Mistakes are the best teachers. One does not learn from success.

Host: The evening sky was muted bronze, the kind of light that carries the weight of both endings and understanding. Through the glass walls of a quiet office, the city shimmered below — distant, mechanical, alive.

The floor was scattered with charts, printouts, and coffee cups, casualties of another long night of postmortem reflection. The whiteboard was covered in equations, arrows, and one circled phrase:

“Mistakes are the best teachers. One does not learn from success. It is desirable to learn vicariously from other people's failures, but it gets much more firmly seared in when they are your own.”
— Mohnish Pabrai

Jack sat near the window, sleeves rolled up, the remnants of tension still on his face. Jeeny stood at the whiteboard, her hair loose, holding a marker like a conductor holding a wand. The air between them pulsed with that strange electricity that only comes after losing something valuable — money, time, certainty, or pride.

Jeeny: “So that’s it, then. The trade failed.”

Jack: “Spectacularly.”

Jeeny: “And yet you look like someone who just watched a meteor crash and decided it was beautiful.”

Jack: “Because it was. Painful — but instructive.”

Host: The city lights trembled across Jack’s eyes, flickers of orange and white — the reflections of lessons learned the hard way.

Jeeny: “So you’ve joined the church of Pabrai, then? Praise be to the holy mistake?”

Jack: “Something like that. Success flatters your judgment. Failure audits it.”

Jeeny: “That’s poetic. And probably expensive.”

Jack: “Very.”

Host: Jeeny leaned against the board, arms folded, studying him with the patience of someone who’d seen many men baptized by failure but not all redeemed by it.

Jeeny: “You think you could have learned this lesson by watching someone else screw up instead?”

Jack: “I thought I could. But second-hand pain is like reading about fire. You don’t know it until it burns you.”

Jeeny: “And now you know?”

Jack: “Now I respect the burn.”

Host: A faint hum of the air conditioner filled the space — a quiet metronome for reflection.

Jeeny: “What did it teach you this time?”

Jack: “That intelligence and wisdom are different currencies. Intelligence gets you into trades; wisdom tells you when to walk away.”

Jeeny: “So wisdom costs you your comfort.”

Jack: “And comfort costs you growth.”

Host: She smiled — not with triumph, but with recognition. The kind of smile that comes when the truth arrives too late to save you but just in time to transform you.

Jeeny: “You know, Mohnish Pabrai built his career on that idea. He calls mistakes his tuition fees. Says the market is the world’s most honest teacher — it doesn’t lie, doesn’t flatter, and never hands out participation trophies.”

Jack: “Yeah. And he’s right. Every failure gives you a scar — and scars don’t fade easily. That’s why you remember the lesson.”

Jeeny: “So tell me, Professor Scarred — what did this one cost you?”

Jack: “A quarter-million. And an illusion.”

Jeeny: “Which illusion?”

Jack: “That I was smarter than randomness.”

Host: The silence that followed wasn’t awkward — it was reverent, as though both were bowing to the invisible altar of truth that failure had built between them.

Jeeny: “You know, the irony is, people chase success thinking it’ll make them secure. But it’s the opposite. Success sedates. Failure sharpens.”

Jack: “You sound like you’ve had your share of sharpening.”

Jeeny: “Enough to know the difference between pain and progress.”

Jack: “Sometimes they feel identical.”

Jeeny: “That’s how you know it’s working.”

Host: The lights dimmed automatically, a quiet reminder that it was well past midnight. The world outside still pulsed with motion, but up here, reflection had replaced ambition.

Jack: “You think it’s true — that we don’t learn from success at all?”

Jeeny: “Success teaches you what worked. Failure teaches you why.”

Jack: “And ‘why’ is the more expensive word.”

Jeeny: “But it’s the only one that builds resilience.”

Host: Jeeny crossed the room, picked up one of the papers from the table — a printout of the losing trade. She held it up to the light.

Jeeny: “You’ll keep this, won’t you?”

Jack: “As a relic?”

Jeeny: “As a teacher.”

Jack: “I already have too many teachers.”

Jeeny: “Then you’re finally becoming wise.”

Host: She dropped the paper back onto the pile, and for a moment, it fluttered like a dying moth before resting — silent, harmless, spent.

Jack: “You know what I’ve realized, Jeeny? Every time I’ve succeeded, I’ve moved forward. But every time I’ve failed, I’ve evolved.”

Jeeny: “There’s the real tuition speaking.”

Jack: “Pabrai called it searing — the kind of learning that brands itself into you. He’s right. This one’s burned in deep.”

Jeeny: “Good. Because burns fade, but the nerve remembers.”

Host: The faint sound of rain began to patter against the window — slow, cleansing, rhythmic. The city blurred beyond the glass, as if the universe itself were wiping the slate clean.

Jeeny: “So, what’s next?”

Jack: “Another risk. Smaller maybe. Smarter definitely.”

Jeeny: “You think you’ll fail again?”

Jack: “I hope so.”

Jeeny: “That’s... deranged.”

Jack: “No. That’s disciplined.”

Host: Jeeny laughed softly, her breath fogging the window for a moment — a brief ghost of warmth against the cool night.

Jeeny: “You know, there’s something kind of noble about that. The idea that wisdom is born not from triumph, but from error.”

Jack: “That’s all wisdom ever is — the scar tissue of the mind.”

Jeeny: “And here I thought wisdom came from books.”

Jack: “Books are other people’s scars. You just hope their pain saves you a little of your own.”

Host: The clock ticked softly. The rain grew steadier. The city below became a watercolor of reflections.

Jeeny: “You think you’ll ever stop fearing failure?”

Jack: “No. But I’ll stop worshipping success.”

Jeeny: “Then you’re already ahead of most people.”

Host: She turned off the lights. The room dimmed to the glow of monitors and the faint shimmer of wet glass. Jack stayed where he was — still, contemplative, but lighter somehow, like a man who’d made peace with the ashes of his ambition.

The night outside stretched infinite and forgiving, whispering with the soft rhythm of rain.

And on the whiteboard, Freya Stark’s chalked quote seemed to breathe under the dim light — not as advice, but as law:

Mistakes are the best teachers — because truth demands tuition.

And as the camera pulled back — the two of them silhouettes against a skyline of imperfect brilliance — one could almost hear the quiet, unspoken revelation settle into the air:

Success rewards you with comfort.
Failure rewards you with consciousness.