After more than 25 years, The Island School alumni community has grown into a vibrant network of more than 3,300 individuals from our Semester, Summer Term, and Deep Creek Middle School programs. Our alumni span the globe, working as researchers, educators, students, entrepreneurs, and more. With such a diverse and accomplished group, there’s incredible potential to learn from one another. One of the best ways to tap into that potential is through our alumni mentoring program, hosted on The Island School Alumni Network.

Whether you’re a recent Island School graduate or well into your career, mentoring can be a meaningful way to connect, share, and grow. As an alum, you can sign up to be a mentor, a mentee, or both, depending on what stage of life you’re in and what you’re looking for.

Two Semester alumni who recently participated in the mentoring program are Kate DeWitt S01 and Jack Kenney S19. Kate and Jack connected when he was about to graduate college and Kate was able to provide some insights as he was entering the workforce. Kate reflected, “I became an Island School alumni mentor as a way to get back involved after many years watching from afar. I was an early years student, so I (hope!) that I can share some of the lessons I have learned over the course of my career, which has not always been entirely linear. It’s the twists and turns that have made it interesting, and it’s exactly that sentiment that I enjoyed sharing with Jack when he got in touch as he was about to graduate college. Be disciplined about finding, following, and continuing to hone your interests, even if it’s the untraditional thing to do! What I actually learned through speaking with Jack was that IS students are perhaps already pre-determined to seek out that passion and lead others to those pursuits as well. Our conversation motivated me to continue to challenge my own direction and areas of focus. Mentoring also re-engaged me with IS and I’ve stayed involved as a result. Definitely encourage others to give it a try, on both mentor and mentee side, as you’ll learn and be inspired, which is at the core of IS.”

What does mentoring look like?

Mentorship through The Island School can take many forms. Here are just a few examples through the lens of becoming a mentor:

• You’re an alum with years of professional experience, ready to pass along wisdom to a younger Island Schooler navigating their first job.
• You’re a DCMS graduate who attended boarding school and want to support younger students preparing for the same transition.
• You know the transition home after a Semester or Summer Term can be difficult and want to help others adjust to life back home after their Island School experience.
• You’ve faced a challenging job market and can offer guidance on what hiring managers are really looking for.

Reflecting on his own experience as a mentee, Jack shares, “The Island School network as a whole feels like an ocean of opportunity—filled with intelligent, energizing individuals who leave younger graduates like myself eager to learn and connect. In my experience, the mentorship program has been an organic way to learn and build meaningful relationships with alumni who are a bit further along in their life and career journeys. Our conversations have been impactful and grounding—their guidance and support have helped me walk more sure-footed as I begin to shape my own career identity. Asking for help is something I’m still learning to get better at, but the alumni network makes that process feel easy. I’m looking forward to meeting more Island School grads as the community continues to grow.”

Who makes a good mentee?

As an Island School alum, you are already curious about the world. To be a good mentee, take that curiosity and be willing to learn from folks who have been in your shoes before. Some examples include:

• You’re about to graduate from college or enter the workforce, but you’re nervous about the transition from schooling to a career
• You just returned home from your semester or summer term and need some guidance on how to apply all the things you learned to your life back home
• You’re looking to make a career transition, and you don’t know where to start

Ready to get involved?

Visit The Island School Alumni Network to sign up as a mentor or mentee and start building meaningful connections within our alumni community today!