Why the Jump


I was at a job fair when it actually clicked. Not exactly the setting you picture when someone talks about a life-altering revelation, but that’s where I was standing, so that’s where it happened.

These days I work as an equipment consultant for a company that gets hired out by insurance companies — something gets damaged, they send me out to look at it and make a call: clean it, repair it, write it off. It’s a fine job. Nothing wrong with the company, nothing wrong with the work. It’s just not me, in the way a shirt can technically fit and still feel wrong every time you put it on. I’d been quietly applying elsewhere for months and collecting a tidy stack of silence and “we’re going in a different direction,” which is corporate for “no,” said as gently as possible.

At the fair, I ended up talking to two people pitching an IT training route, sponsored by DAV. I gave them my honest pushback: “Man, I’m 49. I already had a career. I started this one and I don’t love it. I feel like I’m too late to switch again.” They didn’t miss a beat — technology moves so fast, they said, that everybody’s playing catch-up all the time, especially now with AI blowing the doors off everything. Nobody’s “already ahead.” You’re either learning or you’re not. Cheap motivational-poster logic, and it worked on me anyway.

I walked the rest of that job fair and nothing else stuck. So I sat with it. Twenty years in the Coast Guard, and no college degree to show a hiring manager for it — and I’ll admit that one stings. Twenty years of real experience apparently weighs less than a four-year degree and zero experience, on paper, which is a fun thing to learn about the job market at 49. But the more I turned it over, the more I kept landing in the same place: let’s just do it. Let’s jump into IT.

It’s not a decision that came out of nowhere, to be fair. I started college in an MIS program before life rerouted me. During COVID I taught myself a programming language for fun, built a Raspberry Pi cluster in my living room because I wanted to know how clustering actually worked, and messed around in Linux just to break things and fix them again — the classic hobbyist’s cycle of self-inflicted problems. A lot of my friends live in this world, and every time I talk to them about it, something in me lights up in a way the equipment-inspection reports do not.

Is it a questionable decision? Extremely. By the time I finish this program and get my CCNA, I’ll be standing on the doorstep of 50, walking into entry-level rooms next to people half my age with a decade-plus runway ahead of them and, let’s be honest, a head start on the material. I’m doing it anyway, because for the first time in a while, thinking about the work itself feels good instead of just tolerable.

Why networking, and why AI specifically: I don’t actually want to be the guy running cable and racking switches in a server closet — nothing against that work, it’s just not the itch. I want the cloud side, the part where you’re working from a machine that can see the ones and zeros actually moving and trace the whole path a packet takes, not just plug in a box and walk away. And AI is the thing I genuinely can’t put down. I’m reading constantly, building constantly. I’d put myself past the “I know how to type a good prompt into ChatGPT” stage and into actually wanting to understand what’s happening underneath — which, fittingly, is most of why this blog exists in the first place.

…but in all seriousness — here’s the real reason for the blog itself. It isn’t really for an audience. It’s for my kids, and their kids, and whoever comes after them. In my church we take journaling seriously — recording your own history is part of the point, so the people who come after you actually know who you were, not just a name on a family tree. We’re not in the era of somebody finding a leather diary in a drawer anymore. If my grandkids or great-grandkids ever want to know what their grandfather was doing with his one life, they’re going to search for it online. So that’s what this is — a record, kept in public, of a guy who spent twenty years handling hazmat and oil spills deciding, at 49, to start completely over. If anyone else gets something out of following along, great. But first and foremost, this one’s for posterity.

Questionable decision. Full steam ahead.