You must avoid giving hostages to fortune, like getting an

Host: The evening had settled softly over the city, wrapping its streets in the kind of quiet that only follows long, tiring days. Through the windows of a dimly lit apartment, the last traces of sunlight filtered in—thin, amber lines falling across a desk cluttered with papers, half-drunk coffee, and a typewriter that hadn’t spoken in weeks.

Jack sat there, hunched, a cigarette between his fingers, its smoke curling upward like a question never answered. His grey eyes were sharp but hollow, reflecting the tired glow of the desk lamp.

Across the room, Jeeny stood barefoot by the window, her silhouette outlined by the flicker of neon signs from the street below. She was dressed simply—no jewelry, no makeup—just presence. The kind that carried calm and fire in equal measure.

The clock on the wall ticked slowly, like a heartbeat running out of patience.

Jeeny: “Irwin Shaw said once—‘You must avoid giving hostages to fortune. Like getting an expensive wife, an expensive house, and a life that keeps you too busy to write what you wish.’”

Jack: “Yeah.” (He exhales a plume of smoke.) “I know the line. It’s what every failed writer tells himself before blaming the mortgage.”

Jeeny: “It’s not about blame, Jack. It’s about freedom. About what we trade for comfort.”

Jack: “Freedom’s a luxury, Jeeny. And luxury costs money.”

Host: The lamp buzzed softly, its light trembling over the yellowed papers scattered before him—unfinished drafts, rejected stories, ghosts of sentences he once believed would change something.

Jeeny: “No, Jack. Freedom costs courage. Money just buys silence.”

Jack: “That’s rich coming from someone who doesn’t have bills stacked on the kitchen counter.”

Jeeny: “I have them. I just don’t let them own me.”

Jack: “No one chooses to be owned. It happens slowly. You start with a plan, then life starts collecting payments.”

Host: He stubbed out the cigarette in a chipped ashtray, the motion sharp, irritated—but beneath it, exhaustion.

Jack: “Look, Shaw could talk like that because he was already successful. It’s easy to tell people to ‘avoid hostages’ when you’ve already made your fortune.”

Jeeny: “He said it because he knew what fortune does to people. How it traps you in golden cages, how it teaches you to measure your dreams by invoices and deadlines.”

Jack: “You make it sound like ambition’s a crime.”

Jeeny: “Not ambition. Attachment. The moment your art becomes dependent on comfort, it stops breathing.”

Host: The room fell silent. Outside, a car horn cut through the night, followed by the hum of distant voices—ordinary lives unfolding without the burden of philosophy.

Jack: “So what? We’re supposed to starve for authenticity? Live in a box and call it integrity?”

Jeeny: “Maybe just remember that the box you live in can become your prison if you fill it with too much furniture.”

Jack: “That’s poetic, but not practical.”

Jeeny: “Neither is regret.”

Host: Her words landed like a quiet strike—soft, but deep. Jack looked up from the desk for the first time, really looking at her.

Jack: “You think I’m a coward, don’t you?”

Jeeny: “No. I think you’re afraid of losing what you’ve built. Even if what you’ve built is keeping you from living.”

Jack: “You think it’s that simple?”

Jeeny: “It’s never simple. But it’s clear. The man who ties himself to comfort will never take the risks that make his soul worth knowing.”

Host: The rain began outside—light at first, then steadier. It slid down the windowpane in silver streaks, as if time itself were melting.

Jack: “You know, there was a time I used to write all night. Back before… all this.” (He gestures vaguely at the apartment, the walls, the weight of adult life.) “I thought I’d be someone by now.”

Jeeny: “You are someone. You’re just not the one you wanted to be.”

Jack: “And what if I can’t go back?”

Jeeny: “Then you move forward—but lighter. Stop dragging the furniture of your fears.”

Host: Jack leaned back, his hands resting on his knees, the smoke from his last cigarette still hanging faintly in the air like old guilt.

Jack: “You really think we can live like that? Detach from everything—love, money, comfort—and still have something left to write about?”

Jeeny: “That’s the irony, isn’t it? You think detachment means emptiness. But sometimes, it’s the only way to fill yourself again.”

Jack: “And what about love?”

Jeeny: “Love’s not a hostage unless you make it one. Real love doesn’t ask for your chains. It asks for your truth.”

Jack: “You sound like you’ve never lost anything.”

Jeeny: “I’ve lost everything I ever thought I needed. That’s how I learned what I actually can’t live without.”

Host: The thunder outside rolled low and distant, the kind that feels more like a warning than a sound. Jack stared at the typewriter—the cold, silent beast of his own creation.

Jack: “You ever notice how every great writer dies poor or broken?”

Jeeny: “Or alive, if you measure differently.”

Jack: “Alive doesn’t pay the rent.”

Jeeny: “Maybe not. But death in comfort isn’t much of a bargain either.”

Host: The rain began to ease, leaving behind the faint smell of wet earth and electricity. Jeeny crossed the room and sat across from him, close enough that their reflections merged in the dark window.

Jeeny: “You built your life like armor, Jack. Expensive, heavy, impressive. But you can’t write through steel.”

Jack: “So what—sell the car, leave the job, throw myself into the void for a novel no one might ever read?”

Jeeny: “If it’s the truth, yes.”

Jack: “You’d really do that?”

Jeeny: “I already did.”

Host: Her eyes held his—steady, unwavering. There was no arrogance in her voice, just quiet conviction. Jack looked away first. The typewriter’s black keys seemed to glimmer faintly in the lamplight, waiting.

Jack: “You know, I used to think people like you romanticized struggle. Now I think maybe I’ve just grown comfortable with my own.”

Jeeny: “Comfort’s the most dangerous addiction there is.”

Jack: “And risk is the cure?”

Jeeny: “No. Honesty is.”

Host: The clock ticked louder now. Or maybe it was just the room growing quieter. Jack reached forward and placed his hands on the keys—hesitant, uncertain.

The first sound was small: click. Then another. Then a rhythm began, fragile but alive.

Jeeny smiled faintly, watching him begin again.

Jeeny: “You see, that’s the thing about hostages. They stop being prisoners the moment they decide to walk out.”

Host: The lamp flickered once more, casting the shadow of a man rediscovering movement. The rain outside had stopped. The city glowed again, reflected in the window like a second chance.

Jack kept typing. Each word landed heavy, imperfect—but true.

Jeeny stood, walked to the window, and looked out at the wet streets below, where people hurried under umbrellas, carrying the weight of lives built on fortune and fear.

Host: “You must avoid giving hostages to fortune,” Irwin Shaw had said.

And in that dim room, between the hum of rain and the clicking of keys, a man began to ransom himself back—one sentence at a time.

Host: The lamplight glowed warmer now, as if the universe had leaned in to listen. For the first time in a long while, Jack wasn’t just surviving. He was writing.

And perhaps that was freedom enough.