
Do Not Ask Why the Old Days Were Better
"Explore why yearning for 'better old days' is unwise. Dive into a generational perspective on change and the inevitable AI revolution."
A response to the AI Parade, from somewhere between the generations
Ecclesiastes 7:10 advises, "Do not say, 'Why were the old days better than these?' For it is not wise to ask such questions."
I've been sitting with that verse a lot lately.
I read a piece this week on Medium by Brittany Chiang called "Welcome to the AI Parade." Brittany is a software engineer who writes with honesty and some grief about watching her craft transformed by AI — from building things by hand to reviewing what the machine produced. She calls herself a glorified TSA agent. She wonders whether her skills are atrophying. She lands in a kind of reluctant acceptance that reads more like resignation than peace.
I don't share her tone. But I recognize the feeling underneath it, and I think she's pointing at something real that most people in knowledge work are still figuring out how to name.
I'm a technologist working in market research. I'm also a writer, an entrepreneur, a father. I've watched AI arrive from several different angles at once — as someone leading a team of technologists working in research, building creative projects and ecommerce ventures, and raising children whose professional lives will be shaped by decisions made right now, by people my age. That's a lot of vantage points. And from all of them, I keep coming back to the same conviction: the best thing we can do when new weapons are developed is for good men and women to pick them up.
Not with recklessness. Not with the naive confidence that the tool will solve everything it promised to. But with intention. With wisdom. With the understanding that the alternative — standing on the sideline mourning what was — serves no one, and certainly doesn't protect the things worth protecting.
The generational split nobody's talking about plainly
Here is what I see when I look at how different generations are processing this moment.
The Boomers are, largely, watching from a comfortable distance. Many are close enough to the end of their careers that AI is something happening to the industry rather than something happening to them. They can observe with curiosity, offer historical context, and step back without the weight of having to live inside it for another thirty years.
GenX — my generation — is where it gets interesting. We're at the pivot. Experienced enough to have built real expertise, young enough to still have a meaningful runway ahead. What I see in my peers is a split: some are using AI aggressively to extend their capabilities, build their exits, and compound their advantages as they approach the back half of their careers. Others are quietly hoping the wave passes before it asks too much of them. The ones who are thriving are the ones who understood early that AI doesn't replace experience — it amplifies it. The judgment built over decades is exactly what makes a seasoned GenXer dangerous with these tools in their hands.
And the Millennials and GenZ have the longest path to walk. They're the ones who have to figure out not just how to use the tools, but how to build careers in an environment where the tools keep changing the rules. The question isn't whether they'll adapt — they will. The question is whether the people ahead of them in line are being good stewards of what matters, or just getting out of the way.
That stewardship piece weighs on me. The handoff is already underway, whether we named it or not.
What I've actually learned
I won't pretend the transition has been clean. AI promised things it hasn't fully delivered. Timelines compressed, but not to the "one week" the headlines suggested. Synthetic tools offered instant insight and gave us useful rough drafts instead. The efficiency gains are real, but so is the human effort required to make quality work out of what the machines produce. Anyone who told you otherwise was selling something.
What I didn't expect is what opened up on the other side of the hard part.
Across my professional work and my creative life, I've found that when AI absorbed enough of the production burden, I had more capacity to be present where presence actually matters. The conversations got deeper. The problems got more interesting. The work I used to consider the "real" work — the craft, the hand-building, the line-by-line construction — turned out to be, in some measure, the scaffolding around the real work. Which was always the thinking. The relationships. The judgment calls nobody teaches you.
I'm not nostalgic for the scaffolding. I'm grateful for what it taught me, and I'm glad I don't have to spend as much time inside it anymore.
The nostalgia I do feel is gentler than Brittany's. I miss the old way the way I miss other things that were good and true and are now behind me — not with grief, but with appreciation. It made me who I am. It doesn't need to be preserved to remain meaningful.
Picking up the weapon
Brittany ends her piece committed to becoming a better TSA agent — to reviewing AI output more rigorously, to teaching her juniors to do the same. That's not wrong. But I'd frame it differently.
The metaphor of the TSA agent is fundamentally defensive. It's about screening, not building. It positions the human as a safeguard against the machine rather than the person who decides what the machine is for.
I think that framing undersells us.
The people who will matter most in this next era — in every field, not just technology or research — are the ones who bring the judgment the tools lack. The ones who know what question to ask before the prompt is written. Who can tell the difference between an output that is technically correct and one that is actually right. Who understand what's at stake in the conversation the data is trying to have. Those things don't come from the model. They come from years of being inside the work, caring about it, getting it wrong and understanding why.
That's what my generation carries. That's what we're responsible for transmitting.
Ecclesiastes understood something the AI conversation often misses: the question of whether things were better before is not just unanswerable — it's the wrong question. What we have now is what we have. The wisdom is in figuring out what to do with it.
Pick up the weapon. Use it well. Teach someone else how.
That's the parade worth joining.
Between Silicon and Soul explores the intersection of technology, human experience, and the questions that live at the edge of both.