Trusting Ourselves Enough to Let Go

I had an unexpected moment in the grocery store today.

As I wandered the aisles, I kept crossing paths with a young mother and her two little children. More than once, one of them reached for a snack on the shelf or pleaded for something sweet, only to hear, "No, you can't have that. I love you and care about what I put in your bodies."

Those words stuck with me.

Not because I disagreed with her. Every parent gets to decide what's best for their family. But as I glanced down at my own cart containing Triscuits, a box of Life Cereal and a big box of Cap'n Crunch Berries, and regular (e.g. not organic) skim milk, I found myself feeling oddly self-conscious. Was I somehow sending a different message about how much I cared?

Then it hit me.

Parenting isn't measured by what's in our grocery cart. It's measured by the thousands of moments that make our children feel safe, known, encouraged, and deeply loved.

The same thought often comes up when I work with families considering boarding school.

Many parents worry that by sending their child away to school, they're somehow loving them less or giving up control. In reality, the opposite is often true. Choosing a boarding school isn't about stepping back. It's about stepping alongside your child and trusting that you've given them the foundation to grow. It’s not “sending your kid away” but rather “providing them with opportunity.” 

Just as we can't control every food our children will one day choose, we can't protect them from every challenge they'll encounter. Our job isn't to manage every decision forever. It's to help them develop the confidence, judgment, and resilience to make good decisions when we're not standing beside them.

Whether we're choosing cereal in the grocery store or considering a boarding school education, there isn't one perfect path. There are simply thoughtful parents doing their best.

Sometimes, the greatest gift we can give our children isn't tighter control. It's the confidence that they are ready to try new things, knowing they always have a place to come home to. As I tell many parents, when my parents chose boarding school for my brother and I years ago, it was one of the greatest gifts in my life they gave me!