Any man who has $10,000 left when he dies is a failure.

Host:
The bar was old, the kind that carried the ghosts of better nights. Mahogany counters scarred with history, brass taps dulled from years of stories poured over them. The air smelled of smoke, whiskey, and time — the three ingredients of both ruin and revelation. Outside, the city pulsed in wet neon, the sound of rain and traffic bleeding faintly through the window.

Jack sat at the bar, his glass half-empty, spinning a coin between his fingers. Across from him, Jeeny sat in the corner booth, legs crossed, eyes sharp but tired, her drink untouched. Between them, the air hummed with that quiet tension born not of argument, but of understanding too heavy to carry easily.

Jeeny: “Errol Flynn once said — ‘Any man who has $10,000 left when he dies is a failure.’”
Jack: [grinning faintly] “Now there’s a philosophy I can toast to.”
Jeeny: “You would. He lived like every day was a stunt scene.”
Jack: “And died like it was the last take.”
Jeeny: “Do you think he meant it — really? Or was it just another rebellion dressed as wisdom?”
Jack: “Both. The man lived like money was a rumor and time was an accomplice. Maybe he wasn’t wrong.”
Jeeny: “Or maybe he just mistook recklessness for freedom.”
Jack: “Is there a difference?”
Jeeny: “Only in who’s left to clean up the wreckage.”

Host:
A jazz tune played softly through an old speaker — trumpet, bass, and nostalgia. The light above the bar flickered, catching the rim of Jack’s glass. He raised it slightly, staring at the amber liquid as if it held something sacred.

Jack: “You know, Flynn’s quote sounds outrageous until you realize he was talking about life as currency. Not cash — vitality. Ten thousand left over meant ten thousand unlived.”
Jeeny: “But isn’t that arrogance disguised as philosophy? Not everyone can afford to burn life at both ends.”
Jack: “Maybe. But he wasn’t talking about privilege — he was talking about fear. People save for safety, not for joy. They hoard years like coins.”
Jeeny: “And he spent both recklessly.”
Jack: “Exactly. Because he understood the cruel math of mortality: you can’t take balance sheets to the grave.”
Jeeny: [sipping her drink] “And yet, the grave always takes interest.”

Host:
The bartender wiped down a glass, pretending not to listen but clearly listening. Outside, a taxi hissed through a puddle, throwing light across the window like liquid gold. Jeeny’s reflection flickered, and for a brief second, she looked like someone caught between admiration and warning.

Jeeny: “You ever notice how people who live like that — Flynn, Hemingway, Dean — they all burn out early? Maybe the universe charges extra for passion.”
Jack: “Or maybe the universe rewards authenticity, even if it’s short-lived. Flynn wasn’t pretending. He knew life was a performance that didn’t guarantee an encore.”
Jeeny: “But isn’t there a kind of cowardice in excess? Using pleasure to drown silence?”
Jack: “Sometimes. But sometimes excess is the only honest prayer. When you’ve seen the void, you toast to it.”
Jeeny: “You think dying broke means dying brave?”
Jack: “Not broke. Empty. There’s a difference. Broke means nothing left to spend. Empty means you gave everything away.”

Host:
A long pause settled, filled by the low murmur of rain on the roof and the soft creak of leather booths. Jeeny looked down, her fingers tracing the edge of her glass. Her voice softened.

Jeeny: “You know, my father lived by the opposite rule. Saved every penny, denied himself joy for security. When he died, he left enough for comfort — for everyone but himself.”
Jack: “And did that make him happy?”
Jeeny: [shaking her head] “No. It made him afraid to stop working. As if rest was debt.”
Jack: “That’s the tragedy, isn’t it? We measure worth by what we keep, not what we give.”
Jeeny: “And yet, generosity isn’t a guarantee of peace either.”
Jack: “True. But neither is caution. You can die safe and still be a failure.”
Jeeny: “Flynn would call that a tragedy.”
Jack: “Flynn would call that Tuesday.”

Host:
The bar door opened briefly, letting in a gust of wet air and the scent of rain-soaked streets. A stranger walked in, shook off his coat, and ordered something strong. Life went on — indifferent, rhythmic, eternal.

Jack leaned forward, lowering his voice.

Jack: “You know what I think Flynn really meant? He wasn’t talking about money. He was talking about risk. That life only pays in experience. And if you die with any of it left unspent, you’ve failed the contract.”
Jeeny: “But some people find meaning in restraint.”
Jack: “Maybe. But restraint is just fear with good manners.”
Jeeny: “And recklessness is just fear pretending to dance.”
Jack: [laughs] “Touché. You always manage to moralize my mischief.”
Jeeny: “Someone has to.”
Jack: “But tell me, Jeeny — do you really think moderation ever made anyone rememberable?”
Jeeny: “Maybe not. But it kept them alive long enough to matter.”

Host:
The music changed, slower now — a melancholy piano weaving through the quiet. Jeeny’s eyes softened, and Jack looked out the window, watching the city shimmer through rain.

Jeeny: “You know, what scares me isn’t dying with money left. It’s dying with regret. The what-ifs, the never-dids.”
Jack: “Exactly. That’s what Flynn meant. That living safely is a slow suicide.”
Jeeny: “But there’s a fine line between living fully and destroying yourself in the process.”
Jack: “Maybe destruction is the price of depth.”
Jeeny: “Or the excuse for carelessness.”
Jack: “Maybe both. Every artist, every lover, every dreamer burns a little of themselves to prove they were real.”
Jeeny: “So, you admire the burn?”
Jack: “I admire the flame that knows it’s finite — and still burns anyway.”

Host:
The clock above the bar ticked softly, marking midnight. The bartender yawned, glancing at the two of them as if to remind them the night was running out. But neither moved. The moment had become too alive to end.

Jeeny: “You know, maybe the failure Flynn feared wasn’t dying rich — maybe it was dying untouched. Never ruined by love, never changed by risk.”
Jack: “That’s it. To live sterile is to die sterile. To hoard joy is to lose it.”
Jeeny: “So maybe we’re all meant to die a little poorer, as proof we spent our time.”
Jack: “Yes. The greatest inheritance isn’t money. It’s stories.”
Jeeny: “And scars.”
Jack: “Especially scars.”

Host:
Jeeny finally smiled, soft and tired, like someone who’d just remembered something she’d forgotten to forgive herself for. Jack raised his glass, the last of his whiskey catching the faint glow of the neon light.

Jack: “To Errol Flynn — the man who died broke but rich.”
Jeeny: [raising her glass] “And to every fool who dares to live like the ending’s already written.”
Jack: “Because it is — and that’s why it’s beautiful.”
Jeeny: “So, tell me, Jack — what would you want left when you die?”
Jack: [after a long pause] “Nothing but proof that I gave it all away.”

Host:
The bar fell silent, except for the rain outside and the echo of their laughter dissolving into it. The neon sign flickered one last time, reflecting in the window — red, gold, fading — like the heartbeat of a story that refused to close gently.

And in that fading light,
the truth of Errol Flynn’s words shimmered —

that life’s measure is not in what we preserve,
but in what we pour out.

That to die with nothing left
is to prove you lived with nothing withheld.

For money fades, fame erodes,
but passion — the reckless expenditure of self —
is the only true wealth that leaves no remainder.

So spend it all.
Love without ledger,
dream without deposit,
risk without refund.

And when the final curtain falls,
leave not ten thousand unspent,
but a legacy made of motion, laughter, and fire —

the kind of riches
that die with you,
and yet
keep the world
warm.