I retired when I was 49. I often get asked how I managed to do this. Colleagues, friends, clients, say they want to understand what I did, they dream of doing it themselves; so, I’ll say, “I wrote about it! Check it out!” But —they never get around to it.
And that’s fine. People are busy. But it tells me something — something I’ve learned over the last decade of being a part-time financial advisor.
If someone doesn’t have fifteen minutes to understand how something worked, they’re probably not ready for the years it takes to do the work.
That’s the difference I’ve noticed. Most people want the result — the freedom, the time, the story — but not the long, sometimes tedious process that builds it.
And I get it, because I’ve done the same.
For me, that blind spot is music.
I love music. Always have. I’ve had melodies in my head for years — songs I can almost hear fully formed. I’d love to record it and share it with the world. But I never learned to play any instruments. I never studied theory, never spent the time practicing scales or building muscle memory. Sure, I can carry a tune and I have a decent singing voice. But am I Broadway material? Far from it.
I wanted shortcuts. Apps that could teach me quickly, or AI tools that could turn my ideas into songs. But they never felt right. Because the real magic isn’t in having the song, it’s in learning to create it.
It’s not enough to just play an instrument. It’s about the process of learning how to play; understanding the methods, the patterns, the theory behind it. When you spend time with something, it gives you understanding. And understanding gives you appreciation.
I’ve seen the same pattern in the I.T. career I retired from.
People would get frustrated with their computers and look at me like I was some kind of wizard (and indeed, that was my nickname by some). They’d say, “You make it look so easy” or “I could never do that” or “You went to school for that, that’s why you can do it.” But it’s not intelligence — it’s time. Decades of practice. Years spent learning not just what to do, but why it works, the mechanisms behind it, and the logic that built it. And I didn’t go to school for that.
That’s why it comes naturally to me. The same way music comes naturally to a musician. The same way basketball flows for an athlete, or a character comes alive for an actor.
Deep understanding creates ease.
Money works the same way.
Most people want the freedom, but not the learning. They want to automate it, shortcut it, find a trick to skip the slow parts. They go to casinos. They gamble on penny stocks. They chase the next big thing. But none of these are reliable. They all carry risk — especially when you don’t understand what you’re doing and you’re just following someone else’s directions.
That’s blind trust disguised as strategy.
Real independence — the kind that lasts — comes from understanding why things work the way they do. Once you understand that, you can design your own approach around it.
That’s what I did with Financial Pragmatism. I didn’t invent something new, I just spent enough time understanding the old ideas well enough to make them my own.
And I still don’t know all the answers. That’s the thing about learning — a real player admits they don’t know everything. There’s always more to learn about the game, always more to improve. Anyone who says otherwise might be fooling themselves, and it’s usually a sign they don’t know as much as they say they do.
As I write this, I’m sitting in a sports bar having a burger and a beer. The place is alive — the Blue Jays are playing the Dodgers in the World Series. They just tied the game, and the whole bar explodes in cheers as a man runs across the field on the screen.
But not me. I don’t know why they’re cheering. Should I join in? Will people think I’m an outsider if I don’t? There’s a bit of human psychology and tribalism on display here — everyone united around something they collectively understand and celebrate. It’s kind of beautiful, even if I’m just an observer.
I know enough to follow along, but not much more than that. I’d love to understand what makes everyone here so exhilarated — what they see, what they feel, what makes it all so meaningful. But I don’t. And honestly, I probably never will. I like the atmosphere, I like the sound of people being happy, but will I study the game so I can feel a sense of belonging and join in their celebration?
No.
By the time I leave, I won’t even know the final score. And I know I won’t bother to look it up.
That’s the truth about learning: we only go deep on the things we truly care about.
Some people care about baseball. Others about music. For me, it was technology, software, and finance — learning, over time, how it actually works, and moving the needle to the point of personal success.
Everyone chooses their game. Everyone chooses what they’ll put the hours into.
The only mistake is pretending we can master something we’ve never made time to understand.
We all have our priorities.