He could sell anything to anyone. Then technology changed — and he couldn’t adapt. I watched it break him. Students today don’t have to let history repeat itself.
I can still hear my grandfather’s laugh when I close my eyes.
It was the kind of laugh that shook the whole room — big and infectious and completely his own. Maybe that’s just the way memory works when you’re a small child and someone is larger than life to you. But to me, he was everything. The stories he told. The way he could make a room full of people feel like they were the most important people in the world. The way he made you believe every single word he said.
He was a born salesman. From running his own restaurant to eventually finding his way into the car business, my mom used to joke that he could sell ice to an Eskimo. Cliché, sure. But with my grandfather, it wasn’t a cliché. It was just the truth. He had a gift — the kind that can’t be taught, the kind that lives in a person’s bones.
He also convinced me, as a small child, that the house next door was occupied by witches. There had been a fire there once, and that was his colorful explanation for what happened. I believed him completely. I still go out of my way to avoid that house — even now, knowing full well he was, as they say, full of the Blarney. That was the power he had over people. You just believed him.
That’s when everything changed. The technology shifted. The industry transformed around him. And my grandfather — this man who could walk into any room and own it, who could close any deal, who had never met a person he couldn’t win over — found himself unable or unwilling to adapt. The old school salesman and the new world didn’t speak the same language. And at the end of his career, that gap became too wide to cross.
I remember watching that break him in ways I was too young to fully understand at the time. The confidence, the swagger, the absolute certainty that he belonged in any room he walked into — all of it quietly eroded. Not because he had lost his gift. But because the world had moved on without him, and he hadn’t moved with it.
AI is doing to this generation what computers did to his
I think about my grandfather a lot these days. Because what happened to him at the end of his career — that technological revolution that pushed skilled, talented, hardworking people out of industries they had built their lives around — is happening again. Only faster. And bigger.
Artificial intelligence is changing everything. The work landscape that today’s students are preparing for looks almost nothing like the one that existed when they started high school. Jobs that seemed stable are being automated. Industries are being restructured around tools that didn’t exist five years ago. And the students sitting across from me in my office — the ones trying to figure out what to study, what to pursue, what kind of future to build — are making decisions without a clear picture of what that future is actually going to look like.
That scares me. Not because AI is something to fear — I don’t think it is. But because the students who don’t understand what’s coming, who don’t learn to work with these tools and think about how they apply to their field, risk ending up exactly where my grandfather ended up. Left behind by something they never saw coming.
This generation has something my grandfather never did
Here’s what I wish I could have told my grandfather. Here’s what I want every student reading this to understand.
The technological revolution happening right now is not something that’s going to happen to you someday. It’s happening right now, while you’re still in school, while you still have time to get ahead of it. And that changes everything.
My grandfather was in his sixties when the industry transformed around him. He had built a career around a specific set of skills, a specific way of doing things, and he didn’t have the runway to reinvent himself. You do. You have years. You have the awareness that he never had — because nobody was warning him. And you have the ability, if you choose to use it, to become part of the generation that doesn’t just survive this shift but actually shapes it.
The students who understand AI — who learn to use it, who think critically about where it applies and where it doesn’t, who build careers around human skills that technology can’t replicate — those students are going to be in extraordinary demand. Not because they’re smarter than everyone else. Because they were paying attention when it mattered.
Five things every student should be thinking about
AI is extraordinary at pattern recognition, data processing, and repetitive tasks. It is not good at genuine human connection, creative judgment, ethical reasoning, or leadership. Know the difference. Build toward the things it can’t replicate.
The students who will thrive aren’t the ones who resist AI or the ones who outsource everything to it. They’re the ones who learn to work alongside it intelligently — using it to go further, faster, while keeping their own judgment at the wheel.
Critical thinking. Communication. Adaptability. Problem-solving. These are the skills that have survived every technological shift in history and will survive this one too. They don’t become obsolete. Double down on them.
Some fields are going to be transformed by AI faster than others. That doesn’t mean you shouldn’t pursue your passion — but go in with a realistic understanding of how your field is changing and what skills will matter most in it five years from now.
My grandfather was afraid of what was coming. That fear kept him from engaging with them until it was too late. Fear of what’s coming is understandable. Letting that fear stop you from preparing is the only real mistake.
My grandfather was one of the most gifted people I have ever known. His laugh still lives in me somewhere. And if I could go back and give him one thing — one gift — it wouldn’t be a different career or a different era. It would be the awareness, early enough, that the world was shifting. And the confidence to shift with it.
You have that awareness right now. You have the time. You have the ability to become part of a generation that doesn’t just survive what’s coming — but changes the world because of it.
Don’t waste it.
Carpe diem.
Want to help your student build an application — and a future — around who they actually are? Entering the Arena gives you the full strategy for navigating what’s ahead.
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