The Dream Big Circle

The Dream Big Circle

🩁 Lenny’s Letter - Helping children own their summer stories before September arrives

Aug 28, 2026
∙ Paid

Hello kind grown-up,

September is almost here - and with it comes the great informal comparison of summers.

At the school gate, in the classroom, on the first day back: where did you go, what did you do, how was your holiday?

For children whose summers looked quieter, closer to home, or simply different from their friends’, this moment can carry weight - a subtle sense that theirs wasn’t quite enough.

But here is what I want to offer you this week, before September arrives:

Your child already has stories.

They may not recognise them as such yet - because stories that feel small and ordinary to the child living them can seem less impressive than the curated highlights of someone else’s summer. But they are there.

The moment that made everyone laugh. The thing that went unexpectedly wrong and became the best part. The quiet evening that felt, without anyone planning it, completely perfect.

Our job this week is to help our children find and name those stories - so they walk into September already knowing what they have to tell, rather than measuring their summer against everyone else’s.

How to help:

Ask specific questions, not general ones.
“What was the funniest thing that happened?” gets a better answer than “did you have a good summer?”

Try:
“What’s something that surprised you this summer?”
“What’s the moment you’ll still remember when you’re much older?”
“What’s the best thing that happened that wasn’t even planned?”

Treat their stories as stories, not summaries.
When a child tells you something that happened, ask follow-up questions - “what happened next?” and “how did that feel?” - rather than moving on quickly. This teaches them that their experiences are worth dwelling on.

Share your own summer story warmly.
Not the highlights. The actual story - the thing that went wrong and became funny, the quiet moment that felt unexpectedly good, the small thing you’ll remember. Model what a good story looks like, and that ordinary life produces them all the time.

Let them practise telling it.
Children who have told their story out loud once are far more confident telling it again. Give them the audience before September does.

Your child’s summer was enough.

Help them know it - before the comparison begins.

With warmth,
Lenny 🩁


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