Elevator of Regrets

Singapore was where men went to forget. I had a storage unit full of inventory, a distribution deal with ZMC, and a life that revolved around hotel rooms, conference calls, and meetings over overpriced whiskey. My main office? Marriott, room 2862. I was a permanent resident of the 28th floor, where the elevator was always packed with silent men in suits, their gazes fixed on some invisible point beyond the doors. No one spoke. Not from level one to level two, not from level three to level five. Just dead silence.

Unless, of course, it was one of the other guests—the bloated businessmen with gold bands cutting into their sausage fingers, accompanied by girls barely old enough to order a drink in the U.S. Mini-skirts, vacant stares, clinging to these men like stray cats looking for a warm place to sleep.

“Can you hit floor 30 for me?” one of them would ask.

“Sure, buddy,” I’d say, pressing the button.

Elevator of regrets.

That’s what I called it.

The ride up was like watching a slow-motion train wreck of moral collapse. And I was no different. My friends and I—if you could even call us that—were all drowning in some form of excess. Alcohol, food, status, prostitutes. Everyone had a vice. Everyone had a reason to be there. I wasn’t buying women, but I was buying everything else. Expensive suits, lavish meals, nights that ended in fogged-up glass and the taste of liquor thick in my throat.

I had breached 330 pounds without even realizing it. My clothes barely fit. My breath came in short, heaving gasps when I walked more than a few blocks. My reflection in the mirror was a swollen version of a man I barely recognized—dark, hollowed eyes, bloated face, skin stretched over indulgence and exhaustion.

And still, I stayed.

Because home wasn’t home.

Home was a transaction.

Money wired, bills paid, no calls of Dad, we miss you, no late-night texts from a wife who still wanted me, no reminders that I was anything more than a paycheck. I could have died in Singapore, and they would’ve just checked their bank account. If the balance was still good, then I was still alive. That was the only metric of my existence.

My kids’ mother had raised them well. They had learned from her example—take, take, take. A bottomless hunger with no gratitude. They’d ask for things with the entitled tone of people who had never had to earn a damn thing in their lives.

Father’s Day? Nothing.

Birthdays? Silence.

But Mother’s Day? Oh, Mother’s Day was an event. Cards, gifts, an all-day celebration for the woman who had poisoned them against me.

And every time, I’d sit there in some high-rise bar, staring at my phone, wondering why the fuck I was still playing this game.

Lucid Moments in Thailand

It was just another trip. Just another deal. Another handshake, another dinner, another round of drinks at some Bangkok rooftop lounge where men measured their worth in the size of their liquor tabs. We had just secured Lucent Technology as a client, and now we were after Amphibian. Another late night, another battle against jet lag and the slow rot of self-destruction.

Then my phone rang.

Steve Ho. ZMC’s top guy. My drinking buddy, my karaoke partner, the guy who once got blackout drunk and somehow ended up naked in a sauna full of Russian businessmen. He wanted to meet.

“Now?” I asked, already exhausted.

“Now.”

Fine.

I threw on something presentable, rode the elevator down past the regret-filled corridors, and met him outside. We sat at one of those little food carts, cheap plastic chairs sinking into the sidewalk, the air thick with humidity and the scent of grilled meat.

I expected business talk. Instead, he stared at me, studying me in a way that made me uncomfortable.

“You look like shit,” he finally said.

I laughed. “Thanks.”

“I’m serious.” His face didn’t change. “You’re dying in front of me, and you don’t even see it.”

The words hit harder than I expected.

“You drink too much. You eat too much. You never sleep. You don’t talk about your family, you don’t seem excited to go home. Your phone never rings. Your wife never calls. Your kids never check on you.”

I opened my mouth to respond, but he kept going.

“I’ve seen people like you before. They burn out. They either change, or they die young.” He leaned forward. “You have more than enough money. You’re successful. But you are not happy.”

I sat there, staring at the table, my drink untouched.

He was right.

I hadn’t been happy in years.

I wasn’t even unhappy. I was just existing.

Going through the motions.

A machine programmed to earn, to function, to sustain.

Something inside me cracked that night. Not a big break. Just a tiny one, like the first hairline fracture in a windshield. But I felt it.

I barely slept. Spent the whole night pacing, staring out over Orchard Road from my hotel window, watching the city pulse with life while I felt like a ghost.

The Exit Plan

The next morning, I ran the numbers.

I had some software from Thailand—something that let me break everything down, analyze my financials like a problem to be solved. I worked backward, calculating exactly how much I needed to never work again.

I landed on commercial real estate.

Stocks were bullshit. Mutual funds were just an excuse to let someone else take a cut of your money. But property? Property was tangible. It was something I could control. Something I could hold. Something that wouldn’t evaporate because some billionaire decided to start a war.

I made my decision.

Two weeks later, I flew home. Two weeks later than I was supposed to.

Nobody noticed.

The Whisker Basket

Back in the States, I found the first property—some small commercial space on Galveston Road in Bend, Oregon. A hairdresser was renting it out. The numbers looked good. I called the real estate agent.

Enter Scott Wicklund.

He thought he was going to have to sell me on the place. He had no idea I had already made up my mind.

I wired $310,000 in cash.

And that was it.

My first investment. My first step out of the life that had been eating me alive.

Scott got his commission. I got a whisker basket full of fruit.

That was his thank you—a goddamn basket of oranges and apples wrapped in plastic.

I stared at it, then at him.

“That’s it?”

He laughed. “What else do you want?”

I smirked.

“I want you to fly to Utah with me and buy another property.”

He hesitated. Said he’d think about it. Said he had church on Sundays and Bible study on Wednesdays. Said his wife probably wouldn’t like it.

I wasn’t interested in excuses.

“You want my business? You fly to Utah with me. No more baskets.”

Scott Wicklund had never met someone like me before.

By the end of it, he wished he never had.

 

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James O

Born behind a Tommy’s Burgers to a mother I had to divorce at thirteen, just to survive. I was homeless in Los Angeles by sixteen, armed with nothing but a backpack full of rage. I clawed my way out through a crooked high school diploma and a failed stint in the Navy that got me ninety days in the brig and a boot back to the street.

I decided the world wasn't going to give me a damn thing, so I took it. I went from the shipyards to drafting rooms to building my own engineering firms. I learned the game, held my ground against the suits, and became a self-made millionaire with an office in Singapore before I was thirty. I chased the American Dream and, for a while, I caught that bastard by the throat.

Then I did the stupidest thing a man can do: I retired at thirty-five. Thought I could buy peace. I built a fortress of money and success on a yuppie ranch in Oregon, a monument to everything I’d survived. But the cage wasn't to keep the world out; it was to keep me in. And the one person I handed the key to, the one I trusted inside my walls? She turned out to be a ghost, wearing the face of the same damn madness I’d spent my whole life trying to outrun.