I've Watched Three Technology Shifts Remake My Career. AI Is the Fourth.

In 1999, I was setting up Windows NT workstations in an office in Minnesota. I had taught myself enough networking to get hired, and I spent my days creating user accounts, running cable, and troubleshooting scanners (we were a document scanning shop). The internet existed, but it wasn't something we used for our jobs. My job was the local network and the high-speed scanners. That was the whole world.

A few years later, the web swallowed everything. The company didn't need someone to maintain a LAN as much as they needed someone who understood how things worked over HTTP. I saw this happening and started reading. Then building. This is when I bought Visual Studio 6.0 Professional Edition, it came in a box. I convinced the shop owner to let me build a web app with it, and after several months and lots of learning, I had a web app which we called iDoc. It allowed our clients to access their scanned documents from anywhere, before this, they could only access their scanned documents by browsing files in a DVD.

Then I moved to Texas with no job and talked my way into a programming role because I could demonstrate that I'd built things on my own. It wasn't easy, I spent a month in Austin, TX living in a motel alone while applying to new jobs daily, spending my entire days looking and submitting new applications, and then failing countless interviews. But about a month later, I got a programming job. That shift from local networks to web applications remade my career completely. Not because I planned it, but because I paid attention, spent time learning it, and built something while the window was open.

The second shift was cloud. I was already a developer by then, working in .NET, writing SQL, building internal tools. When AWS and Azure started making infrastructure something you configured instead of purchased, the economics of building changed overnight. A solo developer could deploy something that used to require a sysadmin, a server room, and a procurement process. I watched entire teams get restructured around this. I also watched individual developers suddenly have leverage they never had before.

The third was mobile. I only built one mobile app (iTranslate), which helped me pay for a new laptop but it quickly got outdated and other apps took over. My time was spent building the APIs and backends that fed these mobile apps. The pattern was the same: a new surface area appeared, the barrier to reaching users dropped, and for a brief window, small teams and solo builders could compete with companies that had hundreds of engineers. Then the platforms matured, the app stores got crowded, and the window narrowed. It didn't close, but the advantage of being early faded.

Each of these shifts had something in common. For a period of time, the tools were new enough that experience mattered less than willingness to learn. The playing field flattened. A solo developer with curiosity could build something real, ship it, and reach people directly. Then, over time, the ecosystem professionalized, the platforms consolidated, and the advantage shifted back toward scale.

I've been through this cycle three times now. And I recognize the pattern because I'm watching it happen again.

AI is the fourth shift, and it's different in a way that matters to me specifically. The previous shifts changed where software ran or how it was delivered. AI is changing what a single person can build. The gap between what I can do alone and what used to require a team has never been smaller.

I use AI tools in my daily work now. I've used them to prototype ideas in hours that would have taken me weeks. I've used them to work through problems in languages and frameworks I don't know well. I've used them to find clarity on large code bases that would have taken years to understand. The speed is real. But speed isn't the part that changed my thinking.

What changed my thinking is scope. A solo developer in 2026 can build, deploy, and maintain software that would have required three or four people in 2018. Not because the developer is better, but because the tools absorbed the work that used to belong to other roles. Design, copywriting, testing, deployment, even parts of product thinking. The leverage is unprecedented, and it's still early.

For someone trying to build independently, trying to build a way out, this is the most favorable environment I've seen in 25 years of watching these shifts. And I don't say that with startup optimism. I say it as someone who has been through the cycle enough times to know that the window doesn't stay open forever.

There's a risk in writing about AI. It invites the breathless hype that makes most AI content unreadable. I'm not interested in that. What I'm interested in is the practical reality: I am a 52-year-old engineer with decades of experience and a finite amount of time outside my day job. AI makes that finite time more productive than it has ever been. That's not hype. That's my Tuesday night.

The previous shifts required me to retool. Learn a new stack. Move to a new city. Start from the bottom of a different ladder. This one doesn't. It amplifies what I already know. My experience with databases, systems architecture, and backend development isn't made obsolete by AI. It's made more valuable, because I can now build on top of it faster and reach further.

I also know from experience that the window has a half-life. The early period of any technology shift is chaotic, full of opportunity, and forgiving of imperfection. The late period is optimized, competitive, and rewards capital over creativity. We're still in the early period for AI. I don't know how long it lasts. But I know I've watched this movie before, and the people who built during the early window are the ones who had something when it closed.

I'm not going to pretend I have a grand AI-powered product in the works. What I have is the recognition that right now, for the first time in my career, the conditions for building independently are better than the conditions for waiting. Every previous shift, I adapted within employment. This time, I also want to use it to build something of my own.

This essay is an example. The stories and observations are mine. I've lived them. But I used AI to help me organize and structure my thoughts. That's the leverage I'm talking about.

Writing isn't the only thing I'm building. But that's a story for a future essay.

That's what this series is about. Not AI. Not technology trends. The question of whether one engineer, late in his career, with real constraints and a real paycheck, can use this particular window to build something that lasts beyond his employment.

The window is open. I've seen enough of them to know what happens next.

This essay is part of an ongoing series. Read all entries →