A Legend in My Own Mind
A legend in my own mind is probably the best way to describe it.
I’ve always thought differently from most people.
I was born in Edmonton, Alberta, and raised in the early ’80s—back when life was simple. We rode our bikes, played outside until dark, and didn’t have the internet or cell phones dictating every waking moment. Canada was all I knew… until travel cracked my world wide open.
My first real taste of travel came in my early teens: Southern California, Las Vegas, and Mexico. I still remember falling asleep under the Christmas tree, clutching my paper airline ticket, reading it hundreds of times as it might disappear. Real paper tickets—carbon copies for every leg of the trip. Wild.
Just like today, I told anyone who would listen (most didn’t, and still don’t) that I was going to California, Las Vegas, and Acapulco. Some things never change. We drove all over Southern California, into Vegas, then flew to Acapulco. Those memories are permanently engraved in my mind.
What I couldn’t imagine back then was that I’d later live in Southern California and Las Vegas—and now spend part of my time between Rocky Point, Mexico, and Mesa, Arizona, when I’m not traveling. Looking back, I clearly had a plan—even if I didn’t consciously know it at the time. No matter what happened along the way, I was going to follow it.
The makings of a solo traveler.
After high school in Edmonton and a few false starts, my first real break came when I enrolled in Telecommunications at NAIT. It took me three years to complete a two-year diploma—largely because I wasn’t exactly a model student and my favorite bar, Ezzies, was just across the field.
A week before graduating in December 1995, I interviewed with Northern Telecom, Canada’s largest company at the time. Considering I was in the bottom half of my class, it was a miracle. Somehow, I crushed the interview.
Overnight, I went from making $5.50 an hour to $13.80. Life was good.
I relocated to Calgary in January 1996. Within a couple of years, I was traveling regularly to the company’s Richardson, Texas headquarters. I was boarding planes in freezing Calgary and stepping off three hours later in shorts. I was falling hard for the American dream.
Then I met a flight attendant—another sign of things to come.
Eventually, I was offered a job in Texas, given a work visa, and started traveling full-time. Work had me crisscrossing the U.S. and eventually traveling internationally. My girlfriend followed along and could fly me anywhere, anytime.
Holy shit—my dreams were happening.
That relationship didn’t last, but I still thank her to this day (especially when I jokingly ask for free flights). She’s built a great life raising twin boys, and I’m genuinely happy for her.
Those years permanently warped my brain. I became a travel junkie—unable to stay put, always chasing the next deal. I was turning into North American Darrell.
My next chapter came after 18 years at Northern Telecom, when I landed a job at PayPal. Great company, brutal call-center role. I learned a lot about money management—mostly by dealing with people who didn’t have any. I could have moved up, but I didn’t have the piss and vinegar left. I already had health insurance, investments, and one eye firmly on my Freedom50 travel dream.
Then it happened again.
Laid off.
Northern Telecom in 2014.
PayPal in 2024.
Twenty-five-plus years of service—gone.
There I was in 2024: 52, single AF, unemployed, but financially stable enough to travel whenever and wherever I wanted. I started looking back at my life choices.
Almost everyone I knew had followed the script: marriage, kids, grandkids, 9–5 jobs, one-week vacations, summers at the lake. There’s nothing wrong with that life—but it was never mine.
Statistically, men die at around 73. That leaves maybe 5–10 years of retirement if you’re lucky and healthy. I watched coworkers grind their whole lives only to barely enjoy the end. I lost family members far too young.
Should I have kept my houses in Edmonton, Atlanta, and Charlotte?
My first Edmonton house was 2,400 square feet, custom-built, and mortgage-free. I didn’t even use one of the three bathrooms before selling it. Who walks away from that?
I could’ve settled in Calgary, Dallas, Southern California… or one of the many places I lived temporarily—Las Vegas, Austin, San Antonio, Mexico City, Acapulco, even Brazil. Corporate condos, friendships, relationships, opportunities. Sometimes I wonder if life is just a mirage we interpret the way we want as we get older.
Instead, I chose something different.
In 2015, I settled into a small, turnkey, mortgage-free condo in Arizona, which I Airbnb and use as a home base along with my studio apartment in Rocky Point, Mexico
This is my second attempt at blogging about a life shaped by travel, work, and personal. This time, I’m doing it right. I want to share what I’ve learned about slow travel, inexpensive living, and geoarbitrage—living well while spending less by choosing where and how you live.
Slow travel is about staying longer, living like a local, and letting your dollar go further.
Welcome to my crazy travel blogging dream:
and
www.YouTube.com/@NorthAmericanDarrell
LFG! 