The Rise of the Keyboard Cowboy

There’s been a shift lately—subtle at first, but now I can’t unsee it.

Like that kid from The Sixth Sense, only it’s not dead people I see. It’s non-technical staff pitching enterprise solutions built on YouTube tutorials and vibes.

It started as curiosity. A question here, a “Hey, how hard would it be to automate…” there. But ever since ChatGPT showed up, it’s become a full-blown epidemic: The rise of the keyboard cowboy.

You know the type. The spreadsheet samurai. The workflow whisperer. The mid-level project manager who once built a macro and now thinks they're a goddamn software architect.

They’ve got a keyboard, a browser, and a vague memory of a Reddit thread—and suddenly they’re galloping straight past the people paid to solve technical problems, convinced they’ve just invented the next enterprise solution.

And the worst part?

They go straight to leadership.

No consult with IT.

No questions about supportability, security, architecture, or compliance.

No reference to existing IT roadmaps.

Just a slick little demo in a meeting, some buzzwords like “automation,” “AI-enhanced,” and “cost-saving initiative,” and boom—they’re a fucking visionary.

Meanwhile, back in the IT stable, we’re left cleaning up whatever Frankenstein’s monster they birthed in a SharePoint list or Access/VBA combo. Because it’s not if it breaks—it’s when. Five of my last ten years in this industry have been spent cleaning up those messes.

Now, instead of keeping an eye on actual industry trends and methodically implementing solutions within our operating environment, I’m stuck entertaining a steady stream of ideas that went up one flagpole, jumped over to ours, and came back down like a flaming hot grenade.

So we wait for the call.

The call we know is coming.

It’s always us.

IT.

Never the cowboy.

They’re off chasing their next big idea—probably prototyping a chatbot that feeds your Outlook calendar to a toaster in their shiny new leadership role.

I don’t go to the mechanic and say: “Yeah, I don’t think you need to jack her up today. Just clear the codes and we’ll be fine.”

I don’t tell my plumber: “PEX is overpriced. I’ve got some galvanized pipe in the garage. Let’s use that—should knock a couple hundred off the job.”

Because that would be insane.

And yet, people waltz into my world—decades of expertise, architecture, and operational complexity—and casually say things like:

“Can’t we just write a script for that?”

“I heard we can build our own ticketing system in Teams.”

“I saw a video where someone used ChatGPT to automate their whole workflow.”

Cool. I saw a video where a guy used a microwave as a hot tub timer. Doesn’t mean I’m putting my defibrillator in a Whirlpool.

This isn’t about gatekeeping. It’s about respecting the work.

Having a computer doesn’t make you IT.

Being adept at purchasing underwear on Amazon doesn’t equate to decades of experience with enterprise solutions.

It just doesn’t.

If you’ve got a good idea? Awesome. Come talk to us. We want to help you build something real. But don’t pitch half-baked nonsense to leadership, rope them in with promises, and dump it on our lap when it breaks.

Start with the problem you’re trying to solve.

Start with the process you’re trying to improve.

Stay out of solution space—that’s what the nerds are for.

That’s why we’re here.

I’m all for innovation.

I’m just not here for cleanup on aisle “you should’ve fucking asked first.”