FEELING: Reflection

I thought this letter would be about Leo's final sports day at nursery. Instead, it became a reflection on something far more uncomfortable: the invisible expectations we place on the people we love most, and how easily our own relationship with pressure can become part of their story.

Letter No. 37 - June 30th 2026

Dear Leo,

This week, I want to do something I've never done before. Usually these letters stay between you and me, and this one still does.

But for the first time in thirty-seven letters, I'm not going to finish with a lesson. Instead, I'm going to ask for one.

Not from you. From every parent reading this.

I came home from your nursery sports day this weekend wondering whether I'd made one of the first real parenting mistakes of your life.

Not a dramatic one. And hopefully, not one you'll ever remember.

But perhaps one I'll never forget…

Your final sports day at nursery had been building for weeks. You'd been practising with your friends, telling us about the races, explaining who was fast and who might win.

Watching you grow has been one of the greatest privileges of my life. You're naturally energetic. You throw yourself into almost everything. You learnt to ride a bike quicker than I expected. You took to skiing with a confidence that amazed me. Whether it's firing your bow and arrow across the living room, scrambling over the play park apparatus or chasing a football around the park, your body seems to understand movement instinctively. So much so, Grandma recently made the observation that you move like a 7 or 8 year old, which is a compliment to you.

And I'd be lying if I said that doesn't make me smile.

Every parent hopes their child will experience opportunities they never had. Not because they need to become exceptional. But because we all want life to feel a little lighter than it did for us.

You have a confidence at four that I don't think I found until my twenties.

You're expressive. Funny. Affectionate. You make friends wherever you go. You happily walk up to strangers and give them a spud.

So perhaps that's why Saturday caught me completely off guard.

For months now you've been obsessed with football. The World Cup has captured your imagination and EVERY match brings the same question.

"Dad... can I have football boots like theirs?" The ones without laces.

So I made what felt like a harmless little agreement.

I told you that if you listened carefully, concentrated, gave everything a go and tried your hardest at sports day, you just might win and afterwards we'd go and buy your very first pair of football boots together.

At the time it felt like encouragement. A memory we'd both treasure. Just like buying our matching Swatch watches together after our first ski trip to Morzine.

But over the last few days I've realised something. Somewhere along the way, the football boots stopped representing effort. They became attached to the outcome and it distracted you from the innocence and enjoyment of sports day. 

I never intended that to happen.

But in my own mind I'd already imagined the day. I'd imagined you running. Feeling proud of yourself. I'd imagined us driving to the sports shop afterwards.

I had written a story that hadn't happened yet.

When we arrived, parents, grandparents and siblings lined the edge of the park. From where I was standing, it looked lovely.

From where you were standing...

It must have looked enormous. Suddenly there were dozens of unfamiliar faces. People watching. Teachers organising. Children waiting. Noise everywhere.

Pressure has a funny way of making even the smallest moments feel much bigger than they really are.

I know that feeling. Even at nearly thirty-six years old I still do.

For most of the children, it was exciting.

For you...It was overwhelming.

You froze. You didn't want to run. You just wanted Mum and me.

Standing there, watching you cling to us, something shifted inside me. I realised I wasn't disappointed in you. Not for one second. I was disappointed in myself.

Not because you didn't run.

But because somehow I'd allowed a tiny nursery sports day to become something much bigger inside my own head.

Sports day doesn't matter. It really doesn't. I wasn't desperate for you to win. I just wanted you to enjoy yourself.

To finish nursery feeling confident before the next big chapter begins in September.

But you're four years old. You're carrying emotions you don't yet have the words to explain. And somehow I'd briefly forgotten that.

Since Saturday, I've done what I always do when I don't have the answer.

I started reading and research around four-year-old boys and the transition into school.

At first, I thought I was looking for answers. But I don't think I was.

I think I was looking for permission to believe that nothing was wrong with you. Permission to believe there wasn't something wrong with me either.

Because lately your mum and I have noticed a few things.

The baby voice has returned. Sometimes your emotions seem much bigger than they used to. You need one of us close by before you'll try something new. Swimming. Football. Tennis. Ju Jitsu.

It's not that you can't do these things. It's that you seem to need us beside you before you feel safe enough to begin.

And the more I read...

The more I realised these aren't necessarily warning signs. They're often signs of transition. Your whole world is changing. Nursery is ending. School is beginning. Everything familiar is slowly moving beneath your feet. Maybe your baby voice isn't you moving backwards.

Maybe it's your way of telling us, "I’m not feeling ready"

This summer feels more important than ever. A few weeks ago we had no holidays planned. Now we've ended up with three in the calendar. 

Morocco.

Marbella.

Greece.

Three opportunities to slow down before September arrives. Three opportunities to listen a little more carefully. To notice what you're trying to tell us, even when you don't have the words.

Because perhaps confidence isn't something we can build for our children. Confidence grows naturally...

When they know someone will always be waiting beside them.

Not to judge them.

Not to compare them.

Not to ask whether they won.

But simply to remind them they're loved exactly as they are.

So this week I'm breaking the format.

Normally these letters finish with advice. This one finishes with a question.

If you've already walked your child through this transition...

What do you wish someone had told you?

What genuinely helped?

What worried you that turned out not to matter?

How did you help your child find confidence without accidentally placing your own expectations on their shoulders?

I'll read every single reply. Not just for me. But because I know there are thousands of parents quietly standing exactly where Louise and I are today.

Leo...

I don't know what September will bring. I don't know whether Saturday was simply one difficult morning...

Or the beginning of a chapter that asks a little more of both of us. But I do know this. There is no timetable for becoming who you're meant to be. No race to grow up. No expectation that you should move at anybody else's pace. Whatever pace you need...

I'll walk beside you.

Love you always,

Daddy xxx