When I was a kid, my father would ask me what I wanted to be when I grew up. I never had an answer. That question is hard enough for a teenager, let alone a kid, and it always left me feeling like I had no direction.

At eighteen, I was still stuck in my hometown, working a dead-end computer engraving job, unsure of what path to take.

But when I was eight or nine, I had already felt the spark. I got my first computer, a Commodore 64, and lost myself in games like Zork. Hours would pass until, inevitably, I was eaten by a grue. That love for technology never left me, even when I drifted toward other things in my teens.

Then at twenty, everything changed. I had an accident that cost me part of my left middle finger, and I was out of work for a while. My girlfriend let me borrow her Apple laptop, and I bought a book on HTML. For a month I sat with that machine, teaching myself to build websites. It was simple back then: view source in the browser, download the page, and experiment with the code. Every site I admired became a teacher.

That was the defining moment. It connected the kid playing Zork on a Commodore with the young man trying to escape his small town. Around that time, my girlfriend also gave me On the Road. I devoured it. Between Kerouac’s words and the discovery of HTML, a plan was forming.

One day, afraid of being trapped forever in a dead-end job, I put my feet on the road. Like Kerouac chasing Desolation Angels, I set out into the unknown. I traveled as far as I could: Anchorage to Key West, Los Angeles to San Francisco, Austin to South Lake Tahoe. I made money in coffee shops, working as a barista by day and building websites by night. Without even realizing it, I was living my great American adventure.

After two years, the constant moving wore me down. I stopped in Duck Key, Florida, mile marker 61 in the Florida Keys, and applied for a cashier job in the marina store of a resort. Instead, they sent me upstairs to Room 244 to meet the Director of IT. He sized me up and offered me a job in technology.

On day one, I was thrown into a Citrix migration. I had no idea what Citrix was, or why these thin clients and wires mattered, but I dove in. The whole resort network was still running on cat-3 phone wire tied together with Black Box Network Extenders. Within a few years, I was helping move it all to fiber.

I had left New York, wandered across America, and somehow landed in the Florida Keys, working in tech. Along the way I built websites for the resort too, my side hustle never stopped.

Looking back, I didn’t find Citrix. Citrix found me.