Rosa Balestrino has lived in Westport since 2016. The mother of 2 children, ages 13 and 5, she is in-house counsel to an educational technology company.
The family worships at Assumption Church, and are huge fans of the Westport Weston Family YMCA, Legacy Martial Arts, Compo Beach, the Levitt Pavilion and Westport Library. Rosa writes:
In 2018, our journey with Westport Public Schools began with a simple recommendation to postpone kindergarten. What followed was a years-long trek through evaluations, diagnoses, inability for my child to learn virtually, and the heavy isolation of the COVID-19 pandemic.
For years I struggled to square the child I saw at home — who could focus for hours on intricate Lego sets — with the child who was reportedly “failing to attend” in class.
At home, getting him to write a single sentence was a battleground of exhaustion and heartbreak. I could not understand why.

Rosa Balestrino
During the pandemic, I worked alongside my child and had a front-row seat to his ongoing struggle, frustration, and inability to do the work that was being requested by the school district. It was so painful for both my child and for me.
My child’s struggles went on for years. My gut instinct told me that something was wrong, even though the school continued to reassure me and encouraged “independence” for middle school.
My child could not even start an assignment alone, let alone finish one. Tears, frustration, my child thinking he was stupid. It was heartbreaking for a parent.
Since the school had not figured out why my child struggled year after year, I had no choice but to have a private evaluation done at my own expense.
The neuropsychologist made clear that if my child had the “capacity to become independent, he would have already done so.”
My son was failing, and was being failed by the school system who tried to assure me that my child was doing “fine.” They stated his grades, which were As and Bs, were proof of success, and that his low standardized test scores were merely “data points” or “click-through” errors.
At that point my son’s handwriting remained the scrawl of a 1st grader. External tutors warned us his comprehension was years behind grade level.
The turning point for my child came when we stepped outside the traditional system. Through an intensive summer program at The Southport School and eventually transitioning to Winston Preparatory School, the “magic” happened.

For the first time, my son felt capable. Within 2 months of starting 7th grade at Winston Prep, he volunteered that he loved school. He couldn’t quite explain the “magic” of how they taught him — only that for the first time, he was actually learning and he no longer felt stupid. His whole demeanor changed.I started to get my child back.
The cost of this “magic” was high. It required an educational attorney, expensive private assessments, and the difficult decision to leave the neighborhood school.
Today my child is thriving, advocating, and looking toward a future in engineering. My child has found his community through neurodiverse mentors who taught him that his brain isn’t broken—it’s a superpower.
To the families currently in the “exhaustion phase”: Trust your instinct.
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