Confession of a Gen Xer
Where I learn from my daughter what I never thought to ask, and why progress doesn't always mean better
A few months ago, I was out with my wife and daughters in Deep Cove, a picturesque seaside village in North Vancouver with a pier, cute little shops, a theatre and restaurants. We picked up some fabulous doughnuts from Honey’s and sat down on a park bench to feast on their chocolatey goodness under the sunny sky. I snapped a picture of my wife and daughters to capture the moment. A day or so later I uploaded the photo to ChatGPT and created a Pixar-inspired version of the pic and shared it with my wife and daughters on our family group chat. I expected a heart emoji or a thumbs up, but what I got instead was one of my daughters asking me not to upload her picture to AI anymore.
Of course, I felt badly that I hadn’t sought her permission first. The thought hadn’t occurred to me that she would object. It made me pause to think about our differing attitudes toward AI and her concerns about it. Was I naive to be so trusting? Why did I not think much of it? Was it something about my generation?
That moment stuck with me. Here I am, someone who writes about AI transformation, teaches about its implications, and considers myself thoughtful about technology, yet I’d missed something fundamental my daughter instinctively understood. She saw the need for boundaries where I saw possibilities. She asked questions when I hadn’t. Maybe that’s the difference: my generation grew up watching tech arrive with promise; hers inherited it as a fact, complete with a real, messy history. We celebrated each innovation as progress. They’re left calculating the real cost to their future.
If this sounds interesting to you, read on…
This substack, LawDroid Manifesto, is here to keep you in the loop about the intersection of AI and the law. Please share this article with your friends and colleagues and remember to tell me what you think in the comments below.
I remember when my 4th grade teacher, Mrs. Knox, wheeled a TV cart into the classroom. It was a big day. I and my fellow students leaned forward at our desks as the space shuttle Columbia rocketed into the sky, watching with excitement and wonder. It felt like the beginning of something different than our parents’ experience or any generation before us: a brave, new future of possibilities.
As I grew up, I regularly passed signposts of the future becoming real. I loved to hang out at Scooters after class, eat a slice of pizza and play arcade games like Galaga and Stargate. The Atari 2600 video game system brought the fun of arcade games home. The Apple II personal computer made word processing a thing. I learned to code in BASIC and create my own computer programs and share them with friends.
Movies and television shows mirrored what seemed like inevitable progress. Star Wars presented a future that felt lived-in and real, but hopeful— technology was important, but even moreso the Force: the balance of light and dark, dignity and humanity. Star Trek took this a step further, imagining a world in which curiosity and exploration, not profit, motivated its characters and their actions.
Growing up Generation X meant absorbing that message without much friction. We were the bridge between the digital and analog worlds during our childhood and formative years. Newer meant better. Faster meant progress. We didn’t spend a lot of time asking who got to define either one. That outlook helped its adoption.
Then, the internet unlocked the exploration of the world’s information in a way not possible with books and a library card. Keeping in touch with friends became frictionless with email, messaging and online communities. You could spark a conversation with people around the world you never would have encountered.
But the same curiosity that opened doors also kept me from seeing what was on the other side. I treated platforms like Facebook and Google as public commons rather than businesses. They played into this perception with mottos like “Don’t be evil” and offering their products for free. I treated “free” as a gift, not a trade.
I told myself that scale and good intentions were enough. When online misinformation bent public life, I rationalized it as a content problem instead of a structural one (a feature not a bug). When AI began to reshape work and art and the way we find truth, I told myself it was just another tool and left it at that.
Younger generations have seen things more clearly because they have been dealing with the real world consequences.
They pointed to the digital fingerprints we leave behind and the way they get sold. They showed how attention gets gamed and how that gaming changes our politics, our classrooms, and our friendships. They ask for real choices and real consent. Too often, those of us with more power (more votes, more seniority, more money), didn’t prioritize those demands.
I accepted progress as a default and believed the arc of progress bent toward the good. But, I have to confess that its reality hasn’t always borne out that way.
This is an apology for that. I’m sorry I confused convenience with wisdom. I’m sorry I mistook early wins for lasting safety. I’m sorry I called skepticism “cynicism” because I thought it would slow down the steady march toward enlightenment. I’m sorry we let companies write the first draft of a new social contract when we could have insisted on better rules sooner. We didn’t.
I’m not a newborn Luddite, renouncing technology. I grew up with it. I still like what good tools make possible. What I’m renouncing is the reflex to trust the machine before I listen to the people affected by it.
That’s the change I owe them, and that we owe each other, and it’s the change I’m trying to practice.
I have become more critical and questioning of AI because I cannot deny what I see with my own eyes: mass layoffs due to AI efficiency, AI-first policies that put human workers in the back seat, and students’ fear of not having a place in the workforce.
Now, before I adopt new tech, I ask who benefits and who pays. If the value depends on hoarding data, I step back. If the “feature” replaces a human choice with a black box, I want an alternative that keeps a person in the loop. I support rules that put consent and data minimization in writing, with consequences when companies ignore them. I want audits to be normal, not a crisis response. When AI tools learn from human work, I want credit, choice, and fair compensation built in from the start. And when decisions are being made about standards and safety, I want younger voices in the room as a matter of course, not as a strategic photo op.
I will also vote with all of this in mind. Policy won’t fix everything, but it sets the floor. If AI is going to be the new infrastructure (and it is), then it deserves the same kind of maintenance and oversight we expect from bridges, water and electrical systems. Accountability is key. We should plan for failure modes, not be surprised by them.
My generation grew up with a kind of earnest optimism. We saw rockets fly, networks spark, and possibilities expand. That history isn’t the problem. The problem is what we missed while we celebrated, and who carries the burden for our shortsightedness.
To those coming after us: you are right to push back. Keep pushing. Don’t trade away your privacy for “personalization,” your agency for convenience, your intelligence for easy options. Don’t accept a tool that can’t explain itself when the stakes are high. Don’t let anyone tell you that guardrails are the enemy of innovation. They are how innovation earns trust.
Don’t get me wrong, I still like the feeling of a new device out of the box. I still enjoy the first hour with a new electronic toy. But I’m learning to add in a pause, the kind where I read the terms, and ask myself whether this helps or hurts the people who will inherit the world we’re making.
Nothing dramatic, just a little postmodern common sense.
I still have that Pixar-style photo of my family on my phone. But, when I look at it, it’s not the cute cartoon that I think of; it’s a reminder to do better, and be mindful of the better future we owe those we care most about.



