I want to tell you about the moment everything changed.
Not the park bench in Gillette, Wyoming — though that’s where the seed was planted, in the summer of 2023, on an exhausting road trip home from Montana that turned into something I didn’t expect. If you haven’t read that story, you can find it here. What I want to talk about today came after — the moment I sat down at my computer, typed a long and complicated question into a program called ChatGPT, and waited.
What came back stunned me.
Pages of response. Well-researched, well-written, coherent, arrived in roughly thirty seconds. I sat there staring at the screen, genuinely dumbfounded. Not impressed the way you’re impressed by a good movie. Dumbfounded the way you are when something fundamental shifts and you know, in your bones, that the world just changed.
I was in my late seventies. And I had just been handed the tools to compete with the big boys.
The Door That Opened
I had created my ChatGPT account in January of 2023, months before Montana. In those early months I was mostly experimenting — getting recipes, drafting emails, poking around the edges of something I sensed was powerful but didn’t yet know how to use. I was like a man who’d been handed a key without knowing which door it opened.
Montana gave me the door.
When I came home — after the return drive, after Bonnie and I both tested positive for COVID, after the fatigue and the uncertainty and the lingering question of what now — I went back to ChatGPT with something different. Not a recipe. A real question. A complicated, multi-layered prompt about what a man in his late seventies, with a journalism background and decades of real-world experience, might actually be able to build online.
The response changed my life.
What I understood in that moment was not just that AI was powerful — I’d sensed that much in January. What I understood was that it leveled the playing field. That a seventy-eight-year-old man in Tulsa, Oklahoma, without a tech background or a venture capital check, could now access the same quality of research, writing assistance, and strategic thinking as anyone. The gatekeepers were gone. The barriers I had assumed were permanent turned out to be made of paper.
I had found my door. And it opened onto The Encore Project.
The gatekeepers were gone. The barriers I had assumed were permanent turned out to be made of paper.
What the Skeptic Gets Wrong
I know what some of you are thinking. Because I thought it too.
This is for younger people. I’m not technical. I wouldn’t even know where to start. My generation didn’t grow up with this. It’s too late.
I want to push back on every one of those thoughts — not with cheerful reassurance, but with something more useful: the truth.
The research on aging and cognitive engagement is unambiguous. Learning complex new skills is not merely stimulating — it is a legitimate medical intervention for the aging brain. Mastering a difficult task is one of the most effective known strategies for preventing cognitive decline. The brain, it turns out, does not stop responding to challenge because the calendar says it should.
And here is what the skeptic gets specifically wrong about AI: it does not require technical skill. It requires curiosity. The ability to ask a good question — which is precisely what a lifetime of experience equips you to do better than any twenty-five-year-old in a startup. Your decades of hard-won judgment, your nuanced understanding of how people actually work, your ability to spot what matters and what doesn’t — these are not liabilities in the age of AI. They are advantages.
The playing field has not just leveled. For men like us, it may have tilted in our favor.
If you want to explore the tools themselves, our Tech Savvy Seniors category is a good place to start.
What Is Actually Within Your Reach
Write the book
Start the business
If you have a business idea that never found the right moment — a consulting practice built on your professional expertise, a platform serving a community you understand better than anyone, a product born from decades of specialized knowledge — the barrier to entry has never been lower. A recent AARP study found that older adults are rapidly closing the AI skills gap with younger people, and that established businesses run by owners over 55 outlast those run by owners aged 25 to 34 at a rate of three to one. Experience, it turns out, is not a handicap. It is the edge. The Encore Project would not exist without AI. I know that with certainty.
Leave a legacy
Create anyway
The door is open. The only question is whether you will walk through it.
What Growth Actually Looks Like at Seventy-Eight
I want to be honest about something, because I think it matters for anyone standing at a similar threshold.
I did not experience some grand, cinematic transformation. There was no lightning bolt. The bench in Gillette was quiet and ordinary. The ChatGPT response that dumbfounded me was just text on a screen. What happened was more gradual and more real than transformation: it was a decision, made in pieces, to say yes instead of no.
Yes to learning something I didn’t understand. Yes to looking foolish in the process. Yes to building something with no guarantee it would work, at an age when most people would have called it finished. Yes to the terrifying, exhilarating possibility that this chapter might be the most meaningful one yet.
That is what personal growth looks like at seventy-eight. Not a mountaintop. A decision. Renewed daily.
The researchers call this second adulthood — the years after career, after the structures that once defined us, after the world stops asking for our labor in obvious ways. They have found consistently that men who engage with genuinely difficult, challenging work in this season report better mental health, sharper cognition, and a deeper sense of purpose than those who settle into comfortable passivity. A perpetually laid-back existence, it turns out, is not the reward it sounds like. The men who fare best are not the ones who rest. They are the ones who build.
It was a decision, made in pieces, to say yes instead of no. That is what personal growth looks like at seventy-eight. Not a mountaintop. A decision. Renewed daily.
What I Want You to Take From This
If you are somewhere in the middle of your own what now — retired or nearly so, uncertain what comes next, sensing that there is still something in you worth building — I want to say something directly.
The tools exist. Right now, today, the barriers that once separated the amateur from the professional, the small operator from the large institution, the older man from the younger one, are lower than they have ever been in history. AI did not create opportunity out of nothing. But it has made opportunity more accessible than at any point in my lifetime.
The tools exist. Right now, today, the barriers that once separated the amateur from the professional, the small operator from the large institution, the older man from the younger one, are lower than they have ever been in history. AI did not create opportunity out of nothing. But it has made opportunity more accessible than at any point in my lifetime.
You do not need a technology background. You do not need to be young. You do not need certainty about where it leads. You do not need to know, when you sit down for the first time, what the answer will be.
You need a question worth asking. And the willingness to be dumbfounded by the answer.
I was in my late seventies, exhausted from a road trip, recovering from COVID, staring at a screen in Tulsa, Oklahoma. I typed a question I wasn’t sure how to finish. And everything changed.
That is available to you too.
