30 Years of Summer Search Boston: Meet Sarah-Simone
May 19, 2026

May 26, 2026

Meet Summer Search Alum Brian Jenney: From Uncertainty To Possibility

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Brian Jenney joined Summer Search in 2000. Like many young people, Brian didn’t step into Summer Search with a clear path laid out in front of him. In fact, he almost didn’t go at all.


When he was accepted into the program, he was shocked and then immediately overwhelmed. A three-week wilderness trip to Moab, Utah? Camping, hiking, and climbing? None of it felt like it fit his life. He had never been on a plane. He had never gone camping. At the time, he was smoking before school each day and wasn’t sure he could run the three miles the program required at the time. Moreover, he was “toying with the streets” and unsure of his overall direction in life.


So he said no. And then his mom made him say yes.


Brian’s first Summer Search trip experience was far from easy. He got sick on day one. He was pushed physically and mentally in ways he had never experienced before. But somewhere between the hikes, the kayaking, and the unfamiliar terrain, something shifted.


For the first time, he saw himself differently. Looking back, Brian can pinpoint the deeper impact of that experience in terms of what it made him believe was possible:

 

“I was toying with the streets and I was thinking, which direction am I going to go? And doing [the first summer trip] – being around kids who were not only pretty affluent, but doing this camping thing when I had zero experience – it gave me this idea like, maybe I can do all sorts of stuff? Maybe I can do whatever the heck I want. It unlocked this possibility in my brain that there’s a lot out there for me, rather than just what’s directly in front of me.


Brian’s mentors, Linda and Katherine, didn’t go easy on him. They held high expectations. No excuses. Be on time. Be prepared. Run the miles or don’t go on the trip.


That structure gave Brian something he hadn’t had before: clear guardrails and honest feedback. It taught him discipline, accountability, and how to take feedback: skills that would stick with him long after the program ended.


Summer Search also built up his confidence. Like the time he faced his fear of heights and rappelled down a cliff.  Someone snapped a photo and that experience that landed him on the cover of the annual Summer Search calendar. For a young person searching for validation, it meant everything to be seen that way.

 

I was insecure and it felt really good to have somebody look at me and say this person is a reflection of this organization.”


One of the most unexpected long-term outcomes of Brian’s Summer Search experience is the habit of running. At that time, to qualify for his summer trip he had to run three miles. That requirement forced him to quit smoking and get serious about getting in shape.
More than 26 years later, Brian is still running those same three miles, now around Lake Merritt. What started as a requirement to go on his first summer experience trip has become a lifelong practice that gives him “all sorts of time to think, reflect, and be healthy as an adult. It’s actually one of the best habits I could have ever imagined I’d pick up. And I directly owe that to Summer Search.”


Today, Brian is a software developer in the San Francisco area and runs his own coding bootcamp, combining his technical skills with his entrepreneurial spirit. But when he thinks about the future, it’s not just about success or financial stability. He wants to mentor others:


“I want to spend more of my life mentoring others, in the same way that Summer Search has done for me. I see those tiny moments where you could meet somebody that’s just a few steps ahead of you and they could give a little bit of guidance or ideas about what you can practically do.”

 

Brian Jenney Representing Clorox at the Meet Magento Conference in NYC

Brian Jenney Representing Clorox at the Meet Magento Conference in NYC

Brian advice to current Summer Searchers and young people in general: “Stay practically optimistic…look for the ways that you can improve, even incrementally, in your own life and really dig into those things.” Recognizing that the world right now, can feel scary, stay open to opportunities, to unfamiliar environments, and to people who are different from you.  He also says “don’t smoke cigarettes!”

 

Reflecting on his history with Summer Search overall, Brian shared:

 

“These kinds of moments and experiences can not only be pivotal, but they’re incredibly rare. It’s such an incredibly rare thing for somebody to pluck you out of a crowd and say ‘Hey, I’m going to change your life. I’m gonna send you somewhere that you’ve never been and you’ll do an experience that otherwise you probably wouldn’t have ever done.’ To have that kind of experience is an amazing opportunity. Don’t turn it down, and keep your mind open. Be prepared to have your mind changed.


Brian’s Summer Search story illustrates how Summer Search can catalyze transformations, not just for our individual participants, but for their families, and their wider communities. The desire to help others, even in small ways, is one that so many of our alumni share. Whether they go on to be entrepreneurs, business leaders, or to work in a nonprofit like Summer Search, when our alumni go on to make a positive difference in the world as purpose driven leaders, the impact of Summer Search ripples out far and wide.