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A leadership shadow work coaching prompt for women entrepreneurs — with a real-world example from Brandy, founder of Pine & Shine Co. in Maine. Learn how AI prompts, trauma-informed reflection, and bold visibility created a leadership breakthrough.
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I’ve worked in management.
I’ve run stores.
I’ve worn every hat in a business — except the one labeled “Boss.”
Until now.
When I started my own woman-owned cleaning business in Maine (Pine & Shine), I wasn’t just launching a service. I was stepping into true entrepreneurial leadership — and bringing years of people-pleasing, “support mode,” and fear of being seen along for the ride.
Then I came across a leadership prompt by Sadie Smiley — one that didn’t just ask what I wanted…
It asked what I was afraid to become.
Most leadership coaching focuses on goals.
This one went deeper — to the shadow.
“What’s a leadership trait you admire in others — one you know would help your business grow — but that you hesitate to fully embody yourself?”
My answer?
Bold visibility. Self-promotion. Boss Energy.
Not because I’m not capable. But because I was taught — through trauma, culture, and experience — that it wasn’t safe.
➡️ Read the full raw session here →