October 20th, 2025. I’m at the Go Duck Yourself restaurant in San Francisco with my grandsons, Mason and Lincoln. We’re grabbing dinner before I head to TED AI the next morning—two days of talks about how AI is transforming everything from civilization to culture. Naturally, I’m curious where they stand on all this.
Mason is 19 and works at a bait shop. Lincoln’s 16. They’ve grown up with screens, with technology as background noise. So I expect them to be all in on AI.
That’s not what I get.
Mason looks at me across the table and asks, “How would that help me catch more shrimp or sell more bait?”
He’s not being dismissive. He’s genuinely asking. What does any of this AI stuff have to do with his actual life—hands in water, customers who need the right hook for the right fish?
This isn’t the first time we’ve had a conversation about technology and values. Four years ago, when Mason was still in high school, we’d been working with a company developing a ring you could wear to measure your cognitive load throughout the day. Smart tech—helps you understand when you’re most focused, when you need rest, and how you learn better.
Mason put his fork down. Looked me straight in the eye.
“It’s cheating, Pops.”
Not ineffective. Not unnecessary. Cheating.
I tried reasoning with him. Data. Logic. Productivity arguments. None of it landed. You can’t reason with an emotional reaction, and I was arguing technology while he was defending his moral framework.
Now, at 19, the same grandson, a different angle on the same question. Not “is it cheating” but “what’s the point?”
Both questions come from the same place: a deep sense that achievement means something when it’s earned through actual work that matters.
Mason wasn’t raised to fear technology. He was raised to value integrity, honest work, and earning what you get. So, whether he’s 15 looking at a cognitive enhancement ring or 19 looking at AI for his bait shop, his framework is consistent: Does this help me do real work, or does it just make things artificially easier?
Meanwhile, I’m 72, and I look at AI like it’s just a better hammer.
That disconnect isn’t a bug. That’s the whole story.
I’m a Boomer. Born when computers were science fiction. My kids are Gen X; they didn’t have a computer in the house until they were in high school. Their kids, Mason and Lincoln, grew up with screens, mostly iPads and iPhones. And now Gen Alpha, the youngest generation, they’re the first to grow up with AI as a fact of life.
This isn’t random. There’s a pattern.
Gen X is phobic about integrating new technology. They’re the last of the digital immigrants; they remember life before the internet, before smartphones, before all of this. So when they’re in management positions, making AI adoption policies? They’re making decisions based on their own anxiety.
Gen Z is facile with the tools. They’ve had them since they were babies. But they didn’t have AI until now. And more importantly, they were raised with strong ethical frameworks about earning achievement and maintaining integrity.
Gen Alpha will grow up with AI, just as Gen Z grew up with Google; it’ll simply be a part of the landscape.
And Boomers like me? We’re sitting on the sidelines thinking we’re too old to understand this stuff.
That’s the problem.
Because what we actually have is decades of experience navigating technological upheaval. We learned computers late in life. We built businesses through multiple technology waves. We know something Gen Z desperately needs to know: how to adopt new tools without losing your soul.
However, we’re referring to ourselves as “older” instead of “elder.”
Oscar Wilde said it: “With age comes wisdom, but sometimes age comes alone.”
Most of us are choosing “alone.”
It’s 2016, and I’m in Tampa, Florida. I’m working with Lt. Col. Scott Mann, and he says something that stops me: “I know what you are. You’re a sherpa.”
As soon as he said it, I knew he was right.
Sherpas aren’t tour guides showing people around the easy sights. Sherpas guide people up the hardest mountains. They’ve climbed those peaks before. They know where the dangerous parts are, when to push and when to rest, and what resources you’ll need before you know you need them.
That’s different from a mentor.
After that dinner with Mason and Lincoln, I began exploring what sets elders apart from mentors. Mentors focus on skills and career development. “Here’s how to succeed in this field.” “Here’s the path I took.” “Here are the techniques that worked for me.”
Elders focus on wisdom, values, and navigating uncertainty while staying true to themselves.
In Indigenous traditions—which have contemplated this for a lot longer than we have—elders aren’t defined by age. Their communities recognize them because they’ve earned respect through wisdom, harmony, and balance in their actions and teachings.
The question a mentor asks is “How do I do this job better?”
The question an elder asks is, “How do I stay myself while the world changes around me?”
Mason doesn’t need someone to teach him about AI. The technology is easy for him. What he needs is someone who’s been through enough changes to say: “This is how you evaluate new tools without losing your moral center.”
That’s not a mentor conversation. That’s an elder conversation.
And here’s the thing about elder conversations: you have to question the question.
Every Saturday morning, I do a show with my best friend, Duey Freeman. We call it the Elder Council, and we didn’t plan it that way—it just crept up on us like age does.
We began in association with the Man/Uncivilised movement, which Traver Boehm created. Every week, we’d have some challenge to consider that men were facing. Younger men started asking us questions. Not mentor questions—” how do I get promoted” or “what skills should I develop.”
They were asking elder questions: “How do I stay true to my values while building a career in tech?” “How do I know if I’m making the right choice?” “What’s my purpose here?”
Different questions entirely.
And we realized: we’d called this into being over time. It stuck. For me, and I think for Duey, it’s become how we self-identify.
We’re not mentors. We’re elders.
And here’s what I notice: it takes about thirty minutes of inquiry to get there. To question the question, to discover the real question underneath the question they came in asking.
Someone comes in thinking they want advice about their career. Thirty minutes later, we discover they’re actually wrestling with whether they can maintain their integrity in their industry. The presenting question is never the real question.
You have to question the question.
That’s the elder’s role. Not giving answers. Asking questions that help people discover what they’re actually asking about.
I wish someone had sat me down at 40 and asked me four questions.
The Japanese have a concept called ikigai, which translates to your reason for being. Westerners like to simplify it into four overlapping circles:
* What do you love?
* What are you skilled at?
* What can you get paid for?
* What is your mission?
At 40, I was ten years into my tenure at Wavefront Technologies; two years before the merger, before the company went public, and back when we were still a major player in the computer graphics industry.
If someone had asked me what I loved? Easy. Creating graphics. Being around people who were into animation. Being behind the scenes, I’d been a magician since I was 18, and I’d always loved how magic is done more than the trick itself. Making the tools that visual magicians used got me in the loop. I loved people, travel, and being on stage. Wavefront delivered all of that.
What were my skills? Communication, writing, presenting, demo-ing. Team-building, community-building—I’d built our user group to 5,000 people, larger than anyone in the industry. My primary skill was listening to customers. Spending a day in their shops. Observing, asking questions, and learning how they did what they did with our software.
What could I get paid for? Turns out, “being an ambassador.” I didn’t have a name for it until the merger with Alias, when I was 42.
So at 40, I had three circles perfectly aligned: passion, skills, and market value.
But here’s what I didn’t have: a personal mission beyond the job.
If I’d been asked about my mission at 40, I wouldn’t have had an answer. And nobody asked.
I didn’t discover my mission until I was 57.
My mother-in-law and I were driving home from our first TEDxSantaBarbara. She asked: “Why do you two spend almost 1,000 hours on this project?”
And I heard myself say: “It’s the first true community service I’ve ever done. There’s literally nothing in it for me other than knowing we helped propel ideas into the world that might change lives and inspire change. Full stop.”
That’s when it dawned on me. That feeling has only amplified since.
But what if someone had asked me that question at 40?
What if an elder had sat me down and helped me question the question, helped me discover that I wasn’t asking “how do I succeed in this industry” but really asking “what am I here to contribute beyond making money?”
How would my life have been different if I’d found that fourth circle 17 years earlier?
Right now, navigating AI while maintaining your moral center?
That’s Everest.
Gen X middle managers are at base camp arguing about safety protocols.
Gen Z is staring up at the mountain, asking, “What’s the point of oxygen if I can climb without it?”
And elders who’ve climbed multiple “impossible” mountains, learning computers late in life, building companies, adapting to every technology wave, we’re the sherpas who know where the dangerous parts are, when to push and when to rest, what resources you’ll need before you know you need them.
The sherpa doesn’t carry you up the mountain. The sherpa climbs with you and asks the right questions at the right time:
“What are you trying to protect?” “What’s your mission here?” “Can you maintain your integrity while using this tool?”
Mason isn’t wrong to question AI’s relevance to catching shrimp. That’s beautiful. That’s exactly the grounded thinking we need.
But nobody’s asked him the elder question yet: “What values are you trying to protect, and how do those values help you decide which tools serve your work?”
That’s an entirely different conversation from “AI isn’t cheating, let me show you the data.”
That’s questioning the question.
Most boomers are sitting on the sidelines thinking, “I’m too old to understand this AI stuff.”
I get it. The technology moves fast. The terminology changes. You feel like you’re always catching up.
But what if you’ve been looking at the wrong mountain?
You don’t need to understand every technical detail of AI. Gen Z has that covered. What they don’t have is someone who’s navigated enough technological upheaval to say: “Here’s how you adopt new tools without losing who you are.”
You’ve done that. Multiple times. You learned computers late in life. You built businesses through technology waves. You know something Gen Z needs to know desperately.
So the question isn’t whether you understand AI’s architecture.
The question is: are you willing to be the sherpa on the values mountain while they handle the technical climb?
You had three of the ikigai circles aligned throughout your whole career. Now, in what you think is retirement, you have the chance to discover the fourth: eldership.
Not mentorship—teaching people skills.Eldership, helping people navigate uncertainty while staying themselves.
It’s being actively engaged in solving current problems. It’s being the sherpa on the hardest mountains. It’s asking younger generations the questions that help them discover their mission earlier, so they don’t have to wait until 57 or 72 to figure out what their life is really about.
Here’s the ikigai framework for potential elders:
Ask yourself what you’re passionate about. If three or four things come to mind without effort, you’re not done. You have energy and purpose waiting to be directed.
What about skills? At 65, 70, 72, you have decades of hard-won expertise. Multiple mastery areas. Professional accomplishments. Real-world problem-solving experience.
What skills did you get paid for? You have 40 or 50 years in market doing jobs. You learned things at those places. Things that can’t be Googled or AI-generated because they came from living through it.
And here’s the big one—what is your mission? This is the question that might not have an easy answer. Do you believe you have a purpose or a mission?
If Gen Z is navigating AI adoption without guides, if generational knowledge is draining out of companies through early retirement and layoffs, if younger generations need help maintaining their values while adopting new tools...
Maybe your mission is eldership.
Look, I know what you might be thinking. “Easy for you to say, Mark. You had a tech executive career, TEDx organizing, coaching with a Lt. Col. Not everyone has that foundation.”
You’re right. I’ve been fortunate. But here’s what I learned early, before I had access to any of those people: eldership starts with books, not bank accounts.
When I was younger and couldn’t afford coaches or conferences, I had books. I had the library. I had people who’d written down what they learned. That’s where my early elders came from, authors I never met who asked me questions through their words.
Eldership isn’t about having had the perfect career or the right connections. It’s about having climbed some version of a hard mountain, and every life has hard mountains. Working multiple jobs to support a family? That’s a mountain. Navigating a career with limited resources? That’s a mountain. Raising kids while the world keeps changing? That’s Everest.
The question isn’t whether you’ve had privilege. The question is: have you learned something from the mountains you’ve climbed that could help someone else on their climb?
If yes, you’re qualified for eldership.
The elder’s gift isn’t wisdom.
It’s the ability to question the question.
It’s asking Gen Z: “What values are you protecting?” instead of arguing about whether AI is legitimate.
It’s asking your grandson: “What makes work meaningful to you?” instead of debating the productivity benefits of automation.
It’s asking boomers: “Why are you doing this?” instead of letting them retire into irrelevance.
It’s asking at 40, or 30, or 25: “Do you have all four circles aligned, or are you missing your mission?”
Because it’s not until you’re about halfway through that you figure out what your life is really about. But elders can short-circuit that timeline, not by giving answers, but by asking the questions that trigger the discovery earlier.
I’m going to reach out to Mason and Lincoln and have a deeper version of this conversation. Not to give them answers about AI, career, or purpose. They can’t answer those questions yet, and that’s fine.
But I can plant the seed that the questions exist.
I can normalize the inquiry.
I can help them learn to question the question.
So that when they’re navigating AI adoption, career choices, values conflicts, they have a framework for asking: “What am I really asking here? What question is underneath this question? Does this align with my mission, even if I’m still figuring out what that mission is?”
That’s the elder role.
Not telling younger generations what to do.Asking questions they didn’t know they should be asking.
The hardest mountains need guides who’ve climbed them before.
Gen Z is standing at the base of the AI mountain.Gen X managers are arguing about equipment at base camp.And elders are sitting on the sidelines thinking they’re too old to help.
You’re not too old. You’re exactly what’s needed.
Stop being “older.”Start being “elder.”
The sherpa doesn’t stay at base camp.The sherpa climbs.
EPILOGUE
The morning after I wrote this, I had breakfast with Cameron. He’s 30—right on that Millennial/Gen Z cusp—and I’ve been both mentor and elder to him over the years as he’s planned his World’s Fair project for San Francisco.
I wanted to test the thesis.
We were talking about generational dynamics, and I said something about Gen X being my kids’ age, their early fifties, and I still look at them as kids even though they’re running the show now.
Cameron laughed. “That’s such a boomer thing to say.”
He was right. Caught in the act. Still thinking of 50-year-olds as kids who shouldn’t have the keys to the car.
Cameron’s been planning a World’s Fair in San Francisco for the past few years. He’s navigating city politics, institutional resistance, and generational gatekeeping. And knowing him, he will build it.
He told me about trying to work with the city’s existing institutions and hitting walls everywhere. “I could go in there, but they’re not gonna let me run stuff. They’re like, ‘oh, nice, thanks for coming by.’” His solution? Build entirely new institutions instead of trying to fix the broken ones.
Then he said something that validated everything I’d written:
“I say this often. It’s like, it’s up to me. All of my friends and I have to step up and take responsibility for building the future we want to live in, because no one else is going to do it. The older generation, the Gen X version, everyone’s on their way out the door.”
That disconnect I wrote about between my grandsons and me?
It’s real across the entire generational landscape.
Gen Z and younger Millennials are staring up at mountains they need to climb, asking legitimate questions about tools, values, and what matters. Gen X is managing the fear instead of leading through it. And boomers are sitting on the sidelines thinking they’re too old to help.
When I asked Cameron about Gen X’s irrational fear of technology, he didn’t hesitate: “Totally. Totally. It’s fear of the unknown.”
He doesn’t need me to teach him about technology.
He needs me to help him question the questions he’s asking.
So I’m taking my own advice. Reaching out to Mason and Lincoln. Staying in the game. Being a sherpa, not a spectator.
Because Cameron’s right, it’s up to his generation.
But that doesn’t mean elders should sit on the bench.
The sherpa doesn’t stay at base camp.
The sherpa climbs.
