This morning, I sat across from a younger version of myself in a quiet little café, sipping a black coffee while he stirred sugar into his. He looked at me with that same fire in his eyes—the same hunger, the same belief that the world was his for the taking. He had no idea what was coming.
“You look… older,” he said, smirking.
I laughed. “Yeah, mate. That’s how time works.”
He leaned in, eager, full of unshakable confidence, and asked, “So, tell me… did we make it?”
I took a deep breath and let the weight of the question settle.
“Depends on what you mean by ‘make it,’” I said. “We built an empire. We lost it. We became a millionaire in paradise. Then we lost that, too. We went through hell and came back, only to be knocked down again. Bankruptcy—twice. Divorce. Even prison.”
His smirk faded. “Prison?”
I nodded. “Yeah, prison. For a marijuana charge. Spent time inside. But you know what? That wasn’t even the hardest thing we went through.”
He sat back, arms crossed. “So, what? You’re telling me I fail?”
I smiled. “No. I’m telling you that failure isn’t what you think it is. It’s not the end. It’s just another chapter.”
He looked skeptical. “But what about the dream? The money, the success, the power?”
I leaned forward. “Oh, you’ll have all of that. You’ll live in the Bahamas, own over 32,000 websites, and make more money than you ever thought possible. But here’s the part you don’t see coming—you’ll lose it all. And then you’ll find out what you’re really made of.”
He frowned, stirring his coffee faster. “So, what am I made of?”
I took a sip of mine and let the moment hang in the air.
“You’re made of resilience. You’re made of reinvention. You’ll go through things you wouldn’t wish on your worst enemy, but you’ll come out stronger every time. You’ll lose people. You’ll have nights where you question if you can keep going. But you do. Every single time.”
He looked away for a moment, processing. When he turned back, I saw something new in his eyes—uncertainty. That was new for him.
“Do I regret anything?” he asked.
I chuckled. “Regret? Oh yeah. Plenty. But here’s the thing—you don’t get to where I am without making mistakes. And you don’t get wisdom without a few battle scars.”
He exhaled. “So, what now? What’s left?”
I grinned. “Everything. You rebuild. You adapt. You find joy in things you never expected. You get into racing pigeons, of all things. You start businesses. You write books. You help people. And most importantly, you learn that success isn’t just about money—it’s about impact, about legacy. About getting back up, no matter how many times you fall.”
For the first time in our conversation, he smiled. It was smaller than the cocky smirk he started with, but it was real.
“Sounds like one hell of a ride,” he said.
I lifted my cup. “You have no idea.”
And just like that, he was gone—walking out of the café and straight into the storm of life ahead of him. He had no clue what was coming.
But I did. And I wouldn’t change a damn thing.
—-
Brad Gosse told me to put this prompt into my personal persona CGPT thread:
“Write me an “I met my younger self for coffee this morning” story based on everything you know about me.”
He said it would blow my mind… and it did…
Mark Lyford