Dear kindergartener, here’s what your parents need you to know

Jackson getting on the school bus for his first day of kindergarten

One week ago, Ashlee and I — armed with tissues — put Jackson on the school bus for the very first time as he headed off to his first day of kindergarten. We were worried he’d panic at the big moment and we’d have to carry him screaming onto the bus; thankfully, his affinity for all things with wheels had him literally running to be first in line, with barely a glance back at his teary-eyed moms. 

We had been preparing him for weeks: We got all the “Night Before Kindergarten” books, let him pick out his school supplies, talked all about what he could expect, had “Full House”-style heart-to-hearts about the value of change. Yet, as big and scary as this has certainly been for him, what no one tells parents sending their oldest off to kindergarten is that it’s just as much a mindf*ck for the parents. 

We got our first taste of this last month at a “meet the principal” event with his fellow incoming kindergarteners at their new school — all 275 of them. Ashlee and I were aghast at the sheer number of little people running around, screaming, falling on the playground, getting lost, crying. I stared out at the sea of tiny humans and it hit me: He’s going to be with these kids for the next 13 years. One of them could be his lifelong friend, someone may be his prom date, one of these kids could even be his spouse. And likely, one will be his bully, one will make him feel bad about himself, one will walk down a bad path with him. Home schooling looked really good right about then. 

Later in the summer, Ashlee and I were nail-biting on the couch: What if he gets lost getting off the bus? How will we know if he’s being picked on? Is it illegal to put a tracking device on your kid’s backpack? Tears welled in Ashlee’s eyes: “This is when the drugs start,” she whispered. 

We knew we lost it. But it’s just because we care so damn much about this little person we have to send out into the world. And sure, kindergarten isn’t exactly a war zone, but it’s his biggest step yet out of the protective little bubble he’s lived in for all of his five years — and it’s terrifying for us.

But as parents, we don’t want him to know that. We’ve been focused on making this transition a positive, exciting one — but, in the coming weeks and months, there are some important truths I am going to need to share with my new kindergartener. Here’s how I’m rehearsing it: 

There’s bad in this world 

In just a few short weeks, you’re going to hear the phrase “active shooter drill” for the first time. Those words are going to have you looking at the people around you, the spaces you’re in more skeptically than you ever have. You’re going to have to go from learning your “ABCs” to learning when to “run, hide, fight.” 

I’ve turned the news off so many times when you come into the room because I haven’t wanted you to face the reality that there are bad people in the world — not just in your superhero stories — and that bad things happen sometimes for no reason at all. But it is there. And now we have to figure out how to prioritize seeing the good while not ignoring the bad. 

Ignorance and intent don’t always go hand in hand

When you talk with your new friends about your two moms, someone may not understand, or someone may even laugh. While I have some four-letter words for those kiddos, I’ll save those for after you go to bed, and tell you instead about the word “ignorance.” It doesn’t mean that other kids want to upset you or make you feel bad — they may be coming from a world where they’ve never seen a family with two moms. And from kindergarten until you’re an old, balding man, you’ll see that when many people encounter something new, different or something they don’t understand, they may act out.

But differences abound — some kids in your class will have one parent, some kids have glasses, there are kids of every skin color, some have short hair and some have long hair, you all have different strengths and abilities, and you will all learn in different ways and at different paces. And that’s wonderful! And, unfortunately, it takes some kids and their parents longer to see that.

You won’t be perfect — and neither will every day 

Jackson sits on a step with his siblings, August and Avery

I wish I could help every day of kindergarten be a breeze for you, but I can’t—and it won’t! And that’s OK. You saw that on just your second day when you tried holding it all day because you were nervous to ask to go to the bathroom. But the world kept spinning. You’ll make mistakes, and other kids and even teachers may make mistakes that will affect you. And sometimes, there will be things out of your control that may ruin your day: It’s going to rain at recess and your stupid egg allergy may make you the only kid in the class who can’t eat Mackenzie’s birthday cupcakes. But you’ll always bounce back — and believing that makes it easier to deal with the hard things to come. 

We’ll help you stay yourself

Elementary school is an amazing time to learn about what makes you unique — but it can also be a time when peer pressure creeps in. And as parents, we’re going to do all we can to remind you to stay you. You’re the goofy little boy who loves “time traveling” in Amazon boxes, who needs to wear your “blanket ears” to go to sleep, who is convinced peanut butter comes from acorns, who thinks Teenage Mutant Ninja Turtles are the best thing in the world and that a mysterious key hanging by our front door unlocks the secrets of Narnia. We don’t want you to lose any of that magic that makes you you! That’s why, during kindergarten clothes shopping at Target, when you picked out that outrageous multi-colored tiger shirt and the two-toned shorts you just loved (and that transported us back to a 1980s “Saved by the Bell” episode!) Mom nodded and threw them right in the cart. When you feel the pull to fit in, we’re going to be here to remind you of everything that makes you special.

It’s time to fly, but you’ll always have a home base

A few weeks ago, when you met all of your fellow kindergarteners for the first time, I know you were overwhelmed. Amid that teeming sea of 275 kids, all I could see was you, as you stood in the middle of the playground, nervously chewing your shirt and slowly turning in circles, not quite sure how to talk to the other kids. I’m sure I wasn’t the only parent on the sidelines exercising every bit of my self-control: I spotted one of your fellow preschool friends and wanted more than anything to grab him by the hand and say, “Play with Jackson!” That probably would have gotten me arrested … and also wouldn’t have let you stand on your own. Because even if it’s overwhelming, that’s what kindergarten is all about!

And really, that’s what the last five years have been about. From learning how to soothe yourself to sleep as a baby to falling off and getting back on your bike as a toddler and, now, to climbing onto that school bus without your parents, each step you take by yourself is a building block to let you become who you’re meant to be. (And this is as much a message for your parents as it is for you.)

However, while we want to give you the space to fly, you always have a place to come back to. That day on the playground, when you ran up to hug my leg and yelled “Mommy!”, I knew we’re your safe space. And that’s what we’ll continue to be. When you’ve held in too many emotions during the day or the real world of kindergarten just isn’t making sense to you, we’re here. 


Ideally, this is how our conversations would go. But, considering that all Jackson cared to talk about during his first week was the inner-workings of the school bus — and he got technical, from the lack of seatbelts to how the speaker system functions! — it will likely be tough, but we’ll get there. Just like we’ve gotten through the rough spots of the last five years: one step at a time, together.

Jackson smiles with a frame around his head stating "PROUD TO BE A GOLDEN BEAR"
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