Introduction:
“I Should Have Been a Cowboy” – The Dream That Never Rode Off
Some dreams don’t fade because we fail—they fade because life quietly led us elsewhere. Somewhere out West, beneath a sky brushed with dust and memory, a man sits at his window, staring beyond the horizon. He’s not waiting for anything. He’s remembering.
There was a girl once. Her name was Darla. And once, he almost asked her to run away with him. To leave town. To start over somewhere wild and free. She said yes without hesitation—“Just say the word,” she told him. But he never said it. Instead, he tipped his hat, stole a kiss, and rode away like a man who knew his heart wasn’t ready to stay.
Now, years later, he wonders what might have been. What if he had chosen a different path? What if he’d become a cowboy?
He imagines himself with a rope in hand and a six-shooter at his side, galloping across the plains, chasing cattle and dreams. He would’ve had a sidekick with a name only outlaws or old Westerns could love. Together, they’d ride through red rock canyons, track legends like Jesse James, and stare down danger with nothing but grit and laughter.
He thinks of the old cowboy films—Gene Autry, Roy Rogers—the way they sang by the fire, the way they won hearts without even trying. That could’ve been him. That should have been him.
“If I’d been born with spurs and a wider sky,” he whispers, “maybe I’d still be out there.”
The dream never really died. It just sat quietly, waiting behind the years. And now, with time catching up to him, he smiles—not out of regret, but out of quiet defiance.
He looks out the window at the wind rolling across the open land. And with a soft, weathered voice, he says:
“Don’t let the old man in.”
Because sometimes, holding on to a dream is the most cowboy thing you can do.