Starting school is a big milestone. For some children, it’s exciting and full of new adventures. For others, it can feel overwhelming, confusing, and even scary. In our family, I’ve seen all sides of it.

My oldest goes to school with joy.
My youngest loves going to daycare.
But my middle child… his journey has been very different.

From the moment he was little, saying goodbye was hard. Even when he only went to daycare two days a week, it already felt like a struggle. Tears, clinging, and that look in his eyes that tells you he really doesn’t want to be there. And now that he’s old enough for school and goes every day, those feelings have only become more intense.

When going to school feels like a daily battle

Every morning feels like a small battle. Getting dressed, packing his bag, saying goodbye, it all comes with tension. Not because he doesn’t like school, but because letting go is hard for him.

Once he’s there, things usually go okay. His teacher often tells me that he settles in after a while. But she also notices that throughout the day, he’ll sometimes say that he misses me. Luckily, it passes quickly, but it tells me everything I need to know: his heart is still learning how to feel safe without me nearby.

And honestly, that’s hard to watch as a parent.

Seeing your child struggle hurts

It’s difficult when one child runs into school happily, while another holds on tightly and needs reassurance every single day. You start questioning yourself. Am I doing something wrong? Should this be easier by now? Why does this seem so hard for him?

But over time, I’ve learned that every child handles change differently. Some need more time. More reassurance. More predictability. And that doesn’t mean something is wrong, it just means they feel deeply.

The little things that help

What has helped us most are the small, simple rituals.

Every morning, we draw a little heart on his hand and one on mine. I tell him that whenever he misses me, he can look at the heart and remember that I’m thinking of him too. It’s such a small thing, but it gives him comfort and something tangible to hold onto during the day.

Another thing that has really helped is our weekly planning board. Every Sunday, we sit down together and go through the week. We talk about which days he goes to school, what happens after school, and when the weekend is coming. In the evening, we move the arrow to the next day together, so he can visually see what’s coming.

It gives him a sense of control and safety and I’ve noticed it really helps him feel calmer in the mornings.

Slowly, it gets better

I won’t say it’s suddenly easy. It’s not.
But it is getting better.

There are fewer tears. Less resistance. More moments where he walks in a little more confidently than the day before. And I’ve learned to celebrate those small steps instead of focusing on how far we still have to go.

This phase has taught me patience. It has taught me to slow down, to listen, and to trust my child’s pace instead of forcing my own expectations onto him.

A gentle reminder for other parents

If your child struggles with going to school, you’re not alone. And neither is your child.

Some children need more time to feel safe in new situations. Some feel deeply, love deeply, and miss deeply. That doesn’t make them weak, it makes them sensitive and connected.

And sometimes, all they need is a little extra reassurance, a small ritual, and the comfort of knowing that even when you’re not there, you’re never far away.

We’re not there yet, but we’re getting there.
One morning at a time.

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