From Pre-Med to Entrepreneur (After 5 Career Pivots) ft. Chris Gleadall
He was on track for medical school.
Instead, he pivoted...again… and again… and again.
Five different career paths later, he finally built something of his own.
Traveling the world, running his business, and buying gear he never thought he could afford.
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What You’ll Learn:
* How to pivot when you don’t know what you want
* The real cost of staying on the wrong path
* How Chris went from pre-med to running a business
* Why most people stay stuck in careers they don’t want
* How to turn curiosity into something that actually pays $$$$
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About Chris:
Chris Gleadall is an entrepreneur and business owner who walked away from the traditional path and built a career around creativity, autonomy, and ownership.
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Full Context:
This episode is about what it actually looks like to figure your life out in real time.
Chris started on the pre-med track, with a clear path laid out in front of him. But instead of committing, he pivoted—multiple times. Pilot, EMT, creator, and more. Each path taught him something, but none of them fully clicked.
Eventually, that led him to entrepreneurship.
We talk about the pressure to follow a “safe” career, the fear of wasting time, and why most people stay stuck even when they know something isn’t right.
If you’re in your 20s trying to figure out your path—or questioning the one you’re on—this episode will give you a more honest look at what it takes to build something for yourself.
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Find Chris:
Instagram: @lead.shots [https://www.instagram.com/lead.shots/]
Keys Media Studio Website [https://keysmediastudio.com/]
CHAPTERS
00:00 Intro — The Path That Almost Locked Him In
02:10 Growing Up With a “Safe” Career Plan (Pre-Med)
05:30 The Pressure to Stay on the Traditional Path
09:20 Realizing “This Isn’t My Life”
13:10 The Fear of Wasting Years of School
17:40 First Pivot — Trying a Different Direction
21:30 Bouncing Between Career Paths (Pilot, EMT, etc.)
26:50 Why Nothing Felt Right
31:20 Identity Crisis — “Who Am I Actually?”
36:00 Moving to Charleston & Starting Over
40:10 Early Struggles Chasing Something Different
44:30 Turning Curiosity Into Opportunity
48:20 The Shift Into Entrepreneurship
52:10 Making Money for the First Time on His Own
56:00 Why Most People Stay Stuck
59:10 Letting Go of Other People’s Expectations
1:02:00 Final Advice — Choosing Your Own Path