms, come on board, and they saw the potential of me being good with kids and a good teacher. I was really grateful for that…And going from doing the weed-eating in 90-degree weather to playing with kids was huge. It didn’t feel like work. It felt fun.”

After graduating from Rockbridge Community High School in 2015, Jake has continued to pursue employment that doesn’t feel quite like work. “What drew me to Boxerwood is the same thing that drew me to my current job,” he explained. “The adventure, being outside…I’m outside every single day of work for the most part. I love nature, I love trees, I love anything that grows. I feel more at home in nature than indoors.” 

Today Jake works for Perkins & Orrison, an engineering and surveying firm based in Lexington. He found the work after applying to several jobs, but he originally had no idea what land surveying was. “It ended up being a perfect fit,” he said. “After a year of working there, I felt like I understood what land surveying was. The training process takes a while, because there is so much to learn and it can be hard to teach because it requires decision-making from moment to moment.”

His official title is “Party Chief,” meaning that he’s in charge of a field crew. Projects include everything from establishing a property line to creating topographic surveys that note ground contours as well as hardscapes and trees. The work is varied, and Jake doesn’t always know exactly what he’ll be assigned to do each day. “Sometimes it’s a complete surprise,” he explained. “I love that.” 

Along with Rockbridge County, Jake has done surveying work in West Virginia, at Virginia Tech, and elsewhere. He also gets special access to places that are restricted to normal pedestrians. “I’ve gone up to Moore’s Creek Dam out in Kerr’s Creek, and you can’t access it if all the gates are locked,” he said. “So you get amazing views all over the county, and parts of the county that you would never see being a resident. Sometimes it feels like I’m getting paid to hike.”

Reflecting on the similarities between Boxerwood and his current work, Jake said, “Being at Boxerwood when I was younger, and even when I volunteered in high school, it felt very adventurous, like one thing will pull me to another. I’ll be admiring a tree, and then I’ll be creating scenarios in my imagination of history.” He went on, “it’s kind of the same thing in my job currently. If you’re doing a big survey in the woods and the mountains, it feels like an adventure. You’re looking for treasure in a way, looking for property corners from the 1800s. Sometimes you have really old legal descriptions that call for a stone or a stump that was 10 inches wide in 1895. You know you’re not going to find that, but you have to hunt for evidence that might look like a property line, or an old fence line.” 

These days, Jake spends time not just imagining the past, but also contemplating the present and the future. Considering Boxerwood, he notes, “It’s very important to preserve places like that, because the amount of open land that hasn’t been developed is dying every day.” 

His own experiences at Boxerwood also shape what he finds so singular about this place and its mission. “I remember it as being this massive place when I was little. Like an enchanted forest or something…I think it’s really important, especially in 2026, for kids to be able to have places like that they can go. We’re so digitally motivated and everyone has a screen.” 

On the other hand, he says, “that’s the real world. Boxerwood is the real world.”