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Defying Expectations: From High School Rebel to Digital Nomad

How a Teacher’s Challenge Ignited My Journey to Entrepreneurial Freedom

Lee Drozak
2 min readJan 25, 2024
journey through life, one womans story
Image created using Dall-E

I was a bit of a smart-ass in high school. I pushed against the rules because I didn’t get why they were there. I wasn’t being rude, just testing limits.

While talking with my history teacher about jobs and our future, things got a bit crazy. I don’t recall all the details, but it ended with a strange exchange.

“He thought he had me pegged and won the discussion with ‘You’ll only be a truck driver.’

Not even close, the debate queen in me came out.

While it was meant to be a dig, I knew that (1) OTR truckers made decent money and (2) traveled to many places. My goal in high school was to earn a decent income so I could wander freely.

I remember how that talk ended with me getting kicked out of class. I was an unruly teenage girl who didn’t follow traditional female roles.

That was the seed that planted the entrepreneurial spirit and having an unconventional life.

That seed started my journey towards living a life different from the usual, unconventional if you will.

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Lee Drozak
Lee Drozak

Written by Lee Drozak

They say life begins at 40, but I’m proof it gets even better at 60—because thriving doesn’t have an age limit, and neither does dreaming big.

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