Judgment comes from experience - and experience comes from bad

Host:
The afternoon sun slanted through the office blinds, slicing the room into bars of light and shadow. The faint hum of computers, the distant sound of city traffic, and the quiet tap of rain against the window all mixed into a kind of rhythmic stillness. Papers were scattered across the mahogany desk, and the smell of burnt coffee hung in the air — the aroma of deadlines and bad decisions.

Jack sat behind the desk, coat off, tie loosened, a cigarette unlit between his fingers. His eyes, those sharp grey mirrors, stared at the numbers glowing on the screen — profits and losses, success and failure measured in percentages.

Across from him, Jeeny sat cross-legged on the edge of the couch, her hair loose, her expression calm but alert. She held a notebook in her lap, tapping it lightly with a pen, as if waiting for the right question to drop from the ceiling.

Jeeny: [softly] “Walter Wriston once said — ‘Judgment comes from experience, and experience comes from bad judgment.’”
Jack: [half-smiling] “So he’s saying failure’s the tuition fee for wisdom.”
Jeeny: “Exactly.”
Jack: “Then I should have a Ph.D. by now.”
Jeeny: [laughing] “You might. But have you actually learned anything?”
Jack: [shrugs] “That depends. If learning means not making the same mistake twice, then yes. If it means not making mistakes at all, then no one’s qualified.”

Host:
The room filled with the faint sound of rain growing heavier, the rhythm of it echoing against the glass like quiet applause for the conversation. Jeeny leaned forward, eyes locked on him — searching, questioning, pulling the thread of truth.

Jeeny: “So what’s your worst bad judgment?”
Jack: [smirking] “You mean today or this decade?”
Jeeny: “Let’s start small.”
Jack: [looking out the window] “I trusted that hard work would fix everything. Turns out, sometimes it just wears you down faster.”
Jeeny: “That’s not bad judgment, Jack. That’s hope misplaced.”
Jack: [sighing] “Hope and delusion wear the same coat until the bill comes due.”

Host:
A flicker of lightning lit the skyline, reflecting off the office glass. The city below glowed — a thousand lives, each pulsing with its own mistakes, its own small triumphs. Jeeny tilted her head, her voice quieter now, more deliberate.

Jeeny: “You know, experience isn’t just what happens to you — it’s what you do with what happens. Wriston meant that bad judgment isn’t a curse. It’s the forge.”
Jack: [raising an eyebrow] “So failure’s holy now?”
Jeeny: “Not holy. Human. Look at Edison — ten thousand failed attempts before one light bulb lit. Or Mandela — twenty-seven years of imprisonment before forgiveness became his revolution.”
Jack: [grinning faintly] “You’re comparing corporate blunders to revolutions?”
Jeeny: “I’m comparing the soul’s journey. We all start in ignorance and end, if we’re lucky, in grace.”

Host:
Jack chuckled softly, the sound dry but not cold. He set the cigarette down, fingers tracing the edge of the desk — the motion of someone wrestling with agreement but not yet surrender.

Jack: “You ever notice how society only celebrates the success, not the scar that made it possible? Everyone quotes success stories but skips the bad chapters.”
Jeeny: “Because scars make people uncomfortable. They remind us that perfection’s a performance.”
Jack: “And failure’s the backstage pass.”
Jeeny: [smiling] “Exactly.”

Host:
The rain softened, like a curtain falling between scenes. The light dimmed, the office taking on that late-hour hue where truth sounds easier but hits harder.

Jack: “You know what bothers me about that quote? It assumes we learn. But some people just keep making the same bad choices, calling it experience.”
Jeeny: “That’s not experience, that’s repetition. True experience transforms. It hurts, it humbles, it cleans you out.”
Jack: [leaning back, voice low] “You sound like a priest.”
Jeeny: [smiling slightly] “No, just someone who’s failed gracefully.”
Jack: “There’s such a thing?”
Jeeny: “Of course. Failure isn’t falling — it’s refusing to stand up again. Bad judgment is forgivable. Cowardice isn’t.”

Host:
Thunder rolled faintly, echoing off the tall buildings. Jeeny’s eyes softened, her pen stilled in her hand. There was something like understanding — not pity — in her expression.

Jeeny: “Tell me something, Jack. What did your last failure teach you?”
Jack: [after a pause] “That being right isn’t the same as being wise.”
Jeeny: [nodding slowly] “That’s a start.”
Jack: [quietly] “And that my arrogance cost me a friend.”
Jeeny: “Loss is often the tuition for humility.”
Jack: “And humility’s the degree we never brag about.”

Host:
The sound of the rain faded into a mist, the world outside settling into stillness. The clock on the wall ticked louder, marking time as both wound and salve.

Jeeny: “You know, Wriston understood something most leaders forget — that experience isn’t a list of accomplishments. It’s a record of recoveries.”
Jack: “Recoveries?”
Jeeny: “Yes. Each mistake is a fall; each insight, a resurrection.”
Jack: [half-smiling] “Then I must be on my fifth resurrection.”
Jeeny: “Then you’re halfway to sainthood.”
Jack: [laughs] “Hardly. Saints don’t swear at spreadsheets.”
Jeeny: [smiling back] “No, but they do learn patience from them.”

Host:
The lights flickered, reflecting the rhythm of the storm easing beyond the window. Jack leaned forward, elbows on the desk, the hint of something sincere in his tone now.

Jack: “Maybe you’re right. Maybe judgment’s not about avoiding mistakes — it’s about owning them. Knowing when to walk away, when to apologize, when to change.”
Jeeny: “That’s the heart of it. Bad judgment teaches empathy — the hardest kind of intelligence.”
Jack: “Empathy? From failure?”
Jeeny: “Yes. Once you’ve been broken, you understand the fragile. You stop judging others’ cracks.”
Jack: [quietly] “And start seeing your own.”

Host:
The silence that followed was heavy but kind. The rain had stopped. The air felt cleaner, the light softer, as if forgiveness had seeped through the walls.

Jeeny: “You know, I think that’s what Wriston meant. Judgment doesn’t come from perfection — it comes from surviving imperfection.”
Jack: “From failing and trying again.”
Jeeny: “From falling and remembering the ground.”
Jack: [nodding] “And maybe that’s why experience costs so much. Not in money — in pride.”
Jeeny: “Pride’s always the down payment for wisdom.”

Host:
Jack stood, walking to the window, watching the city glisten beneath the last drops of rain. The streetlights shimmered on the wet pavement like tiny constellations of consequence and redemption.

Jack: [softly] “Maybe all my bad judgment wasn’t wasted after all.”
Jeeny: “It never is, if it changes you.”
Jack: [turning toward her] “And if it doesn’t?”
Jeeny: “Then the universe will send you the same lesson again — louder this time.”
Jack: [smirking] “Cruel teacher.”
Jeeny: [smiling gently] “Patient one.”

Host:
The clock ticked once more, and in the hush that followed, both seemed to understand that failure, like rain, washes more than it ruins.

The storm outside had passed, but inside, something had cleared as well — not resolution, but recognition.

And as the lights of the city blinked against the wet glass, the truth of Walter Wriston’s words shimmered between them:

that wisdom is never inherited — it’s earned in mistakes, tested in humility, and proven in time.

That every scar is a lesson written in flesh,
and every bad judgment, a silent teacher
whispering: “Fall again — but fall forward.”