Easing the Transition: A Guide to Starting the School Year

Meagan Ledendecker • August 4, 2025

As summer winds down and the school year approaches, our children often experience a mix of emotions from excitement and curiosity to worry and anxiety. Whether your child is returning to familiar routines or stepping into something entirely new, transitions can be challenging for both children and parents.

 

The good news? With a little forethought and gentle structure, the shift from summer to school can become an opportunity for growth, connection, and calm. The Montessori philosophy reminds us that preparing the environment is key, and that includes preparing our home routines, emotional landscape, and mindset for the change ahead.

 

Reestablishing Routines

 

One of the most effective ways to support a smooth transition is to gradually reintroduce routines. Children thrive on consistency and predictability, and reestablishing a gentle rhythm can reduce stress and help everyone feel more grounded.

 

Sleep Schedules

 

The shift from late summer nights to early school mornings is often the trickiest. Rather than expecting a sudden adjustment on the first day, we recommend starting 10 to 14 days in advance. Gradually move bedtimes and wake-up times earlier in 15-minute increments. The goal is for your child to wake feeling rested and ready when the school year begins. Pair this adjustment with a calming, age-appropriate bedtime routine to support both physical rest and emotional regulation.

 

Morning Routines

 

A consistent and peaceful morning routine can transform the start of the day for the entire family. With a few subtle adjustments, we can also encourage our children to participate in preparing for the day ahead. For example, offer two outfit options for younger children, or encourage older children to choose and lay out their clothes the night before. A visual checklist with steps like getting dressed, eating breakfast, brushing teeth, and packing up can help alleviate the pressure. For added fun and independence, laminate the visual guide and let your child check off each task with a dry-erase marker. Ultimately, it helps practice the morning routine together before school starts, so it feels familiar and low-pressure.

 

Preparing Lunches and Snacks

 

Involving children in packing their own lunch fosters independence and gives them a sense of responsibility. Set up a small shelf or refrigerator section with healthy, ready-to-grab options. With a little support, even very young children can help pack their snacks and lunches the night before or as part of the morning routine.

 

Creating Calm and Order at Home

 

Designating a special area for school items helps build a sense of order and capability. Low hooks for backpacks, a bin for shoes, and a tidy shelf for lunch bags or outerwear give your child the tools they need to manage their belongings independently.You can even “practice” coming home before the first day of school. Having your child hang up their backpack, unpack their lunch, and put things away helps establish habits that will carry through the year.

 

Supporting Emotions

 

It’s completely normal for children (and us!) to feel a mix of emotions about returning to school, especially when starting somewhere new. The key is to remain open, curious, and validating.

 

Encourage open conversations about feelings that might be arising. Instead of trying to fix discomfort, try reflective listening: “It sounds like you’re feeling a little nervous about meeting new friends.” We can also model a positive mindset by highlighting joyful aspects of school, such as reconnecting with friends, engaging in favorite activities, or exploring something new.

 

Another approach is to create rituals to mark the transition, such as an end-of-summer breakfast, a special note tucked into a lunchbox, or a celebration to mark the start of the school year.

 

Cultivating Connection

 

Transitions are smoother when children feel supported and connected to their community. If possible, visit the school before the first day, especially if your child is starting something new. Even a walk around the outside of the building can provide helpful familiarity. Coordinating playdates or meetups with classmates can help build or rebuild social bonds. If your child is interested, it can also be fun to explore extracurricular activities that foster a sense of belonging.

 

Maintaining Wellness and Balance

 

We do better when we feel better. To help children sustain their energy for the school day, focus on nutritious meals, especially a healthy breakfast that will fuel concentration and energy. To support a healthy balance between screen time, movement, and rest, work with your child to establish technology boundaries and screen limits before the school year starts. This helps children adjust ahead of time to different (and hopefully healthier) habits.

 

Encouraging Independence and Collaboration

 

Back-to-school doesn’t have to be something adults “do to” children. When we invite children into the process with genuine collaboration, they begin to feel more in control and more confident. From setting up routines, to preparing meals, to expressing their feelings, children are capable of contributing meaningfully to the process.

 

The result? A smoother transition, a greater sense of peace, and children who feel ready to step confidently into the school year ahead.

 

Curious to learn more about supporting children in developing habits that serve them for a lifetime? Visit our school today!

By Meagan Ledendecker February 23, 2026
One of the quieter, less visible practices in a Montessori elementary classroom is the Child-Guide conference. You may never see it listed on a schedule or mentioned in a weekly update, yet it plays a profound role in children’s experience at school. Relationship Comes First The primary purpose of these conferences is to establish, maintain, and strengthen the relationship between the adult and each child. This focus shifts the dynamic from a teacher looking for faults or scolding about unfinished work. Rather, it’s a collegial conversation that enables children to take an active and engaged role in their own education. These connective conversations are grounded in relationship-building because when children feel emotionally safe and genuinely respected, they are far more willing to reflect, stretch themselves, and take responsibility for their growth. Every Child, as Often as They Need Montessori Guides aim to meet regularly with every child, but what “regularly” looks like can vary based on individual needs. Some children benefit from a longer, more formal conference every few weeks. Others need brief, frequent check-ins, sometimes lasting only a minute or two. These short moments might look like a quick conversation at the beginning of the morning, a gentle pause beside a table, or a quiet walk across the room together. The length of the meeting is not what matters. What is important is the message it sends: “I see you. I know your work. I care about how this is going for you.” What Happens in a Child-Guide Conference? While conferences vary based on each individual and the moment, they often include: The child bringing their learning journal or work (finished and unfinished) The guide bringing observational records A shared look at what has been accomplished Gentle reflection on what still feels unfinished Planning for what might come next Scheduling new lessons or presentations Support with larger projects: breaking them into steps, mapping timelines, imagining the finished product This collaborative time also provides an opportunity to experiment with new strategies (“Would you like to try creating a prioritized list?”), celebrate successes (“You worked so hard on your presentation! How did it feel to share your work?”), and reflect upon challenges (“It seems like you’ve been feeling a bit stuck in your research project. Tell me more about what is going on.”). Learning to Define “Finished” One of the most freeing lessons children learn in Montessori is that not every piece of work must be finished to an adult’s standard. Sometimes children accomplish exactly what they set out to do, and continuing would add nothing meaningful. Other times, interest has naturally ended, and letting go is healthy. This is not about lowering expectations. It is about honoring children’s internal sense of completion and learning when to release what no longer serves a purpose. Trusting Children’s Self-Assessment A cornerstone of these conferences is trust. Guides listen carefully to how children assess their own work and articulate their goals. When an adult truly accepts children’s self-assessment, something powerful happens: children begin to see themselves as capable, thoughtful, and worthy of being taken seriously. Children often receive more from the tone and sentiment of these meetings than from the actual content discussed. The Whole Child Matters Because Montessori education is concerned with the whole child, conferences may naturally move beyond academics. A Guide might gently offer support with social dynamics or ask about recent struggles during outdoor time. These moments provide a safe space for children to reflect on their own social, emotional, and physical development, and to recognize that there is a network of support. When Relationships Need Repair Even in the most thoughtful classrooms, relationships can become strained. What matters is how adults respond. It is never too late for a Guide to sit with a child and say, honestly: “I’ve been thinking about how we’ve been interacting recently, and I’d love to brainstorm with you about what I could do differently.” When an adult takes responsibility, without demanding the child do the same, something shifts. Trust begins to rebuild. Real dialogue becomes possible. Children learn from this modeling. In time, after they feel safe, they often step forward to take responsibility themselves. What Children Are Really Learning Through these quiet, intentional meetings, children learn that:  their thoughts and feelings matter, adults can be trusted, mistakes are part of growth, reflection leads to independence, and relationships can be repaired. And while these conferences may happen quietly in a corner of the classroom, their impact echoes far beyond it. This is true preparation for life. To learn more about the long-term benefits of Montessori, visit us here in Lenox, MA!
Image of a preschool aged student sitting on the floor with a moveable alphabet
By Meagan Ledendecker February 16, 2026
Explore how Montessori children learn to write through sound work, movable alphabet exploration, and a joyful, developmentally prepared process.
Image of two parents with two children hugging their children after school
By Meagan Ledendecker February 9, 2026
Learn why children need quiet decompression after school and how a “quiet landing” supports regulation, connection, and meaningful conversation.
Image of three elementary students sitting at a table with red equivalence shapes set in green frame
By Meagan Ledendecker February 2, 2026
Discover how Montessori geometry introduces equivalence through hands-on exploration, helping children build deep understanding of area, fractions, and mathematical reasoning.
Image of three elementary students holding a triangle of rope between them
By Meagan Ledendecker January 26, 2026
Explore the Montessori story of geometry’s origins, from ancient Egyptian rope-stretchers to modern classrooms, inspiring children’s wonder and curiosity.
By Meagan Ledendecker January 19, 2026
A Montessori approach to understanding disrespect: why children use strong words, how adults can stay calm, and ways to protect connection over conflict.
Show More