In 1984, I bought an IBM PC Junior.
I want to be honest about how that sounds, because it sounds like I’m bragging, and maybe I am, a little. But mostly I’m telling you so you understand something about me before I tell you something about my father. I was not a reluctant adopter of technology. I was, by the standards of Tulsa realtors in the 1980s, something close to a wizard. People called me with questions. I laugh about it now — me, the guy other agents phoned when their computer did something they didn’t understand — but at the time it felt completely natural. I love words. A machine that could manipulate them faster than I could blink wasn’t a threat. It was a thrill.
A few years before that, I’d watched a smaller miracle happen in our front office at Mastercraft Professional Contractors, the electrostatic painting company I ran out of a renovated fifty-year-old dry cleaners building in Tulsa. We were proud of that space — natural light, modern cubicles, four workstations with the good padded dividers. My office manager, Bert, had been talking for weeks about something he wanted to bring in. One day he did: a word processor, not much bigger than a typewriter, with a monitor maybe thirteen inches across. It was his, not the company’s. He set it up in his office and gave us all a demonstration.
Everybody said the same thing. Wow, that’s cool.
I remember being skeptical until I actually watched it work — a document appearing clean and fast, no correction fluid, no retyping a whole page because of one mistake — and then something in me just went: okay, I get it. None of us had any idea where it was headed. We just knew we were proud of our fax machine and our multi-line phone system. When it came to technology, we thought we were killing it.
I tell you all of this because I think it’s important context for what I actually want to talk about, which is my father.
From Wonder to Fear
My dad was a decorated fighter pilot in the United States Navy, a war hero who flew combat missions in the Pacific during World War II. He was smart. He was handsome. He made decisions in the air, under fire, that most of us will never have to make about anything in our entire lives. And he died in 2007, at eighty-two years old, having never once used an ATM.
A man who’d flown combat missions, who’d been decorated for valor, who had every reason in the world to trust his own competence — and a beige plastic box with a blinking cursor could make him feel like a child who didn’t know how to tie his shoes.
I tried to help him with technology a handful of times before he died. It never went well. He wanted every single instruction written down — not the broad strokes, not “let’s just get a feel for the basics,” but every tiny step, in order, with nothing skipped. If I tried to move faster, to show him the big picture instead of the granular sequence, he froze. He was terrified of missing something, forgetting something, getting lost in a process he couldn’t see the shape of. It sounded hostile sometimes, when he got like that. You wanted to leave the room. But it wasn’t really hostility. It was fear wearing hostility’s clothes, because admitting the fear plainly would have been worse.
Here’s what I’ve come to believe, watching that happen more than once: my father was terrified of looking foolish. A man who’d flown combat missions, who’d been decorated for valor, who had every reason in the world to trust his own competence — and a beige plastic box with a blinking cursor could make him feel like a child who didn’t know how to tie his shoes. That’s not a small thing. That’s not “old people don’t like computers.” That’s a particular and specific kind of fear, the fear of losing control in front of someone who loves you, and I think it’s more common in men of his generation than we like to admit.
A Different Kind of Brave
I never had that fear. I still don’t entirely understand why. Maybe it’s because words have always felt like home to me, and anything that helped me move faster through words felt like an ally instead of an enemy. Maybe it’s just temperament — I was curious where he was cautious, willing to look foolish for thirty seconds in exchange for getting somewhere new. I don’t say that to make myself sound braver than him. He was braver than I will ever be, in the ways that actually mattered, in an airplane, in a war. This was just a different kind of brave, the kind built out of comfort with not knowing yet, and it happened to be the kind I had plenty of.
So I kept going. Through the decades, through the real estate years, through the Planning Commission years — I was never the man standing in line at the printer wondering how it worked. And then, a few years ago, came the leap that made the IBM PC Junior look like a toy.
AI. ChatGPT, in the beginning.
I was trying to solve the first crucial, overwhelming problem of building The Encore Project — how do you actually construct a plan for a platform like this, from nothing, as one man with an idea and no staff? I remember the day, though not the date. I typed in a complicated prompt — the kind of question I’d have once paid a consultant good money to research for a week. The response arrived in about twenty seconds. Exactly what I needed. In spades.
Eureka. That was the only word for it. I remember thinking, clearly, this changes everything.
And it has. It is the reason this platform exists at all. It gave me — a single proprietor with no team, no budget, no department of specialists — something that could think alongside me, sort through complexity, hold a plan in its head better than I could hold it in mine. It leveled a playing field that had never once, in forty years of working life, been level. That’s not a small gift for a man in his late seventies. That’s the difference between an idea staying an idea and an idea becoming The Encore Project.
I think about my father sometimes when I’m working with it. I wonder what would have happened if someone had handed him a tool that powerful, that conversational, that patient — something that would have let him ask his questions in his own words instead of needing every step written down in order. I’ll never know. He didn’t get the chance. The tools he was offered were rigid, unforgiving of error, built by people who’d never had to consider what it feels like to be a war hero afraid of a keyboard.
The tools available to you now are nothing like the ones that defeated my father. They talk back. They explain themselves. They don’t require you to hold the whole map in your head before you take the first step.
If you’re a man reading this who feels the way my father felt — frozen, certain you’ll embarrass yourself, certain you’ll forget the one step that matters — I want to tell you something simple. The fear is real, and it deserves respect, not dismissal. But the tools available to you now are nothing like the ones that defeated my father. They talk back. They explain themselves. They don’t require you to hold the whole map in your head before you take the first step.
You flew the mission. Whatever your version of that was — whatever room you walked into, whatever decision you made under pressure, whatever thing you did that took real courage — you already proved you have what it takes. This is a smaller kind of brave. I promise you that.
Go find twenty seconds of your own eureka. It’s still out there, waiting.
