Tue, September 9, 2025

Settling into September

By Barbara H Scott, Executive Director, Parents League of New York

Is it really September? Each year, I find myself asking why September is the best month of summer.  Don’t you agree? I mean, in September the sun shines often, rain visits only occasionally, and the temperature is neither too hot nor too cold. Of course, as a life-long educator, September is my happy month, not just because the weather is glorious, but because the sights and sounds of children en route to school remind me to seek new opportunities, outlooks, and growth.

Like many families, our September begins in August, given my youngest child’s rhythm as an emerging adult and college student. This also means our family’s summer begins in early May rather than late June. And, although we no longer shop for themed backpacks in July or rush to sign up for group afterschool classes with classmates, talk of school permeates our household right up until move-in day. The excitement of engaging with new teachers and ideas, connecting with valued friends, along with making new ones, does not seem to change whether a child is starting preschool or returning to college. The hopeful energy and the promise of new adventures crest like a wave on the late-summer beach.

By Labor Day, the household is quieter and cleaner. Even if that’s only during the school day. It is a relief in many ways. It is a parent’s time to recharge and get set, or reset, as the case may be. In our home, it is time for my spouse and me to determine new patterns in a mostly empty nest. So, as I settle into the season, I am thinking about the families and their kiddos starting school for the first time, particularly the milestone moment of beginning kindergarten.

I started kindergarten three times. As a mom, that is, and with three very different kids. In fact, I vividly recall the start of my eldest child’s kindergarten year. It was a Wednesday morning with the sun gently warming my shoulders. We strolled down a double-width avenue where the leaves on the trees were crisp and yellowing. Soon, we turned onto a block with handsome townhomes and an apartment building. The schoolhouse door sat midblock, on the north side of the street, and there were children and parents everywhere. 

The whole scene was a little overwhelming. Parents nervously smiling at their kids, teachers kindly but feverishly checking student lists, and my generally even-tempered and happy four-year-old gripping my hand more tightly than usual. As a new kindergarten family, we were eventually ushered into the auditorium. The principal greeted the group with a firm kindness, and after that, I remember a long line of blue colored painter’s tape.

This spot, we were told, outside the auditorium and adjacent to the schoolhouse door, was where we were meant to say goodbye to our children. Every day. No hugging at the classroom door or glancing at schoolroom materials or bulletin boards along the way. That would have to wait until back-to-school night, which was six whole weeks away! Say “goodbye quickly and quietly,” the principal clearly stated, and “pick-up is in the yard.” My heart sank. “Yard,” I muttered to myself, “isn’t that for prisoners?” Could the school principal really be referring to my impossibly darling, if a bit messy, little boy?

So, how did I manage to settle in that September? It was a process, for sure. It is easy to be swept up in a wave of calendaring activities, meal planning, and selecting bedtime books, but if I have learned anything over 30 years of parenting and being in schools, it’s that kids play the tune of their parents. If we are anxious, they may be as well. If we are happy, so may they be. And, if we are listening, they will show us the way. In a sense, the month of September, a time of familiar routine, but also unseen change, reminds me to be neither hot nor cold, to laugh when rain comes, and to embrace the newness of each stage of parenting (and life) as best I can.

Whether your child is excited about school on the first or the 100th day, as is often celebrated in classrooms everywhere, see it as an opportunity to learn something about your child and yourself. In my case, some afternoons I left my younger son sleeping in his stroller at a neighbor’s house so I could pick my eldest from “the yard.” It made the difference for him and for me. It was  part of settling into kindergarten together. I was able to see the world anew through his eyes, if only for the 15-minute walk home up the avenue. My eldest was deeply curious but also struggled with being the youngest in his class. He was playful and kind, but when following classroom schedules, he was a little slow to transition. And, my darling boy did not like the bathrooms at school. As parents, we were listening and learning. We ultimately selected a new school for our son, and he repeated kindergarten the following year. This new setting was more aligned with all of our needs, affording our son the opportunity to be in the just-right middle of the class in terms of age, among other things.

With my youngest child, school pick-ups were filled with tears. So many tears, in fact, that I often wondered what I had done wrong this third time around. Was it the school? Me? My kid? I arrived early to pick up often, brought comforting afterschool snacks, and hosted classmates for playdates, but still there were tears. My daughter was teaching me something along the way, of course, just as her brothers had before her. I needed to be more present, patient, and resourceful in ways I had yet to imagine. She required, and still does, different parts of me. Those first and 100th day kindergarten tears taught me to navigate life’s unexpected storms differently. Today I can dance in the rain more easily, knowing the clouds will eventually dissolve away.

What does this all really mean? Well, as a self-acknowledged serious person, I have learned to tap more deeply into my warmer capacities, for my daughter taught me that her deep empathy is a part of who I am, too. My middle son taught me to be more patient. His younger years were filled with energy and verve, though in adolescence, his developing brain ran headlong into poor decisions and lots of consequences. My eldest child, who is now a full-fledged adult, taught me about leadership. Though he was the youngest in the play yard when starting kindergarten, he was also the organizer of most of the games. Today, he is dutiful, loyal to a fault, and can plan an international travel trip or sports league match with practiced skill.

Each September, I am reminded how far I’ve come as a parent and an educator. I like to call my parenting “the three-kid shuffle,” and my classroom time “the distillery.” Some kids enter school cautiously, while others bring on the bravado while unfolding in ways that tell the uniqueness of their stories.  What matters most as a parent or teacher is that you settle into the possibility (and uncertainty) of it all. Resist managing the outcome and lean into the natural evolution that comes with raising and educating children. After all, isn’t that what school’s September kick-off is really all about? 

Barbara H Scott is the Executive Director of Parents League of New York.  Prior to Barbara’s leadership at PLNY, she served as a school admissions director, preschool head, and classroom teacher in a variety of settings. Deeply committed to a range of other organizations that aim to serve the community, Barbara sits on the boards of The Association of Boarding School (TABS), Central Park Conservancy’s Women’s Committee, and the Making Caring Common Project at Harvard’s GSE. She is also the board chair at Bronx Charter School for the Arts. Barbara earned a BA at Hamilton College and an MA in private school leadership from the Klingenstein Center, Teachers College, Columbia University.