I can honestly say I don’t have very many regrets, mostly because I don’t look back long enough to let them settle in. I usually just keep moving, forward, sideways, diagonally—doesn’t matter. Whatever direction the wind’s blowing, I ride it until I’m either burned out or bored. That’s how it’s always been. But every now and then, something gets under my skin, sticks to me like old chewing gum on the sole of my shoe, and no matter how much I scrape at it, it’s just there.
This is one of those stories.
I had this friend, James—same name as me, but we were cut from different cloths. He was smart, well-spoken, never married, no kids, no real obligations except to himself. He was the kind of guy who could blend into a crowd but also had this quiet presence that made people listen when he spoke. He was solid, dependable, and, most importantly, not an asshole. He wasn’t one of those guys who turned into a sweaty, desperate creep the second a woman walked into a room. You know the type—leaning in too close, trying too hard, throwing money at women like it was some kind of carnival game. No, James wasn’t like that. He was content in his own skin, which was rare.
One day, he takes off to Thailand. Three months of whatever the hell he was doing over there—probably sitting on a beach, drinking cheap beer, watching the world move slower than it ever could in the U.S. He comes back, glowing, swearing up and down that he’s figured it all out. Says he’s leaving again, this time for six months. He’s in his late 40s, maybe pushing 50, and he’s got nothing holding him back. Then his father dies, and suddenly, he’s got $400,000 in cash—not millions, but enough to tell the world to go fuck itself for a long time if he plays his cards right.
He’s all in. This is it. He’s never coming back.
Before he leaves, he asks if he can park his Volvo and his mountain bike at my place. Sure, why not? It’s not like I had a plan for them. But while he was gone, I pulled the trigger on my divorce. My kids’ mother and I were finally, officially, done.
James comes back, grabs his car, sells his bike, and that was it. Gone for good. Every so often, he’d send messages from paradise—pictures of his life, his women, his ocean. He’d tell me about the cost of living, how easy it was, how much better it all was when you just fucking leave.
And he tried to sell me on it. Said I could do the same thing. Not with the Thai girls, since I never had a thing for Asians—hence why I never cheated on my wife in Singapore—but maybe with the Russians. He had this connection, some woman named Yana.
At the time, my life was on fire. I was drinking too much, running a restaurant, surrounded by leeches, bleeding money left and right on people who only liked me when the drinks were flowing and the tabs were open. And for the first time, I listened. I let myself entertain the idea of an exit strategy, an escape hatch. I started talking to Tonya.
She was direct. Russians don’t do small talk. There was no “Let’s see where this goes”—no, it was “Why are you waiting? Just come.”
And she had a point.
She told me, “James, you’re already broke. You’re already exhausted. You’re already drinking yourself stupid. What are you holding on to? It costs one plane ticket. One. That’s it. You’ll figure out the rest.”
And I believed her.
I let myself believe that maybe, just maybe, I could walk away from everything.
But I didn’t do it.
I told myself it was because of my kids. But they didn’t even want to spend time with me.
I told myself it was because of my friends. But those bastards were just using me for free food and drinks.
I told myself it was because I needed more money. But how much more? Enough to waste another five years? Another ten?
I said no.
And that’s the regret.
Not because I wish I had done it. Not because I think I’d be happier if I had. But because it was the first time in my life that I let fear make my decision for me.
I was afraid.
Not of moving, not of change. But of the unknown.
The little voice inside me—the one that had always pushed me forward, told me when to make my move, when to take the gamble, when to trust my gut—that voice was screaming at me. And I ignored it.
That’s what I regret. Not the lost opportunity. The lost faith in myself.
It took moving to Sedona to get my head straight. To figure out what the hell I actually wanted, what kind of man I wanted to be.
And here’s what I realized:
Some people are meant to build. Others are meant to burn.
Some men build houses, grow old inside them, sit in the same chair every night until their bodies give up and their wives call the funeral home. That’s one kind of life.
And some men burn through everything—jobs, cities, lovers, expectations—because they can’t stand the idea of being stuck.
James was a burner.
So was I.
But here’s the thing—you can’t let the fire go out, and you can’t let it consume you.
That’s the balance. That’s the real trick.
I could have gone to Thailand. I could have woken up next to a Russian on a beach. Maybe I’d have been happy. Maybe not. But I didn’t go. And now?
Now, I make damn sure that the next time that little voice tells me to move, I listen.
Because fear?
Fear is the only thing that actually kills a man.
