Chapter 5: The CEO’s Secret Past (That No One Asked For)

Lena flipped through the latest expense reports while her assistant, Oliver, stood across from her, looking ready to faint.

“Lena… just to confirm,” Oliver said, pinching the bridge of his nose. “You want to fund a sports yard for employees using your own salary—which, mind you, is fixed—because you already spent the company’s budget on massage chairs and premium coffee discounts?”

Lena, looking completely unbothered, nodded. “Yes.”

Oliver took a deep breath. “You know, normal CEOs don’t go broke funding their company’s employee benefits.”

She frowned. “But it’s a good idea. Happy employees, better productivity.”

“Yes, but that’s what corporate budgets are for! You don’t have to personally—” He stopped, exhaling sharply. “Never mind. I’ll deal with it. Anything else you want to tell me before I go fight the finance department for your dignity?”

Lena hesitated. “Well… my grandfather suggested I sell my watch.”

Oliver’s eyes lit up with hope. “That’s a great idea! It must be worth—”

“I refused.”

“Of course you did,” he said flatly.

Lena casually adjusted the watch on her wrist. “It’s the only thing I bought with my own money.”

Oliver, already mentally checking out, sighed. “Right. Of course.”

As he turned to leave, he muttered, “I swear, sometimes I feel like you ran an underground business before this.”

There was a pause.

Lena cleared her throat. “About that…”

Oliver stopped mid-step. “Wait. What?”

Lena shifted in her seat. “I mean, not an underground business exactly. It was… a casino.”

A long silence stretched between them.

Oliver’s left eye twitched. “A what?”

Lena looked away, mumbling, “A… small underground casino.”

Oliver stared at her, his soul leaving his body. “A small underground casino?”

She nodded. “It was fun.”

His voice cracked. “Fun?”

Lena folded her arms. “It was just for a while. Nothing illegal. Just… unregulated.”

“THAT’S LITERALLY WHAT ILLEGAL MEANS.”

She waved dismissively. “Not exactly. It was more of an exclusive club. You had to be invited.”

Oliver looked like he needed to sit down. “I—You—WHY?”

Lena shrugged. “I was bored.”

Oliver let out a strangled sound. “You—Aren’t you a rich kid? Why in the world would you run an underground casino?”

Lena looked genuinely confused. “Rich kids aren’t allowed to do business?”

“That’s not—” Oliver closed his eyes and exhaled through his nose. “You know what? No. I am not dealing with this today.”

Lena leaned back. “So you won’t tell Grandpa?”

“Oh, I am telling your grandfather,” Oliver said, already walking away.

Lena blinked. “That’s betrayal.”

Oliver threw his hands in the air. “YOU RAN A CASINO, LENA.”

She sighed and pulled out her phone. “Guess I better book an extra massage chair for stress relief.”

Oliver didn’t even bother responding.

--

The office hum fades into silence, the glow of her monitor dimming like a dying star. Through the glass, the first light of dawn spills in, soft and hesitant, painting the room in hues of gold and gray.

The city below stirs, unaware of her solitude,

as shadows stretch and retreat, fleeting as memories.

She traces the edge of her coffee cup, cold now,

its bitterness a mirror to her thoughts.

The window reflects her face—tired, resolute—

a mask she wears too well, even for herself.

Somewhere, the world is waking, but here, in this quiet space between night and day,

she lets herself remember:

the dreams she once held,

the promises she made,

and the cost of building a legacy

brick by lonely brick.

Lena flicked the poker chip between her fingers, watching the dim office lights reflect off its smooth surface. It was a habit she hadn’t quite shaken, a lingering piece of her past.

Oliver’s reaction earlier had been funny, but if he knew the real reason she started the casino, he probably would’ve had a full breakdown.

It wasn’t just boredom.

She had always been exceptional—a prodigy, a natural at almost everything. People called it talent, genius. But to her, it felt like a curse.

From the moment she could solve puzzles faster than the adults, expectations piled up. Excellence wasn’t celebrated; it was demanded. Achievements weren’t praised; they were expected. And any sign of struggle? Met with impatience, not understanding.

She was given everything but never asked what she wanted.

So when she decided to flip her allowance into something real, it wasn’t just a business move. It was rebellion. It was proof that she could create something on her own terms, without anyone’s permission.

Running the underground casino had been more than making money—it was a lesson in power, human nature, and independence. And yet, even now, after walking away from that world, she still found herself seeking the same thing.

She wanted to build something meaningful. Something that wasn’t just hers by inheritance, but by choice.

Her gaze drifted over the company reports on her desk. Employee benefits, ridiculous gifts, a sports yard—all things that made Oliver want to pull his hair out.

But this was hers.

Lena exhaled and tossed the poker chip into her drawer.

Let them call her impulsive. Let them say she didn’t fit the mold of a proper heir.

She was done playing the role they wanted.

Playing with Fire

Lena had never been afraid of risks. But she wasn’t reckless—she was calculated.

Running an underground casino meant knowing how to keep the game running smoothly, and that required money. Not hers—other people’s.

So she made deals.

The loan sharks saw easy prey in gamblers desperate to chase their losses. She saw an opportunity. She structured agreements, controlled interest rates, ensured that the money flowed but never drowned her operation. The loan sharks respected her because she was smart enough to guarantee their profit while keeping her customers playing.

But then came the gangsters.

They were different from the businessmen in suits she had grown up around. More direct. More dangerous. Less talk, more action.

“You’re a rich girl playing a dangerous game,” one of them had said, a gold chain peeking out from his collar as he leaned back, watching her with amusement.

Lena had only smiled. “And you’re in my casino, taking my drinks, waiting for my money to move. So tell me, who’s really in charge here?”

They had laughed. They liked her.

Not in a friendly way—but in a way that meant they respected her enough to not cross her. She played the game better than they expected.

She always had an exit strategy. Always had leverage.

Until one night, when she looked around and realized she was done.

She didn’t fear them—she had outmaneuvered worse. But she had seen enough. She had watched too many people lose themselves, too many desperate eyes searching for salvation in a game that only took.

So she walked away.

Now, years later, sitting in her high-rise office, fighting for coffee discounts and sports yards, she sometimes wondered if she had truly left that world behind.

But no one here knew who she had been.

And maybe that was for the best.

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