The Dream Big Circle

The Dream Big Circle

🦁 Lenny’s Letter - When disappointment feels big

Mar 06, 2026
∙ Paid

Hello kind grown-up,

Disappointment is often the first emotion we try to soften for children.

We rush to reassure:
“It’s fine.”
“You can do it next time.”

But disappointment has value.

It teaches:

  • effort

  • expectation

  • resilience

When we allow children to feel disappointed — without rescuing them too quickly — we teach them something steady:

Setbacks are survivable.

You might say:

  • “That didn’t go how you hoped.”

  • “That’s disappointing.”

  • “I’m here.”

Then let the feeling move.


✨ Lenny’s letter continues gently for supporters below.

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