Let me start by wishing everyone a Happy Thanksgiving! With the holiday break upon us, it feels like the perfect time to reflect on the people and roles that make boarding schools truly special. Ask anyone in a boarding school community what the hardest role is, and you’ll get all kinds of answers because every role is demanding in its own way.

Some might say the Head of School has it hardest. They’re the ones ultimately responsible for the school’s entire operation, managing finances, balancing the needs of parents, students, and teachers, and making decisions that shape the school’s future. Every major choice, every critical issue, and every bit of responsibility rests on their shoulders. It’s a high-stakes role where the pressure is constant.

Others might suggest that teachers have the toughest job. Teachers don’t just instruct; they become mentors, advisors, and coaches. They invest countless hours into lesson planning, grading, and building relationships that go beyond academics. Teachers often become like family to students, helping them realize their potential and providing support that shapes them for life.

Then there’s the Admissions Director, whose job requires not only spotting potential in students but also the stamina to travel, recruit, and make tough calls on who joins the community. Admissions isn’t just about filling seats, it’s about shaping the school’s culture and future. Admissions directors work under high pressure to build a vibrant, inclusive student body while meeting enrollment goals.

But if you ask those of us who live and work in Residential Life, many of us would say that our role is the hardest of all.

Residential Life staff do so much more than supervise dorms. We live alongside the students, becoming part of their lives in ways that only happen when you’re there day in and day out. We’re there when they wake up, when they go to bed, and every moment in between. Our job doesn’t end when classes are over; in many ways, that’s when it truly begins. We’re there in the quiet hours of the evening, when students need someone to talk to, or early in the morning when they need encouragement before a big day. We are a constant presence in their lives, offering the steady ground they can rely on.

We become their life coaches, helping them through the daily challenges of being away from home. We’re there to listen when they’re homesick, stressed, or overwhelmed. We’re often the first adults they turn to when they’re struggling, and we provide comfort and support through every high and low. In so many ways, we are like their second parents, reminding them to eat well, encouraging them to rest, and teaching them the importance of balance and self-care.

For many students, especially international ones, we’re also a bridge to a new culture and language as unofficial ESL teachers. We help them navigate not only the challenges of academic life, but also the nuances of a different world. We celebrate their cultural traditions, create a welcoming space for them to share who they are, and do everything we can to make them feel at home.

We often become mediators, stepping in to help when friendships hit rough patches or roommate conflicts arise. Living in close quarters can be challenging, and we help students learn the skills they’ll need for the rest of their lives: compromise, communication, and empathy.

And then there are the countless small, everyday logistics that keep the dorm running smoothly. We’re constantly managing schedules, keeping track of students, organizing activities, and making sure the routines that make boarding school life possible are kept on track. We plan weekend events, manage curfews, and handle the little emergencies that come up all the time. We’re always there, ready to step in when someone is sick, hurt, or just having a rough night.

The hardest part, though, may be the emotional toll. We care deeply for our students, and sometimes we’re the only ones who notice when something isn’t right. We see when a normally cheerful student becomes withdrawn or when someone is struggling in ways they may not feel comfortable sharing. We watch over them quietly, instinctively, always ready to lend support or step in to help.

We give so much of ourselves to these young people our time, our energy, our weekends, and our hearts. We do it because we believe in them, because we want to help them grow and discover who they can become. We go to great lengths to make them feel seen and supported, because we know those small acts of care make a world of difference.

Working in Residential Life isn’t just a job; it’s a commitment to showing up every day as a source of strength, compassion, and guidance. It’s about being a role model, someone they can rely on and trust. We have to maintain boundaries while being approachable, encourage independence while providing support, and teach responsibility while being understanding. We see these students through their highs and lows, helping them find resilience, independence, and a sense of self.

So, what’s the hardest position in a boarding school? Every role has its challenges, and each one is essential to the school’s success. But Residential Life staff face a unique challenge: caring for students in a way that reaches into every corner of their lives. We’re there to guide them not just as students but as young people on the journey to adulthood.

It’s exhausting, sometimes overwhelming, and it’s a role that most people don’t fully understand. But it’s also one of the most rewarding. To help these students feel valued, to watch them grow and change, and to know we played a part in that journey that’s what makes every moment worth it.

As Ernest Hemingway said, “Courage is grace under pressure.” Residential Life staff embody that grace every day, quietly guiding, encouraging, and supporting young people as they find their way forward.

P.S., I would like to thank Kenya Govan and Jermaine Gill my dorm parents when I attended boarding school!