How IT Pros Learned Then vs. Now and Why It Matters for the Future
From books to boards to robots, how professionals have always adapted...
TL;DR
IT pros used to learn by breaking things, fixing them, and actually understanding how stuff worked. Now? AI, Google, and instant answers. Fast, but shallow. If you don’t know why something works, you’re pasting fixes, not solving problems. Modern tools are great, but real expertise still matters.
The Shifting Landscape of IT Knowledge
Learning IT used to be a grind.
You had to break things, fix them, and break them again just to understand how they worked. No instant answers, no AI-generated solutions, just you, a manual, and hours of frustration.
But now everything is different.
AI, Google, and endless online resources have changed the way we learn and absorb (or not) information.
The journey of IT professionals has transformed from hands-on tinkering to leveraging AI-driven tools as a wedge. This evolution raises a question:
Has this shift made IT pros wiser, or merely quicker at finding answers?
Breaking Things: The Original IT Bootcamp
Let me paint you a picture of old-school IT learning: It's 2AM, you're surrounded by Cisco manuals that could double as doorstops, squinting at a PuTTY terminal while questioning your life choices. Why? Because you fat-fingered ONE configuration setting and lost remote access to the device in a datacenter 6 hours away. Totally didn’t happen to me…nope.
And you know what? Those were the good ol’ days.
I'm not some greybeard reminiscing about punch cards because I’m not THAT old - I cut my teeth building PCs at eight years old, when "tech support" meant praying your computer would POST.
But even in my professional journey through infrastructure and cybersecurity, learning meant one thing: breaking stuff and fixing it yourself. The amount of things I broke after-hours that nobody really knew about in the business is astounding. I work best under pressure anyway.
The old-school IT curriculum looked something like this:
RTFM: Picture yourself decoding technical documents that made tax codes look like light reading. No ChatGPT summarization here - just you, caffeine, and endless pages of protocols.
Forums & Usenet Groups: Where simple questions like "How do I configure BIND?" sparked 47-page flame wars about DNS architecture. But buried in those threads? Pure gold.
Trial & Error: You haven't truly lived until you've accidentally dropped a production database. Ask me how I know.
Mentorship: Learning from battle-scarred veterans who had already made every mistake you were about to make (and invented a few new ones).
This method built a deep, almost instinctive understanding of systems. You didn’t just know the answer, you understood why it worked. That kind of knowledge sticks and is referred to as “wisdom”.
I’m no greybeard in terms of age, but a strong 60% of my learnings and cutting my teeth in infrastructure, security, and operations were through this method. At about eight years old I ventured beyond video games and started to build and repair PCs. These early experiences laid the foundation for a career defined by hands-on problem solving.
Anecdotally, as a kid, my old man used to say “The wisest man is the one who made the most mistakes” a lot. Ironically, I never really saw him make mistakes. Only later in life would I realize that I was doing the EXACT same thing. We both make mistakes, but they are calculated and quickly recovered (mitigated) as a part of the learning process.
This is a stark contrast to today’s learning environment.
The Manufacturing Floor Parallel
This reminds me of something I see constantly in manufacturing environments. Walk into any production facility built before 2010, and you'll find machines running on Windows XP, controlled by proprietary software that hasn't been updated since the Bush administration. These systems keep running because of one 58-year-old maintenance tech who's been there since the equipment was installed. He doesn't have documentation, it's all in his head. The company relies entirely on his tribal knowledge.
And it works! Until it doesn't. Until he retires, or the one replacement part they need is no longer manufactured, or a security vulnerability finally gets exploited (because you totally didn’t air gap the thing).
Then it's all hands on deck, production stops, and suddenly everyone wishes they'd invested in understanding how things actually work rather than just keeping them running. Meanwhile the poor IT person is trying to connect to this machine via 6 adapter dongles daisy-chained together.
We’ve all been there. Those situations build character.
IT knowledge follows the same pattern. You can paste solutions from ChatGPT all day long, but when something truly breaks, you need that deep understanding that only comes from having broken and fixed things yourself.
The Modern IT Classroom: Stack Overflow and Pray
Today's landscape is... different. Why spend hours understanding BGP when you can copy-paste from ChatGPT? Need to configure a firewall? There's probably a TikTok for that. Need a code snippet to customize your ERP? There’s a reddit thread with your exact problem and solution.
Don't get me wrong - I'm not here to yell at clouds. These tools are incredible, but they're creating a generation of IT pros who can follow recipes without understanding the ingredients. It's like being a chef who can only cook by watching YouTube tutorials.
When something hands you the answer without requiring you to understand the underlying mechanics, you risk becoming just an operator instead of an engineer.
The convenience is great until you hit an edge case AI can’t solve.
Learning now looks like:
Google, Stack Overflow, and AI Tools: The answer to almost any problem, just a few keystrokes away.
Interactive Labs & Virtual Sandboxes: Experimenting without the risk of bricking a system.
Low-Code & No-Code Solutions: Making things work without needing to understand how they work.
Video Tutorials & Online Courses: Bite-sized lessons for quick consumption.
It’s convenient. It’s efficient. My issue with it is that many newer IT pros are great at following steps, but not at understanding what’s happening under the hood. If the AI-generated solution doesn’t quite fit? They’re stuck. I predict we’ll see this reverb of issues when solutions don’t follow the happy path and don’t have resiliency built into them.
The Right Balance is AI as a Tool, Not a Crutch
AI isn’t the enemy. It’s a powerful tool if used correctly. It’s just that though…a tool.
The best IT pros I work with know that blending old-school depth with new-school speed is what sets them apart. Relying solely on AI to spit out answers? That’s a recipe for shallow knowledge. Ignoring AI altogether? That’s being stubborn and probably unemployed soon.
The real magic happens when you combine both approaches. Building, breaking, and fixing systems instills a deep-rooted understanding, while AI can handle repetitive tasks, freeing you to tackle more complex challenges.
It's the difference between knowing how to use a tool and understanding how that tool was built. Both have value, but only one will save you when everything's on fire and the standard solutions aren't working.
IT pros who thrive in this era won’t be the ones blindly following AI-generated solutions, nor will they be the ones clinging to outdated ways. They’ll be the ones who embrace efficiency while staying grounded in the fundamentals.
With the changes I’ve mentioned, I STRONGLY encourage you to work on the below skills, as they are abilities that will keep you resilient in the job market and set you apart:
Self-Assessment for IT Leaders
If you’re leading an IT team, ask yourself these questions:
Am I using AI as a tool to learn, or as a shortcut to get things done?
If AI and Google disappeared tomorrow, could I and my team still troubleshoot effectively?
Does my team understand the tech we rely on, or just follow scripts and apply patches?
Am I hiring and training problem-solvers, or just people who know how to Google?
Is IT in my company a strategic function, or just an over-glorified helpdesk?
Fast is good. Smart is better. Build both. If you let one lapse for too long, you’re going to run into situation where your team as no depth of wisdom to them, or the opposite…relying on a single rockstar to carry the weight.
The Future of IT Learning: Blending AI with Human Expertise
The IT field has always been shaped by adaptation and problem-solving. AI is simply the next evolution, but it should not fully replace human expertise. The best IT professionals will be those who:
✅ Use AI to enhance their expertise, not replace it.
✅ Question and validate AI-generated solutions instead of blindly accepting them.
✅ Develop human skills like problem-solving, leadership, situational awareness, and adaptability to stay irreplaceable.
If you're relying purely on AI to solve your problems, you're not an IT professional - you're just a very efficient Googler with admin privileges.
When the robots finally take over, they'll keep around the humans who know how to fix them. Be that human.