I think you have to try and fail, because failure gets you closer

Host: The rain had been falling for hours — slow, deliberate, like the sky was rehearsing grief. In the corner of a nearly deserted coffee shop, the neon sign outside blinked a faint blue pulse across the wet windowpane, reflecting off half-empty cups and the steam rising between them. Jack sat hunched forward, elbows on the table, his hands wrapped around a chipped mug. Across from him, Jeeny watched him in silence — her eyes soft, curious, and just a little sad.

Somewhere in the background, an old radio hummed quietly — a jazz tune about time and the people it forgets.

Jack broke the silence.

Jack: (dryly) “Louis C.K. once said, ‘You have to try and fail, because failure gets you closer to what you’re good at.’ I think he’s half right.”

Jeeny: (raising an eyebrow) “Only half?”

Jack: “Yeah. Failure doesn’t get you closer to anything. It just tells you where you don’t belong. People love to romanticize failure — call it a teacher, a blessing in disguise. But it’s just loss, Jeeny. Loss dressed in philosophy.”

Host: The light flickered as a car passed outside, splashing through a puddle. The reflection of its headlights briefly illuminated Jack’s face — hard, tired, carved with the weight of unspoken regret.

Jeeny: “Maybe you’re remembering the wrong kind of failure, Jack. The kind that hurts but doesn’t teach. The kind that makes you stop instead of start again. But Louis wasn’t talking about that — he was talking about practice. About becoming.”

Jack: “Becoming what? The universe doesn’t hand out report cards for effort. You fail enough times, people stop believing in you — including yourself.”

Jeeny: “But you’re still here, aren’t you? Drinking bad coffee, quoting comedians like philosophers. Maybe failure didn’t kill you. Maybe it refined you.”

Host: A faint smile flickered at the corner of her mouth, but her eyes stayed serious. The air between them felt dense, as if every word had to fight through years of silence before being born.

Jack: “You ever wonder if we only say things like that because the truth’s too ugly? Because we can’t admit we wasted years chasing something we were never meant for?”

Jeeny: “You didn’t waste it. You lived it. Even mistakes are part of the map.”

Jack: “Yeah, well, mine looks like a maze drawn by a drunk god.”

Host: The rain tapped faster against the glass, like fingers impatient on a table. The sound filled the spaces their words left behind. Jeeny reached for her cup, blowing gently on the steam, her reflection merging with Jack’s in the window — two ghosts trying to make sense of what had already burned down.

Jeeny: “When I was twenty, I tried to be a painter. I failed — spectacularly. My lines were clumsy, my colors flat. But that failure pushed me to write. Paintings couldn’t hold what I needed to say, but words could. If I hadn’t failed, I’d still be chasing a silence that didn’t belong to me.”

Jack: “And what if you’d failed at writing too?”

Jeeny: (smiling) “Then I’d still be searching. Isn’t that what living is?”

Host: The lamp above them buzzed, flickered, then steadied — its faint yellow glow washing the table in soft light. Jack’s hands tightened around his mug. He didn’t answer right away. Outside, a child laughed in the distance — brief, bright, unguarded.

Jack: “You make it sound noble. Like all our broken attempts are just steps toward destiny. But some people fail forever. Look at Van Gogh — he died broke and mad.”

Jeeny: “And yet, Jack, his failure gave the world light. Every color he couldn’t sell became a part of history’s sky. You think that’s nothing?”

Jack: (scoffing) “That’s hindsight. Nobody sees the masterpiece when you’re still mixing the paint.”

Jeeny: “Then maybe the lesson is to keep mixing, even when no one’s watching.”

Host: The café door creaked open. A gust of wind swept in, carrying the smell of wet earth and city rain. Jack looked toward the doorway as if expecting someone to appear — an old friend, a ghost, a version of himself who hadn’t yet quit trying.

Jack: “You ever feel like you’re done learning from pain?”

Jeeny: “No one’s ever done. Pain’s the tutor that never clocks out.”

Jack: “Then why does it feel like failure teaches the same damn lesson — over and over?”

Jeeny: “Because you haven’t learned to listen to it yet.”

Host: The moment lingered. Jeeny’s words hung in the air, heavy but kind. Jack leaned back in his chair, his expression unreadable — somewhere between a grimace and a smile.

Jack: “So what you’re saying is, all my screw-ups are just cosmic breadcrumbs?”

Jeeny: “Exactly. Each one leading you closer to the thing that feels like home.”

Jack: “And if there is no home?”

Jeeny: “Then keep walking until one finds you.”

Host: The rain softened now, turning into a mist that blurred the streetlights outside. The neon sign flickered again — a heartbeat of blue and red against the night. Somewhere, a train horn sounded, deep and distant, like time itself exhaling.

Jack: “You ever think Louis C.K. was talking about himself? A man who failed, fell, and still got up to joke about it. Maybe that’s his point. You fail publicly enough times, you stop fearing it.”

Jeeny: “Yes. You fail enough, and fear loses its teeth. That’s when you start living honestly.”

Jack: “So failure’s freedom?”

Jeeny: “In disguise.”

Host: Jeeny’s voice was low but certain. The coffee shop was nearly empty now. A barista wiped the counter, humming softly. The clock on the wall ticked toward midnight — steady, indifferent.

Jack stared at the tabletop, tracing invisible circles with his finger — like drawing maps of things already lost.

Jack: “You know, when I was a kid, I wanted to be a pilot. Failed the test twice. Ended up in business school. Failed that too. Every wrong turn led me somewhere smaller — safer. And now, I sell things I don’t believe in to people who don’t need them.”

Jeeny: “But you’re here. Talking about it. That means the part of you that wanted to fly is still alive. It’s just waiting for you to remember the sky.”

Jack: (smirking) “Poetic as ever.”

Jeeny: “Someone has to be.”

Host: The rain finally stopped. The world outside was washed clean, the streetlights shimmering in newborn puddles. Jack looked out, his eyes softer now — a man standing at the edge of surrender, or maybe awakening.

Jack: “Maybe Louis was right, then. Failure doesn’t just show you what you’re bad at — it strips you down until what’s left is what you were always meant to be.”

Jeeny: “Exactly. You can’t find gold without burning through the dirt first.”

Jack: “So all this — the losses, the wrong turns — it’s just excavation?”

Jeeny: “Yes. You keep digging until the truth shines.”

Host: The first hint of dawn crept through the window, soft and silver. The city was waking — a bus rumbled somewhere distant, a street vendor pulled up his cart, and a pigeon landed on the ledge, shaking off the rain.

Jack: (quietly) “You ever get tired of believing in people like me?”

Jeeny: “No. Because watching someone find themselves after falling — that’s the closest thing to faith I know.”

Host: The neon sign went dark, leaving only the morning light — pale and forgiving. Jack smiled — small, uncertain, but real. He looked down at his cold coffee, then back at Jeeny.

Jack: “You know… maybe I’m not done trying.”

Jeeny: (smiling) “Then you’re already closer to what you’re good at.”

Host: Outside, the sky brightened, its gray giving way to faint blue. The last drops of rain clung to the window like tiny worlds — fragile, trembling, alive. Inside, two souls sat across from each other, the silence between them no longer heavy but full — full of something beginning again.

And as the city stirred awake, their laughter rose softly —
the sound of failure turning into flight.