Part 1 of 3: The Long Game
This year marks 30 years in the industry. An industry that provided me a challenge, a home, a place to belong, and most importantly, a place to provide for my family. I’ve been working on an immensely personal project lately, but still engaging and watching as our industry takes another large shift. After some thought, some prayer, and honestly some suppression of feelings, I wanted to put some things on paper. Deeply personal, honest, and authentic words that express my optimism for the future through the lens of the past.
This is the first of three pieces. This one is about how I got here.
Technology, and more specifically the art of programming, was a not-so-soft landing spot for me when I was younger. My dream from my youngest memories was to play professional golf. It was all I worked towards. Everything.
I was this interesting mixture of an overly analytical child who rode the short bus, spent several days a month offsite with the “different” children, and possessed the rare — back then — talent of hitting a white ball long and straight. I was also pretty athletic, so while I played every sport, I also did well in school. When I paid attention.
The short bus and the fairway taught me something that took me years to articulate: friendship and capability know no shape or size. The kids I rode with weren’t less than. The kids I competed against on the course weren’t more than. And the analytical brain that got me pulled out of class was the same brain that could read a green or calculate a carry distance before I knew what the word “algorithm” meant.
I had no idea that the first business I started at 17 with a friend in the media industry would become my home for most of my life. We were building dynamic applications for this thing called the World Wide Web. And in that work, I was allowed to use my talents learned as an individual achiever from golf paired with my analytical and problem-solving brain.
Quick aside — if you have kids who enjoy solving problems and are self-reliant, you can do worse than to introduce them to golf. There are too many parallels between the sport and life to address here, but it’s a great vehicle for them to develop. Golf is a sport where you alone are responsible for every outcome. No teammate to blame. No ref to question. Just you, the ball, and whatever you brought with you that day. That shapes you in ways that show up decades later in a conference room or on a late-night deploy.
Fast forward a few years and a devastating wrist injury ruined my hopes of playing professional golf. At the time it felt like the end of something. Looking back, it was the beginning of everything else. The love for computing and programming in particular had started to blossom through my work with Perl, C, and this thing called Linux. I began to really pour myself into my new craft. (That craft eventually led me to Rust and Serverless, but that’s a story for another day.)
Back then, information was consumed from books. I spent hundreds of dollars on texts from physical bookstores. I can remember visiting the library and grabbing anything I could find to expand my knowledge. There was no Stack Overflow. No YouTube tutorial. No AI assistant. You bought an O’Reilly book with an animal on the cover, and you read it until the spine cracked.
The first five years post-college were rough. I want to write that plainly because I think it’s important for anyone launching into this industry right now to hear it.
I launched during the dot-com bubble burst. My first jobs post-college were landscaping, COBOL, and writing reports on a mainframe. I had some experience on the mainframe from an internship helping with the Y2K non-problem. But the web work I loved? Nobody was hiring for it. The market had cratered.
However, I continued to invest. I acquired more knowledge. I met more peers. More friends. I found mentors. Mentors who instilled things in me that helped shape me into the problem-solving and fearless consultant who is willing to take on any task. The kind of person who walks into a room and asks, “where can I add value?”
I want to pause on those mentors for a moment because I don’t think we talk about this enough. These weren’t people who sat me down for formal sessions or followed some leadership playbook. They were people who let me watch them work. People who answered my questions without making me feel stupid for asking. People who, when I made a mistake, helped me understand what happened instead of just showing me the door. Every person reading this either has had someone like that or needs to find one. And if you’re far enough along in your career, you need to be one.
Things were rough but they were good. I moved 5 times in 5 years. Partly because I was adventurous, but mostly out of requirement. Monroe. San Antonio. Chicago. Atlanta. Nashville. Each city came with a new stack, a new team, a new set of problems. I didn’t know it at the time, but I was building something more valuable than any single technical skill.
I learned so much during that span. Looking back, it was intense. I was growing daily. I was adding to my skills. But more importantly, I was learning about myself. I was learning how I handled pressure, ambiguity, failure, and the occasional win. I studied which people on my teams climbed ladders. Which people were trusted advisors. And which people were shown the door. Trust me when I say this — those patterns play out over and over in your career. The people who get shown the door at 25 often get shown the door at 45 for the same reasons. And the people who become trusted? They were doing the same things at every stop.
If I could throw one of those Hollywood cheats like “10 Years Later” on the bottom of your screen I would. Not because 2005 through 2015 weren’t great years — they were. I got married. Both my kids were born. My role with work changed. My role with coding changed. My life and perspective changed. But the foundation was set. The analytical kid from the short bus, the golfer who lost his swing, the guy who moved five times chasing work — he had become someone. Not famous. Not wealthy. But capable, resilient, and clear on what he brought to the table.
That clarity is what made everything that came next possible.