Meet Meighan Cole-Bailey
From Foster Care to CEO™
This is not just my story. It's proof that where you start doesn't determine where you're going.
“I didn't set out to be an entrepreneur. I set out to take care of someone I loved.”
The Beginning
I Didn't Come From Much. But I Came From Enough.
I grew up in the foster care system. I learned resilience before I had a word for it. I learned to keep moving when the ground beneath me shifted — and it shifted often. What I didn't know then was that every hard thing I survived was preparing me for every good thing I was about to build.
In 2010, I purchased my first vehicle to help care for my grandmother. That single act of love became the seed of a transportation company — one that would eventually serve veterans, seniors, children, and individuals with disabilities across multiple communities. I didn't set out to be an entrepreneur. I set out to take care of someone I loved.
Over 15 years, that seed grew into something I never could have imagined: a platform for empowerment, leadership, financial literacy, and legacy. Trucking in High Heels™ was born from that journey — and it exists to help you navigate yours.
Our Mission
To help people navigate life, business, entrepreneurship, financial literacy, and purpose — and become the CEO of their own lives.
Our Vision
A world where every person — regardless of where they started — has access to the tools, knowledge, and community to build income, confidence, and generational legacy.
Forward Movement
Keep going — no matter what.
Leadership
Own your seat at the table.
Legacy
Build something that outlasts you.
Community
Rise together, always.
The Brand Behind the Name
Why? Trucking in High Heels™
People ask me all the time — what does trucking have to do with high heels? I simply say Everything. “Trucking” means moving forward. It means carrying your dreams even when the road gets rough. It means showing up, pressing on, and refusing to stop. The high heels? That's the confidence. The courage. The audacity to show up as yourself — fully, unapologetically — no matter what room you walk into. Together, they mean this: you don't have to change who you are to succeed. You just have to believe in who you're becoming.
20+
Years of Experience
In transportation, entrepreneurship & coaching
6+
Industries Served
From trucking to tech, veterans to youth
100s
Lives Transformed
Through coaching, advising, speaking & mentorship
Nat'l
Stages Across the Country
Keynotes, workshops & corporate training
Ready to Write Your Next Chapter?
Your story isn't over. It's just getting started.
Join the Movement.
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