For Esther Despage, the Boys and Girls Clubs of Boston (BGCB) wasn’t just a place to go after school. It was also the backyard of her life. Growing up literally across the street from the Berkshire Partners Blue Hill Boys and Girls Club, Esther started her journey at eight years old and stayed until the day she graduated high school.
“The Club introduced me to everything,” Esther recalls. “Community, lifelong friends, and relationships with staff that felt like family. We watched each other grow up.”
Her time at the Club was a whirlwind of exploration. She was a member of the dance team, a junior counselor, and even a champion golfer. Esther won a nine-hole tournament after sinking a high-pressure hole-in-one on a downhill slope.
But it wasn’t just about sports and trophies. It was about the moments of encouragement that stuck with her for life. Esther shared a memory of Celtics player Delonte West pulling her aside during a clinic at the Club.
“He said he could see I was holding back,” she remembers. “That I was nervous because I was the only girl. And he told me: you have what it takes. Don’t be afraid to put your best foot forward.”
Leadership at the Club was not a title. It was something you practiced. In her early teens, Esther joined the Young Leaders program, a pathway that helped members build confidence by stepping into real responsibility. She shadowed counselors, worked with younger kids, and eventually became a junior counselor herself. The staff saw something in her before she had a name for it.
“As a kid, you’re not thinking about leadership positions. But when they see how you move, they open that door for you. It gave me the confidence to put myself out there and keep asking, how can I be better?”
After high school, Esther took that confidence to the University of Connecticut, where she studied biology and walked on to the Division I women’s basketball team as a freshman with no scholarship and no guarantee.
“It was the toughest thing I’ve ever done, physically and mentally,” she says. “It taught me discipline. I’d be at conditioning, run across campus for an 8:00 AM class, and be back for scrimmages by 2:00 PM.”
After she graduated, she discovered that life rarely moves in a straight line.
She began her career in healthcare and was building toward graduate school. Then the pandemic hit. She was laid off, and the plan she had been carefully preparing for suddenly felt uncertain.
It was one of those moments that forces honesty. Not just “what can I do next,” but “what do I actually want.”
Like so many people, she had to ask herself a hard question: Do I go back or do I pivot? Esther chose to pivot. And she chose cybersecurity, an industry far from what she studied.
“Totally different,” she says. “But there were so many skills that I wasn’t using that I could apply. And because the industry is growing so quickly, there are so many things that I can get into.”
Esther knew she had the drive, but she needed a roadmap. That’s when she reconnected with her Club roots through CareerLabs.
Esther’s reconnection with BGCB began with a simple invitation. A friend from her Blue Hill Club alumni circle let her know about a financial literacy event in partnership with Fidelity. Esther went. It was the first CareerLabs event of the year, and it introduced her to something she did not realize she had been looking for.
Launched in 2025, CareerLabs is an initiative that supports BGCB alumni in building meaningful job and career pathways through coaching, mentorship, and resources. Through monthly networking nights and one-on-one support, CareerLabs helps alumni explore what’s next, strengthen their professional presence, and connect with people who can help them move forward.
Esther kept showing up. First Thursdays networking events. Alumni connections. Conversations with professionals across industries. A growing sense that she did not have to figure out the next chapter alone.
“I used to be someone who was like, no, I can do it myself,” she says. “But you don’t have to do it by yourself. The help is there.”
CareerLabs helped Esther strengthen her resume, LinkedIn profile, and cover letters. More importantly, it connected her to people who could help her understand the cybersecurity landscape, talk through roles, and get more clarity about what she is aiming for.
“CareerLabs is a great vehicle for getting you from point A to point B,” she says. “And it’s not linear. It’s not just one way. There are a bunch of different paths that I can go down to explore what works best for me.”
That matters because career change is rarely a direct path. It is learning, adjusting, meeting the right people, and building confidence as you go.
Today, Esther is working in technology while actively applying for roles in cybersecurity. She is doing the work. But she is not doing it alone.
When Esther talks about why she stays involved, it comes back to something simple: the Club is not a chapter you close. It is part of who you become, and it is a community you can return to when you are ready for your next step.
Are you a Club alum looking to make your next big move? Whether you’re pivoting careers like Esther or just starting out, CareerLabs is here to help you navigate your journey. Reach out to see how we can help you build your own bridge to the future.
