First Generation Pilot: The Story of the Pilot Life Founder
When I started flying, it wasn’t because I wanted to start a career in the sky — it was because I wanted to have something, anything that I did purely for the joy of it.
Like a lot of pilots, I was always a pretty practical guy. I’ve always been proud of my work, and for a really long time, that was more than enough.
But after a while, I noticed something: working was pretty much all I was doing with my time. When I took to the sky, I was taking back a piece of myself from the corporate grind, and I’ve never looked back.
I’m the founder of Pilot Life, and this is my pilot story.
First to fly
I grew up on a small farm, about two hours outside of Toronto, Canada. It was there, working outside with my family when I was a kid, that I found my first longing for flight.
Just north of our little farm was a gliding club. I could hear the little motors whirring in the air in the distance, and it fascinated me. Once, a hot air balloon even landed in our field.
My mom was (and still is to this day) terribly afraid of flying. Growing up, I became a nervous flyer too, white-knuckling it through many commercial flights.
As a kid, I was fascinated by technology. If something broke, I wanted to take it apart to fix it. I remember saving up for my first computer as a kid, and being so excited when I got it hooked up to the internet.
It never occurred to me to be a pilot, but I always knew that I loved technology, and wanted to be a part of that world, so that’s where my technology career started.
All work, no play
As an adult, my curiosity for technology continued. I went to school for computer programming and began my career in technology.
I loved engineering and building products but frequently found myself crossing over into other disciplines. I interviewed users to learn more about how they used technology, and brought my findings back to product, taking those insights to inform development.
It was invigorating, and without my realizing it, it had become my whole life. The love of my work had become such that any time anyone asked me what was going on in my life, I found myself saying repeatedly, “Well, work is really busy…”
It wasn’t enough for me, and I realized with some chagrin that I had become…boring.
I wanted to be more, a person with hobbies and interests and passions outside of the corporate technology world.
In an act of determination, I went to the flight school on Toronto Island, and I asked them what it would take for me to become a private pilot.
Finding the joy of flight
I was a busy working professional, but I decided I wanted this, to have something that was just for me, and so I made time for it. Early in the mornings before work, I drove across the city for my lessons. I would wrap up, and drive to work promptly after. By 9am, I had already been up in the air flying over downtown Toronto.
If I’m being completely honest, I was pretty nervous in the beginning. Flying excited me, but it also terrified me. On the bigger commercial aircraft, as a passenger, I had never mastered my nerves. I was worried that the same nervousness would carry over into my newfound hobby.
But to my great pleasure, it was a very different feeling being in a smaller aircraft and the pilot yourself. I quickly felt at ease, working alongside my instructor to master these new skills.
I’ll never forget my first solo flight. I was nervous, acutely aware that I was utterly alone in the sky as I began my takeoff. But after a landing that impressed my instructor, I’ll never forget the words from the control tower:
“Congratulations on your first solo!”
Flying as a social activity
Now, my work is freelance, and I share the joy of flight with my family. I’ll never get over the freedom of it — celebrating an anniversary in a new city, seeing my children hold hands on their first time up in the plane with me.
I get so much joy out of this thing, out of the speed and the details and the checklists. But more than anything, what I learned really quickly with flying was that it can be a really lonely hobby.
In the beginning, I didn't know many pilots, and I really wanted to. I wanted to see what other people were flying, the routes they were taking. The only problem was, there wasn’t any one place where pilots could hang out. There wasn’t an easy way for me to connect with other people who shared this incredible hobby.
That’s why I chose to build Pilot Life.
The truth is, it’s not just a digital pilot logbook — it’s a way for people who have this incredible thing in common to connect with people who get it. It’s a way for us all to inspire each other, and to remind ourselves to get out there and make time to fly, no matter how in the way life gets.