From Stranger to Mentor: A Conversation with Darren Chung on CASL’s Big Brothers Big Sisters Program

At CASL, mentorship is at the heart of how the organization invests in youth and community development. Through its partnership with Big Brothers Big Sisters, CASL connects professionals with high school students for long-term mentorship relationships that provide academic, personal, and emotional support.

We spoke with Darren Chung, SVP and Head of Retail Banking at Wintrust Financial Corp and member of CASL’s Associate Board, about his experience as a mentor—and the student journey that stayed with him.

Why did you choose to support CASL?

CASL really aligns with what I value. When I was looking for an organization to join and support, I wanted it to align with the same values I hold personally—similar to how I think about my own employer. CASL’s work across children, families, and seniors reinvests in the community and in quality education for all. I truly believe CASL makes a huge impact.

Is there a particular CASL program that resonates with you most?

It might be a little biased, but I helped bring the mentorship program to fruition. We launched CASL’s partnership with Big Brothers Big Sisters about three or four years ago. I’ve been a mentor ever since, and I think it’s extremely rewarding. So the mentorship program, for sure.

For those unfamiliar with it, how would you describe the CASL–BBBS program?

In short, it’s a mentoring program to help high school students have a successful future. It’s really about being a friend and mentor—supporting them with questions about academics, social situations, or simply navigating everyday life.

What has your personal experience in the program been like?

It’s been fun and rewarding. You get to do different activities and field trips sponsored by Big Brothers Big Sisters, and you build real bonds—not just with your “little,” but also with the other mentors and students in the program. It really does feel like one big family.

Can you tell us about your mentee?

I was matched with Jason for a little over three years. I genuinely looked forward to every session with him. Hearing how he was implementing strategies we worked on together and watching him grow as a student and as a young man—that was the real reward.

He ended up earning a full ride to Stanford, where he’s now studying computer engineering. That says everything.

What would you say is the most impactful part of the experience?

Just being a positive influence on someone’s life. At first, littles can be a little reserved—you’re a stranger to them. But once you form that relationship, they open up, and that’s when real mentorship begins.

They start asking about your own experiences at their age, how you navigated challenges. By the end, everyone—bigs and littles—is grateful just to have been part of it.

Was there anything that surprised you about being a mentor?

 No big curveballs. The early challenge is just getting your little to open up, which takes time. But Big Brothers Big Sisters does a great job with programming—getting everyone engaged, getting everyone out of their shell, and supporting all the matches in the program.

Did you have mentors who shaped you when you were younger?

Outside of my parents, I’d point to my swim coach and my academic advisor. Both of them created space for me to bring my questions and problems and just be a sounding board—helping me work through things by voicing them out loud.

It was also helpful to have someone outside of family, because sometimes there are things you’re more comfortable exploring with someone a step removed. Just having that person there made a real difference.

What would you say to someone considering becoming a mentor?

Do it. Being there for someone who needs it—as a friend, as a guide—is one of the most rewarding things you can do. You get more out of it than you expect.