Humans logo

I Worked in a Prison for Years. Here's What I Learned About Why Men Fail.

A former jail warden shares what years behind bars taught him about why men keep failing on the outside.

By George De JaarPublished 5 months ago • 3 min read
I Worked in a Prison for Years. Here's What I Learned About Why Men Fail.
Photo by Lawrence Crayton on Unsplash

I didn't learn this in a classroom. I learned it watching men through bars.

For years I worked as a jail warden. Before that I served in the military. After that I spent years on a mine and eventually helped build a solar farm. I've worked in environments most people only see in movies — and in every single one of them, I watched the same pattern destroy men.

Not laziness. Not bad luck. Not lack of talent.

The inability to stick to one thing.

What I Saw Inside

When you work in a prison, you have a lot of time to observe people. You see men at their lowest. And if you pay attention — really pay attention — you start to notice something that nobody talks about.

Most of the men I watched weren't stupid. Many of them were sharp, funny, capable. They could have built something real on the outside.

But they never did. And when you talked to them honestly, the pattern was always the same. They chased angles. They jumped from one plan to the next. They were always looking for the fast way — the shortcut — instead of building slowly on one solid foundation.

Every time one thing got hard, they moved to the next thing. And the next. And the next.

Until one day there was nothing left to move to.

This Isn't Just a Prison Problem

I want to be clear — this pattern doesn't only live behind prison walls. I saw it in the military too. Smart soldiers who drifted after service because they couldn't find one direction to commit to. I saw it on the mines — talented men who burned through three different trades because none of them were exciting enough for long enough.

And when I spent three years out of formal work, managing a household and figuring out my next move — I saw it in myself.

I kept looking at opportunities. New ideas. Better paths. Anything that felt like progress without requiring me to sit in the discomfort of building something slowly.

That's the trap. And it catches almost every man at some point.

The One Thing That Separates the Men Who Make It

In every environment I worked in, there were always a few men who quietly built something solid. They weren't the loudest. They weren't the most talented. But they shared one quality that set them apart from everyone else.

They picked one direction and they didn't move from it — no matter how boring it got, no matter how slow the progress was, no matter what else showed up and looked shinier.

That's it. That's the whole secret.

Not a special skill. Not luck. Just the decision to stay the course when everything around them was screaming to quit.

What I Wish Someone Had Told Me

Nobody sat me down when I was young and explained that the exciting feeling you get when you start something new — that rush of possibility — is just your brain doing what it was built to do ten thousand years ago.

Nobody told me that feeling always fades. That it's not a sign the opportunity is wrong. It's just what happens when the novelty wears off.

Nobody told me that the men who win aren't the ones who never want to quit. They're the ones who know what to do when the urge hits.

I had to learn all of that the hard way. Across different careers, different countries, different environments. Through failure and frustration and a lot of wasted years.

And eventually I wrote it all down — everything I learned about why men get stuck in the shortcut trap and exactly how to break out of it.

If This Resonates With You

I put everything into a short, honest guide called The Long Game — A No-BS Guide to Stopping the Shortcut Trap.

No theory. No fluff. Just real talk from a man who has worked in some of the toughest environments in the world and watched what separates the men who build something from the men who don't.

Get it here: https://dejaar.gumroad.com/l/thelonggame

If you're a man who keeps starting over and wonders why nothing ever sticks — this was written for you.

George de Jaar is a South African writer and former soldier, jail warden, and mine worker. He writes about discipline, real life, and playing the long game.

advice

About the Creator

George De Jaar

Soldier. Jail warden. Miner. Construction worker. Writing about real life, discipline and playing the long game. 🇿🇦

Enjoyed the story? Support the Creator.

Subscribe for free to receive all their stories in your feed.

Subscribe For Free

Reader insights

Comments

There are no comments for this story

Be the first to respond and start the conversation.

Sign in to comment
    Written by George De Jaar