My Baby, the Kindergartener

In the Boston area, many of us are lucky enough to live in “walk-to-school” neighborhoods. My family just moved to a new house a mile from our kids’ elementary school. And in just a few days, my 5-year-old and I will embark on the first of many walks to school. Because she’s about to start kindergarten. Gulp.

My baby the kindergartener

A friend of mine once said there should be a word to describe the emotion you feel when you watch your child walk into a school for the first time. I think I know what she means. I’ve seen my daughters off to enough daycares and preschools to recognize that familiar mix of excitement and sadness, pride and worry. Oh yeah, there’s always worry. No matter how confident you are in the care and education they’re receiving, you worry. They’re no longer in your nest, cozied up under your wing. They’re flying, and it’s scary as hell.

I remember well the first time one of my babies left the nest. I was working full time back then, and the day arrived for my infant daughter, Sloane, to head off to daycare. That, too, was a short walk away, and as we set off slowly, I stared down at little Sloane in my carrier and kissed her forehead. I reluctantly handed her over to the kind women at the local daycare, and as Sloane dissolved into tears my own chin quivered violently. I quickly turned away, eyes stinging, clutching the telltale Medela pump bag to me. And away I went.

Did it get easier? Of course. Did I come to appreciate how much nurturing and socialization Sloane was getting out of her daycare? Indeed. And did I relegate my thicker-skinned husband to teary drop-off duty whenever possible? Yes. Yes, I did.

And now another September is upon us, and that same little girl, my first baby, is about to start kindergarten. Kindergarten. The real deal. And that familiar feeling is back, but this time with a vengeance. All summer long I’ve tried to ignore it, focusing my energies on selecting the most Sloane-esque Pottery Barn Kids backpack, pairing bento boxes with lunch bags, labeling her clothes. We’ve driven past the school, checked out the playground. I hit the Lands End back-to-school sale hard this year, and when the boxes arrived, it was like Christmas at our house. Sloane entertained the whole family with a fashion show of leggings and cardigans.

But now all that is done, and the first day of school is almost here. We’re just about to the front steps of the school. Her little hand is in mine. And we walked the whole way there together.

A Maine native, Jessie migrated down the coast to Boston after college, and it’s been home ever since. In this great city, Jessie met her husband, graduated law school, played in numerous basketball leagues, worked as a marketing writer, ran the marathon, lived through several home renovations, and wrote many beginnings of many books. But of all these great adventures, she most loves the one she’s on now: on-the-go-mom to three energetic and hilarious daughters. Jessie, her husband, and their trio of little ladies live in Brookline.