A tender dispatch from the edge of a new beginning.
This week, I dropped my 14-year-old son, True, off for his first day of high school.
He’s been a Waldorf kid since Kindergarten. For nine years, he’s been deeply held in a school community that values creativity, slowness, relationship, and soul. There’s been no tech at school, no traditional textbooks (they make their own), no school cafeteria (they eat together in class with their teacher). He’s known every teacher by name. Grown up with the same classmates. Learned through stories and music and connection. And now, suddenly, he’s in a completely different universe.
A brand new school. Not a Waldorf high school. A public high school where he doesn’t know a single soul. Everything is unfamiliar. The rhythm. The culture. The environment.
And all kinds of parts of myself have been stirred.
The part that is excited for him to explore new terrain and carve his own path.
The part that is terrified he’ll get lost or feel alone.
The mom part that is trying (and failing) to be chill, while also staying vigilant, because he’s walking into a world so vastly different from the one he’s known and loved for so long.
It’s been a lot to hold.
I remembered this week that on his very first day of Kindergarten, I gave him a little heart-shaped rock with the word brave written on it. He tucked it into his tiny pocket and off he went, five years old and wide-eyed, into that first classroom.
This time, on his first day of high school, I had the same instinct. To hand him that same heart rock, quietly, just before he walked out the door. But I didn’t.
Because, well… he’s 14 now. Taller than me. Stretching into his own edges. Figuring things out. I could feel that offering the rock was too sentimental. Too mothering for a boy stretching his wings.
So I held back. I’m learning part of letting go means trusting he already carries what he needs.
As I watched him cross the threshold of the school building, swallowed up in a sea of unfamiliar faces, I found myself holding a very particular ache of motherhood.
Despite my deep confidence in who he is, there is also terror here. A bone-deep vulnerability that rises when our children step further into the world. A world we cannot shape or shield in the ways we once did. Will this new world be kind to him? Will he find his people? Will the teachers see him, attune to him, hold space for his brilliance and his sensitivities?
My heart drops, knowing that the way I get to show up as his protector has already shifted. I’m not on the inside of it anymore. It’s a particular rite of passage I hadn’t anticipated. And it feels achy.
When I picked him up on that first day, his face said everything. It was a hard day. He wasn’t prepared for how vastly different it was from the school community he’s grown up in. The culture shock. The overwhelm. The absence of rhythm and familiarity. He let it out, and I listened. And a familiar truth became truthier than ever: I can’t fix this. I can’t shield him from the discomfort of this new chapter. I can’t make it easier.
What I can do is hold space. I can stay grounded in my presence. I can ask gentle questions (but not too many. He’s 14, after all). I can normalize his experience and validate that yes, this is hard. This is disorienting. And he is not alone.
But I cannot swoop in and soften the edges. And that is a particular kind of pain I wasn’t fully prepared for.
There’s a line from John O’Donohue that I’ve been carrying like a talisman this week:
“You have traveled with him to the shore of his own freedom.
Yet still, it is hard to turn and leave him on that lonely shore.”
Just outside my studio door, four baby birds have fledged. I’ve been watching them all week as they sit on the porch railing, hesitating, gathering courage to do what is in their nature to do: fly. And then, one by one, they leap. Wobbly. Squawking. Practicing. Returning. Trying again. They are going to see the big wide world that called them here in the first place.
And I know that True is doing the same.
As he makes his way into this new beginning, I’ve been whispering a few blessings. Mostly to myself, but also to the unseen forces I hope are walking beside him.
May good, loving people find their way onto his path.
May he see them, recognize them, and connect.
May he surprise himself with new adventures.
May the tender, essential parts of himself be honored, not tucked away to fit in.
May his curiosity outshine his fear.
May he trust this season of his life, and follow the paths that spark joy, always.
And may I keep learning how to let go, too, one small moment at a time.
