Easing the Transition: Supporting Students as They Head Back to School

As the days grow shorter and the first signs of fall begin to appear, the shift from summer to school year is palpable for students, families, and educators alike. While some students eagerly anticipate the return of friends, routines, and opportunities for growth, others may feel a rising sense of anxiety or uncertainty. At Rock Point School, we recognize that the transition back to school is both a practical and emotional process, and that it looks different for every student.

Some students are returning to Rock Point with confidence, while others anticipate joining our school community for the first time. Wherever your student is coming from, we believe that how they experience the first few weeks of school can shape their success for the rest of the year.

Here are some ways we support students as they prepare for the school year.

Acknowledge Mixed Emotions

Returning to school often brings a wave of feelings – some expected, some surprising. Excitement, nerves, hopefulness, fear, and even grief for the end of summer freedom can coexist.

We’ve learned that students feel more ready to face these transitions when the adults around them acknowledge the complexity of their emotions. Rather than pushing students to “look on the bright side” or offering quick fixes, we recommend taking time to listen with empathy. Ask open-ended questions like, “What are you thinking about as the school year starts?” or “What are you hoping will be different this year?” Give students space to share the good and the hard. Simply knowing that their feelings are valid can relieve some of the internal pressure they may be carrying.

At Rock Point, we begin the year with intentional conversations and reflective activities during Orientation week that give students a chance to share where they are emotionally and mentally. These conversations help us meet students with compassion, and they create a learning environment that feels safe and responsive.

Gradually Reestablish Routines 

Over the summer, sleep schedules, mealtimes, and screen habits often shift. While it’s understandable to have more flexibility in the summer, returning to a daily structure can help students feel more in control and less overwhelmed when school starts.

Rather than making drastic changes overnight, start with small adjustments: going to bed and waking up a bit earlier each day, having more consistent meals, or setting aside time for reading and quiet focus. These subtle shifts can help students feel less jolted by the return to full days and academic responsibilities.

At Rock Point School, we design the opening weeks of the school year with this in mind. While we do establish a clear daily schedule, we slowly work up to full school days. Our goal is to help students gradually adjust so they can engage meaningfully in both academic and community life.

Focus on Connection

We know that students learn best when they feel known, seen, and valued. That’s why we center connection in our back-to-school approach. During the first couple of weeks of school, our staff prioritizes community building. From group reflections and goal-setting to team challenges and shared meals, we invest time in helping students feel a sense of belonging. Teachers and residential educators get to know students’ interests, strengths, and concerns before diving into academic content. We see this relationship-building not as optional, but as foundational to students' experience in school. 

Support Executive Function Skills

It’s common for students to feel rusty when it comes to managing time, materials, and responsibilities after summer break. For students who already struggle with executive function skills like organizing their work, following through on tasks, or remembering deadlines, the transition can feel especially daunting.

At Rock Point School, we teach and reinforce these skills explicitly. Staff help students create organizational systems that work for them, check in regularly to support follow-through, and offer tools like planners, visual schedules, and reminders. We emphasize the importance of these skills beyond the classroom, and remind students that they will transfer into many other settings.

Setting up simple supports at home can also be helpful. Create a designated space for school materials, a shared calendar with upcoming events, or a Sunday check-in to talk about the week ahead. 

Embrace a Fresh Start

Every school year offers students a chance to try again, to grow, and to redefine themselves. This is especially important for students who have faced academic or personal challenges in the past.

One of the gifts of being part of a small, relationship-based school like Rock Point is that students can start fresh, not just on paper, but in practice. We talk openly about what it means to learn from mistakes, take healthy risks, and show up authentically. We also ask students to reflect on who they want to be this year, not just what they want to achieve. This helps shift the focus from pressure and performance to purpose and growth.

Adults can encourage this by asking reflective questions like, “What do you want this year to feel like?” or “What would it mean to feel proud of yourself this fall?” These questions can spark meaningful conversations that set the tone for the year.

Work Together as a Team

We know that students learn best when they feel known, seen, and valued. That's why we center connection in our back-to-school approach.

Transitions can be messy, and that’s okay. What matters most is that students feel supported through the process and empowered to begin again. With patience, encouragement, and community, we can help every student start the school year feeling capable, connected, and ready to grow.