On the first day of school, my second-grader barely tossed me a backward glance as she bounded into the classroom, ever the confident veteran student. She’d done this school thing before, a few times now, and she slid easily and eagerly into another highly anticipated school year. 

No problems there.

But my newly-minted kindergartener? I’m afraid that’s an entirely different story. 

Maybe it’s because he’s the middle child, or a boy, or something to do with having three sisters, but my son is a natural-born skeptic. Whenever circumstances are unfamiliar, his guard immediately goes up and I can all but see the warning lights in the control center of his brain start flashing in urgent unison. He’s cautious—had to be coaxed out of the womb even—and a creature of unflappable habit. 

It’s why on his first day of kindergarten, I was pleasantly surprised and a little shocked at how smoothly it went. 

He was quiet, naturally, taking it all in as I walked him across the speckled tiles toward a pint-sized table. When we stopped together at his tiny blue chair, I braced myself for tears. 

And there were tears—but they weren’t coming from my son. 

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Across the table sat a little girl, a slip of a thing with mousy brown hair and a deep summer tan. She was dressed in her Sunday best, hands in her lap, feet firmly on the floor—motionless, and silently sobbing. 

My heart lurched. Oh no. Ten more seconds and we were going to have a table full of weepy 5-year-olds wondering why on earth their mommies and daddies had abandoned them for six hours in this strange new world. 

My son eyed his table mate warily as I tried to smooth it over. “This is Nolan,” I said a little too brightly as I knelt down to their level. “I think he’d like to be your friend!” 

She sniffled. Nolan stared. I stammered something about “wonderful day have so much fun,” squeezed my son’s shoulders, and hightailed it out of the room before I lost my nerve and took the entire class out for ice cream instead. 

Outside, I cautiously congratulated myself. He didn’t cry! He did just fine. He’s going to be fine. I’m going to be fine. 

Whew. 

But then, day two dawned, and we had to do it all over again. 

And he wasn’t fine. 

Maybe he thought it was going to be a one-off, this kindergarten thing. Because when we pulled up to the school the morning of day two, he dissolved into tears. Kicking, fighting, wailing, gnashing of teeth, the whole nine yards. 

I crumbled as I wrestled him out of the car with diminishing resolve. 

Inside, his teacher met us with confidence. “I’ll take him,” she instructed kindly, arms outstretched. She’d lugged forty pounds of five-year-old through those doors a time or two before, no doubt. 

I handed off my sobbing son, watched the door shut behind them, and cried all the way home. 

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A few hours later, the teacher sent me a picture of my son. Smiling. “He’s doing great,” she wrote. “See you after school!” 

I’d like to tell you that from that moment forward, it was smooth sailing, but the truth is, it wasn’t. We struggled on many mornings, none quite as dramatic as that second day, but hard nonetheless. 

Two shiny pennies turned it around.

Before school each morning, we picked out two gleaming coins from the box that collects loose change in our house, the shiniest ones we could find in the bunch. 

“You put one in your pocket, and I’ll put one in mine,” I told my son. “Whenever you feel lonely or scared, touch your penny. I’ll keep one in my pocket and whenever I feel lonely or scared, I’ll touch my penny.” 

He considered this idea for a moment with a furrowed brow, then nodded almost imperceptibly. 

It did the trick.

My son told me on more than one occasion, shyly at first, that he’d reached into his pocket to hold his penny—and it made him feel better. 

I confessed I was at home doing the very same thing, and probably more often than he was.

Eventually, we both settled into the new normal and didn’t worry about having pennies in our pockets at the start of the day. They had done their job, giving us both a little extra comfort in the next step of growing up. 

In a few days, my son will be a first grader, a whole year of school under his belt as he walks through the doors. I hope his confidence has multiplied in those 12 months, that this second time will be smooth and eagerly anticipated. 

But I’ll have a couple of shiny pennies on standby—just in case.