FEELING: Ache.

As Leo prepares to start big school, I confront the fear beneath this milestone: that helping my son grow also means slowly learning to let him go.

Letter no.43 - August 25th 2026

Dear Leo,

Was that our last camp before you start big school?

I found myself wondering that as I packed everything away. Rolling up sleeping bags, folding down the rooftent and reluctantly putting our things back into our bags that somehow never seem quite big enough on the journey home.

It felt like the end of something. Not camping. We have years of that ahead of us.

But the end of something. 

In a few days, you start big school, and I need to be real with you on how I feel about this. I am nervous, apprehensive, worried, all of it. 

People keep telling me how quickly it goes from here. They say you start school, become a proper kid, then a teenager, and before we know it you will have packed your own bags and flown the coop.

They say it casually, usually with a smile.

I don’t find it particularly comforting, at all. Because I’m not ready to lose my innocent little boy. The boy who still reaches for my hand. Who asks me (and Mum) to stay beside him until he falls asleep. Who thinks an afternoon riding bikes with Dad is a perfectly good way to spend a day.

I know you aren’t disappearing when you walk through those school gates. But I also know that a slightly different boy will walk back out.

Your world is about to become bigger, and for the first time, I won’t be able to see all of it. There will be conversations I don’t hear. Games I don’t understand. New words, new ideas and new people influencing the person you are becoming.

Will the other children be kind?

Will their parents be people we understand?

Will somebody make you feel small?

Will you have the confidence to tell us if they do?

And then there is the question I keep returning to: have we chosen the right school?

It is an enormous commitment for our family. Financially, it scares me. Have I pushed myself too far? Have I allowed my fear of getting this wrong to persuade me that an expensive choice must be a safe one?

Or is this just what it feels like to give your child an opportunity you didn’t have yourself?

I don’t know yet. I’ll circle back to that point down the road I guess. 

That is one of the more uncomfortable discoveries of parenthood: the biggest decisions often have to be made before you have enough information to know whether they are right.

We visit the schools. We meet the teachers. We ask questions, compare values and study the details. Then we choose a door and send the person we love most in the world through it.

After that, a certain amount is beyond our control.

I recently came across a book called The Gardener and the Carpenter by Alison Gopnik. She suggests that raising a child is less like building a piece of furniture and more like tending a garden.

A carpenter begins with a plan. They measure, cut and shape until the material matches the picture in their mind.

A gardener does something different.

They prepare the ground. They provide light, water, shelter and space. But they cannot dictate exactly how something will grow.

I think I have spent a lot of time trying to be both. I want to give you good soil, but I also want to protect you from every storm. I want you to grow into yourself, while quietly hoping that the person you become still wants to come camping with me.

Perhaps that is what I am really frightened of. Not school itself, but what it represents.

This is the first significant step you will take into a life that belongs to you.

Until now, I have been able to stand very close. Close enough to catch you in the pool, steady your bike and translate the world when it feels confusing. Big school asks me to take half a step backwards. Not because you need me less, but because you need enough space to discover what you can do without me.

There is a line by Kahlil Gibran which says that our children come through us, but do not belong to us.

I think I understand it a little more now.  I’m just not sure I’m ready for it.

Maybe I am holding on too tightly. But I would rather loosen my grip slowly and consciously than pretend this moment means nothing to me. My job isn’t to keep you little. It is to make sure you feel secure enough to grow.

So, when the day comes, I will straighten your uniform, take too many photographs and walk you to the gate. I’ll tell you how exciting it is. I’ll smile so that you know there is nothing to be afraid of.

Then I will let go of your hand.

You will walk forward.

And I will begin learning how to love the next version of you, while quietly missing every version that came before.

Always,

Daddy x