The rule of my life is to make business a pleasure, and pleasure

Host: The evening sun spilled through the tall windows of the old lounge, casting ribbons of gold across the marble floor. The air was thick with the scent of aged whiskey, leather, and faint traces of cigar smoke. Outside, the city shimmered in the twilight — towers gleaming like blades, the hum of ambition still echoing from the day.

Jack sat at the bar, his jacket draped over the stool beside him, tie loosened, sleeves rolled up to his elbows. He stirred his drink lazily, watching the ice collapse into itself. Jeeny entered from the far side of the room — composed, radiant, with that quiet kind of elegance that comes from knowing exactly where she stands. She carried a folder under her arm, her posture a balance of grace and will.

She sat beside him, ordered sparkling water, and turned slightly toward him.

Jeeny: “Aaron Burr once said, ‘The rule of my life is to make business a pleasure, and pleasure my business.’”

Host: The words hung in the air, heavy and smooth as bourbon. Jack glanced sideways, a smirk tugging at the corner of his mouth.

Jack: “That sounds like something a charming villain would say before stealing your fortune.”

Jeeny: (smiling) “Or your heart.”

Jack: “Or both.”

Host: He took a slow sip, eyes narrowing with amusement. The room’s low jazz melted into the background, the bass line pulsing like a heartbeat.

Jack: “You really admire Burr? The man shot Hamilton over pride and politics.”

Jeeny: “I’m not defending his duels. I’m talking about his philosophy. The man understood balance — how to merge ambition and joy. How many people can say that about their work?”

Jack: “Balance?” (chuckles) “He called it business; I call it opportunism. Burr didn’t blur pleasure and work — he weaponized them.”

Jeeny: “Maybe. But that’s because he refused to separate them. He lived like the two were one — that’s why he mattered.”

Jack: “Until he didn’t. History turned him into a footnote with a scandal. A man who wanted to enjoy the game too much to win it cleanly.”

Jeeny: “And yet here we are, still talking about him.”

Host: Her eyes caught the dim glow of the bar light — sharp, alive, unafraid. Jack met her gaze, leaning closer.

Jack: “So, what are you saying? You want to live like Burr? Make business your pleasure — turn the grind into flirtation?”

Jeeny: “I want to find joy in ambition. You work yourself into exhaustion, Jack. You talk about success like it’s a battle scar.”

Jack: “Because it is. Every contract, every deal — a fight to stay relevant. You think this city rewards people who slow down to ‘enjoy’ it?”

Jeeny: “Then maybe you’re not building a career. Maybe you’re just surviving one.”

Host: The bartender poured another drink nearby, the sound of liquid over ice filling the silence between them. Jack looked down at his glass, a faint smirk fading into something quieter — almost reflective.

Jack: “You know what pleasure does, Jeeny? It makes people weak. It distracts. You take your eye off the deal, someone else closes it.”

Jeeny: “You mistake exhaustion for strength. Pleasure isn’t distraction — it’s fuel. People like Burr, like Da Vinci, like Coco Chanel — they didn’t separate work from joy. They made creation their indulgence.”

Jack: “Da Vinci wasn’t negotiating with clients who wanted cheaper art.”

Jeeny: (leans in) “But he was negotiating with kings. The stakes haven’t changed, Jack — just the currency.”

Host: Her words struck something in him — not anger, but recognition. He turned away from her gaze, eyes catching the reflection of the city lights in the bar mirror.

Jack: “You really believe business can be pleasure?”

Jeeny: “It has to be. Otherwise, it’s just survival dressed in a suit.”

Jack: “That’s idealism. People chase success because they want freedom, not joy.”

Jeeny: “Then why do most successful people look miserable?”

Host: The question landed hard. Jack didn’t answer. He watched a man at the far end of the bar laugh loudly — a face he recognized, a competitor, one of those executives who wore his smile like armor. Jack wondered, briefly, if the man was happy or just good at acting like it.

Jeeny: “When was the last time you worked on something you loved — not because it paid well, but because it made you feel alive?”

Jack: (after a pause) “College. I designed a community theater project. It failed.”

Jeeny: “But you remember it.”

Jack: “Yeah. I remember it.”

Jeeny: “Then maybe that was your pleasure, before business killed it.”

Host: Her voice softened on that last word — killed — as though it wasn’t an accusation but an elegy. The light flickered overhead. Jack ran his hand through his hair, a small sigh escaping him.

Jack: “You think pleasure can save me from burnout?”

Jeeny: “No. I think remembering what pleasure feels like can.”

Host: The bartender refilled his glass. Jack didn’t stop him this time. He looked at Jeeny, a smile tugging back at the edge of his face, this time less defensive — more curious.

Jack: “You’re quoting Burr like a prophet. But he also ended up exiled, broke, and hated.”

Jeeny: “And still unforgettable.”

Jack: “That’s not success.”

Jeeny: “No. That’s immortality.”

Host: She leaned back, crossing her legs, her silhouette framed by the warm glow of the city outside. Jack tilted his glass, the whiskey catching firelight as if considering her words through its amber depths.

Jack: “So you’d risk everything — comfort, stability — for the pleasure of creation?”

Jeeny: “Of course. What’s the point of wealth if it buys you a life you can’t enjoy living?”

Jack: “Pleasure fades.”

Jeeny: “So does profit. But meaning — that lingers.”

Host: The music changed — a slow, soulful saxophone filling the room with longing. The last patrons began to drift out, leaving only the two of them and the bartender polishing glasses in quiet rhythm.

Jeeny reached for her glass, took a small sip of her water, and smiled faintly.

Jeeny: “You know, Jack, maybe Burr’s rule wasn’t about greed or indulgence. Maybe it was about integration — living without compartments. The same hands that sign contracts should also know how to hold a moment.”

Jack: (quietly) “That’s poetic.”

Jeeny: “So was he, before the world made him infamous.”

Host: He laughed then — low and genuine. Something in him loosened, a rare, fleeting ease. He set down his drink and looked at her, his eyes softened by the kind of understanding that feels earned.

Jack: “Maybe I’ll try it. Make business a pleasure again.”

Jeeny: “And pleasure your business?”

Jack: “Why not? Seems like the only rule worth breaking.”

Host: The rain had started outside — gentle, persistent — tapping against the glass as the city dimmed. Jeeny stood, gathering her things, then paused at the doorway and looked back.

Jeeny: “Don’t forget, Jack. Burr lived dangerously, but he lived fully. Maybe that’s the only success that matters.”

Host: Jack raised his glass slightly — a toast to something unseen — and watched her step into the rain. The door closed softly behind her, leaving him with the echo of her words and the reflection of his own face in the bar mirror.

For the first time in years, it looked like a man not surviving, but living.

Host: The lights dimmed, the music swelled, and as the night deepened, Jack smiled — the faint, unguarded smile of a man rediscovering what it meant to find pleasure in the work of being alive.