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The first day of school is hard. It’s hard on the kids, the teachers, and the parents. But there is a sense of ease once a child is acclimated to their school. A familiarity and community. New friends and all new experiences. Once parents stop worrying about their children being away from them, they also feel a sense of calm. They are on their way to a successful school year — and a year closer to becoming who they are going to be for their lives.

But kindergarten? 

That’s unexplored territory. That is the hardest transition for a child, especially one who has been home with parents or a nanny for the past five years. It is tough for a child who attended preschool for three hours a day to make it through a full school day. It can be jarring for a child who attended a full-day, play-based preschool to sit in an assigned seat and complete their work without chatting. My youngest is starting kindergarten this year, and although she attended preschool last year, it was only for a few hours a day. This is going to be the hardest transition.

And then there’s high school…

Talk about HARD. Your child is now expected to basically be an adult. There’s no cutesy PTO to get you to participate in the fun run. There’s no pick up and drop off where parents chat. Teachers email parents last, after working with the child to solve their problems. My son starts high school this year. He is going to a vocational high school in the next town over. I have no idea what his teachers are like. My oldest just finished his freshman year, and I can’t tell you a single teacher’s name. I feel so disconnected. This is the HARDEST transition.

But wait. Kindergarten includes a cafeteria. 

Like, an entire school eating lunch in the same room. And a lunch line — how will she know what she wants to eat for lunch?! Is she even old enough to legally BUY anything? Does someone make sure she doesn’t throw away her Tupperware and water bottle — is that a thing in kindergarten? She might forget where her classroom is when she goes to the bathroom. Does she know how to use a bathroom stall? I wish she were older.

Oh, NO. I didn’t mean high school “older.”

The high school is like its own city. There are hallways for different grades and subjects.  There’s a gym, theater, cafeteria, meeting room, and three offices. There are no teachers to walk them through these new halls and remind them to stay single file down the hall.  And there’s also a café with a menu for lunch. I have no idea what is even served, so I give my kids money and hope they figure it out. Thrown to the wolves. High school has to be the most difficult place to get acclimated.

Unless you compare that to kindergarten.

You get this list of all the supplies your child will need for the year. And you get six extra boxes of crayons, because what if your kid is the one who eats them? Do you send them all in and they get put in a community crayon box? What if your kid eats all the yellow ones — can you even just buy one color? You better buy 10 boxes, just in case. Supplies are tricky to sort out in kindergarten.

And in high school, supplies are immensely difficult to manage.

A $25 binder that is the specific color, shape, size, and dimensions the biology teacher requested? No problem — grab that one and the 300 dividers and 30 packs of looseleaf paper. The only problem is that in June, these will either come home crushed and folded and beyond repair… or… they will come home never used and the wrong color for next year’s English lit class.

OK, OK. So I guess both kindergarten and high school are really tricky situations. And it’s clear to see what the most difficult transition tends to be — it’s being a parent and sending your child off to school that first day. There’s joy in getting another set of hands to help mold them, and there’s heartbreak watching them grow so fast. There’s excitement for them to make friends and join new activities, and disappointment in them needing you less.

The first-day-of-school transition is the hardest transition. Our hearts, as parents, are so full of love for our children. And we are met with a wave of inconsistent feelings every September. “Wow, look at the person they are becoming” meets “Wow, how can these years go by so fast?” So, say hi to those teachers, put trust in the lunchroom, and grab those supplies. It’s all hard. But it is all fantastic.

Michelle Mady
Michelle is a lifelong New Englander who lives in Stoneham and works in Charlestown. She is a preschool teacher and Assistant Director at a small private preschool and holds a master’s degree in early childhood education, which has come in useful at both work and home. She has a supportive stay-at-home-dad for a husband and is a mom of five children. She has three boys born in 2005, 2007 and 2008, plus two girls born in 2012 and 2015. Michelle teaches infant and toddler classes for early education teachers and is an adjunct professor for The School Of Mom. She also runs her own business, The Parenting Survival Expert, offering parenting tips and support. In her spare time, she can be found reading a murder mystery novel, sipping far too much coffee, and dreaming of a home in the mountains.