When a teacher reaches out to discuss your child, it rarely bodes well. Sometimes, you might hear, “Your child is exceptionally talented and we need to start preparing him for a speaking engagement.” More often than not, though, it’s not the news you hope for.
This call was no exception. Sitting at my desk, buried in paperwork, my son’s kindergarten teacher shared what I had already feared: he was struggling. Learning and writing letters was a challenge for him, and he didn’t grasp the various consonant sounds. Frustration was evident.
His initial months of school were rocky. He resisted attending class, argued with his sister, and was irritable with the babysitter. It was disheartening to see him start putting himself down.
My son was born in November, making him one of the youngest in his class. He was barely four when he began kindergarten, while his classmates were celebrating their sixth birthdays. Just a few months prior, he had been in preschool, playing with blocks and trucks. Now, he was expected to identify letter sounds and write them down. It was no surprise he was falling behind.
We had toyed with the idea of “redshirting” him—essentially delaying his entry into kindergarten to allow for more social and academic growth. Our pros and cons list leaned heavily toward sending him to school. His preschool teacher believed he was ready, and we worried he’d be bored if he stayed back, especially with his friends advancing. Plus, the financial strain of another year of preschool was a consideration.
The only downside? He would be younger than his peers.
I underestimated the weight of that one con. My daughter, born in April, was right in the middle of her class age-wise, so I didn’t fully grasp the impact of those extra months. Watching my kindergartner struggle was painful. It hurt to see him come home feeling defeated, with his excitement for school fading and his self-esteem taking a hit. Hearing him criticize himself for being unable to do things that perhaps a four-year-old shouldn’t be expected to do was heartbreaking.
During that phone call, his teacher laid out a plan for support: he would receive extra help in the classroom and occupational therapy to improve his pencil grip. She promised to check in with us at the next parent-teacher conference to assess his progress. I felt a wave of relief wash over me; it didn’t seem too daunting. I appreciated that his teacher was proactive and tried to stay hopeful.
To my surprise, things did improve. After our meeting, while his work still resembled abstract art, his teacher reported significant progress. My now-five-year-old returned home eager to share his discoveries, sounding out words and identifying letters. With his growing math skills, I wouldn’t be surprised if he’s doing our taxes one day. Although getting him to focus on homework remains a challenge, I recognize the advancements he’s made.
Did we make the right choice? It’s difficult to say as we await his continued progress. Part of me feels we may have deprived him of a carefree early childhood. There’s also the guilt of introducing him to stress and self-doubt at such a young age. Was this all necessary?
I may never know what it would have been like if he had stayed in preschool, potentially facing boredom while his peers thrived. However, children are remarkably resilient. He’s back to being our cheerful, playful little boy, even catching me when I attempt to shortchange his allowance. He’s maturing, acting more like the older kids in his class.
Perhaps, for now, that’s the real loss.
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Summary
Reflecting on the decision to send my son to kindergarten at an early age, I realize the challenges he faced in adjusting and learning. While we believed we made the right choice, the struggles he experienced led to feelings of guilt and uncertainty. However, with support and time, he has shown significant improvement and resilience, reminding me of the complexity of parenting decisions.

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