September 26, 2025

By Amy Jolly, Head of School

As Head of School, one of my greatest privileges is teaching a 9th grade seminar on Leadership. Over the course of the year, students reflect on their strengths, confront their challenges, set ambitious goals, and grow into leaders. By placing them at the table where decisions are made, we help them see themselves not only as students, but also as stakeholders in Applewild’s culture and caretakers of its future. It’s a formative experience that sets the tone for the confidence we aim to build in every Applewild graduate. 

As a junior boarding school, we understand the powerful immersive learning environment we offer our students. They live, learn, and lead together - they take on roles as dorm prefects, team captains, club leaders, student councilors, and admissions ambassadors. Each of these opportunities, formal and informal, gives them the chance to practice leadership in meaningful ways, repeatedly - this process builds measurable competence, and with competence comes confidence.  

Of course, confidence is not solely built on success. At Applewild, we believe that setbacks are just as valuable as victories. Whether it’s losing a tough game, struggling through a class project, stumbling during a speech rehearsal, or navigating the ups and downs of friendships, these moments teach resilience. Our students learn that mistakes are not the end of the story, nor do they define them; rather, they are necessary stepping stones toward growth. By normalizing setbacks as part of the learning process, we help students develop the grit and determination to face challenges with courage, and to try again. True confidence - and growth - comes from knowing that you can recover, adapt, and improve. 

The culmination of this growth is on full display during our Eleanor Crow Public Speaking Contest. Our oldest students write and memorize a 3-5 minute speech on a topic meaningful to them, and then deliver it in our 350-seat theater before peers, families, faculty, and a guest panel of five distinguished judges. We invite executives, politicians, entrepreneurs, and other leaders from the outside to serve as judges - they provide rigorous feedback, giving students a professional-level challenge that few their age ever encounter. While stakes feel high, every student completes this requirement for graduation and emerges more poised, confident, and empowered to use their voice to make an impact. 

Taken together, these experiences shape Applewild graduates into confident, resilient young people ready for the next stage of their journey. Each year, I have the privilege of standing on stage and offering a personalized reflection on each of our graduating 9th grade students. In that moment, as our eyes meet, there’s a shared recognition of how far they’ve come - their growth, their accomplishments, and their readiness for what lies ahead. The confidence they carry forward is not accidental; it’s the result of intentional opportunities, careful guidance, and a community that believes in their potential. At Applewild, we know that confidence comes from competence, and competence is built through the rich blend of challenges, opportunities, and support that defines the junior-boarding experience.