The Dream Big Circle

The Dream Big Circle

🩁 Lenny’s Letter - When the holidays look different in every house - and that’s completely okay

Aug 21, 2026
∙ Paid

Hello kind grown-up,

Every September, children return to school and the great informal comparison begins.

Where did you go? What did you do? How was your summer?

For children whose summers looked quieter, simpler, or more ordinary than their friends’, this moment can carry a particular weight - a quiet sense of having had less, done less, been somewhere less exciting.

This feeling doesn’t require an expensive holiday to prevent.

It does require something from us.

What this week is really about:

The pressure around “doing the holidays right” - filling them with activities, days out, experiences worth reporting back - is real, and it falls heavily on parents and carers who are already stretched. The cost of the summer, in time, energy, and money, sits differently in every household.

What children need most from the summer is not adventure.

It is connection. Ease. Unstructured time with the people they love. Permission to be bored and find their way through it. Small ordinary moments that, in the remembering, turn out to have been the best ones.

What helps:

Talk about your own summer warmly and specifically.
Not “we didn’t really do much” - which frames it as a lack - instead “we had fish and chips by the sea and a seagull stole one” - which frames it as a story. Stories are what children carry back to school, not itineraries.

Help your child find their stories.
Ask: “What’s the funniest thing that happened this summer? What was your favourite ordinary day? What will you still remember when you’re older?” These questions help children recognise the value in what they had, rather than measuring it against what they didn’t.

Resist the urge to apologise for a quieter summer.
Children take their cues from us. If we frame the summer as something that didn’t quite measure up, they will absorb that framing. If we speak about it with warmth and specificity, they will too.

Name what was good - genuinely.
Not in a forced, compensatory way. Honestly. “I really loved our day at the coast. That seagull was something else.” Your genuine warmth about ordinary moments teaches your child that ordinary moments are worth cherishing.

The holidays don’t have to be impressive to be enough.

They just have to be yours.

With warmth,
Lenny 🩁


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