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    September 8, 2026
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    Home»Money»We Redshirted Our Son for Kindergarten. Then He Skipped a Grade.
    Money

    We Redshirted Our Son for Kindergarten. Then He Skipped a Grade.

    Press RoomBy Press RoomSeptember 8, 2026No Comments5 Mins Read
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    Redshirting my son was based on a technicality.

    He was born in Maryland, a state where children must be 5 before September 1st to enter kindergarten. With his late October birthday, he was ineligible on the cusp of his 5th birthday. Instead, he entered pre-K through the Montgomery County Public School system.

    It was the fall of 2020, six months into the COVID pandemic. Even virtually for most of the year, he learned so much from his amazing teacher.

    When we moved back to New York ahead of the next school year, we had a decision to make.

    We held him back

    In our Hudson Valley town, the kindergarten cutoff was December 1st. Had we moved the year before, as planned, he would have started kindergarten on time, but with the two different cutoffs, we had to choose — should he start in his age-appropriate grade, entering school as a first grader, or should we hold him back and start him in kindergarten?

    After lengthy discussions, we decided to send him to kindergarten. It’s a special school year, and we chose to give him that gift.

    When he started school, my son was two months away from turning 6. Not only was he one of the oldest in his class, but he was also nearly a foot taller, too. Right away, we questioned whether we had made the right decision. He was thriving, for sure, but it became clear early on that the different cutoff dates were reflected in the curriculum. Kindergarten felt very similar to what he had already done in pre-K.

    During my daughter’s kindergarten year in Maryland, she spent the first few weeks reviewing the basics before diving headfirst into academics. For my son, the pace was slower. While my daughter hit the ground running, my son took a more meandering path into academics.

    He was ahead of his peers

    All things considered, he had a fabulous kindergarten year. He went apple picking and to the zoo. He listened to stories, made crafts, and celebrated the 100th day of school. He had friends and was happy. He was eager to learn, but at times, was frustrated by the pace of instruction. He was ready to go, go, go. During parent-teacher conferences in November, his teacher informed us that she was already giving him supplemental worksheets to keep him busy and engaged.

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    Boy posing for photo at school

    The author’s son was ahead of his peers in kindergarten. 

    Courtesy of the author



    By the time he reached first grade, it was clear that he was significantly ahead of his peers academically. We grew worried about boredom and behavior. When we discussed our concerns with his teacher, she agreed with our assessment that first grade was not the right place for him.

    Having gone through early elementary with our daughter before, we knew that while the jump from first to second seemed doable, the jump from second to third, with the increase in academic rigor, did not. If we were going to do it, this was the time. With his teacher’s support, we reached out to the principal and began the process of moving him up a grade.

    He then skipped a grade

    It took longer than we’d hoped, but halfway through the year, with months of data from his teacher and evaluations from his school’s academic support staff, he transitioned from first to second grade.

    The move went better than we could have hoped. He joined second grade just in time for a trip to the aquarium, and another mom sent me photos from the trip, my son seamlessly integrating into his new class. Academically, he went from being significantly ahead to being right on target in most subjects, with a little catching up to do in others. As he progressed through the rest of elementary school, he caught up and pushed even further. At a school event this past year, one of his classmates felt compelled to tell me that my son was, like, really smart.

    Now on the verge of middle school, I’ve reflected a lot on the choice we made. Even though the decision to redshirt was largely by default, I was always uncomfortable with the concept. Red shirting is a privilege. The “gift of time” that proponents of the practice espouse is one that many families can’t afford. And while there are legitimate reasons to delay kindergarten, none applied to my son.

    We could have kept him where he was, giving him the advantage of age, size, and academic achievement, but it felt unnecessary for our family. My son is the child of two college-educated, middle-class adults. He’s been in the 90th percentile for his size since birth. He didn’t need the extra help red-shirting could provide.

    By moving to his age-appropriate grade, my son was able to flourish. Rather than coasting through school, he was challenged. He never lost his excitement and curiosity for learning. He has great friends and an active social life. And he’s ready for the next step on his academic journey.

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