The Dream Big Circle

The Dream Big Circle

🩁 Lenny’s Letter -When the end of the holidays brings mixed feelings - for everyone

Sep 04, 2026
∙ Paid

Hello kind grown-up,

The week before school returns is its own particular kind of emotional territory.

For children, it can bring an unsettling mix of feelings that are hard to separate — genuine excitement about seeing friends and returning to routine, sitting right alongside real anxiety about the unknown. A new teacher. A new classroom. A new year with all its uncertainties.

These feelings don’t cancel each other out. They coexist, often uncomfortably, and children don’t always have the language to explain why they feel both eager and afraid at the same time.

For parents and carers, this week often carries its own mix — relief that routine is returning, anxiety about how the children will settle, guilt about feeling relieved, and the logistical weight of the back-to-school preparation on top of everything else.

What helps children in this final week:

Name the mixed feeling without trying to resolve it.
“It makes sense to feel excited and nervous at the same time - both feelings are allowed.” Trying to talk children out of their nerves, or over-emphasising the excitement, can leave them feeling that one of their feelings isn’t valid. Holding both is more honest and more helpful.

Keep the final days gentle and familiar.
This isn’t the week for big new activities or late nights. The nervous system benefits from predictability in the run-up to change. Familiar foods, familiar routines, familiar comfort objects - all of these help regulate a child who is quietly bracing for something new.

Avoid overloading them with reassurance.
Constant “you’ll be absolutely fine, it’ll be great, don’t worry” can paradoxically increase anxiety by signalling that worry is something to be pushed away quickly. A calmer “whatever happens, we’ll work it out together” holds more genuine reassurance.

Let them talk - or not talk.
Some children process best by talking through every worry in detail. Others go quiet before transitions and need companionable silence rather than conversation. Follow your child’s lead rather than your own need to feel like you’ve helped.

Prepare practically where you can.
The uniform laid out. The bag packed. The route to school walked or driven once. Small practical preparations reduce the cognitive load on the morning itself and give children a sense of agency and readiness.

The countdown is always harder than the day itself.

Almost always, the morning of the first day back is better than the Sunday evening before it.

With warmth,
Lenny 🩁


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