Only in our failures are we absolutely alone. Only in the pursuit

Host: The bar was nearly empty, the neon sign outside flickering like a heartbeat running out of rhythm. The air was thick with smoke and old jazz, and the bartender had long stopped pretending to clean the same glass he’d been holding for ten minutes. It was that hour when laughter from the earlier crowd had died down into murmurs, and the world itself seemed to pause between regret and fatigue.

Jack sat at the far end of the counter, his sleeves rolled up, his grey eyes heavy but awake — the kind of awake that comes not from energy, but from refusal to sleep. Jeeny was beside him, her hair tied loosely, a small notebook open before her. The cigarette smoke between them twisted like thought made visible.

On the bar, someone had left a dog-eared book. A quote was underlined in blue ink:

"Only in our failures are we absolutely alone. Only in the pursuit of failure can a person really be free. Losers may be the avant-garde of the modern age." — Sheila Heti.

The neon light above the words flickered, as if to emphasize them, a quiet pulse of irony and truth.

Jeeny: (softly) You ever think about that — being free through failure? It’s such a strange idea, isn’t it? That losing could be the only honest way to live.

Jack: (half-smiles) Strange, yeah. But not wrong. Success has too many witnesses. Failure’s private — and privacy is the only real freedom left.

Jeeny: (tilts her head) That’s bleak, even for you.

Jack: (shrugs) Maybe. But think about it. When you succeed, everyone owns a piece of you. The world congratulates you, defines you, packages you. When you fail — that’s yours alone. No one wants to claim it.

Host: A glass clinked somewhere behind the counter, and the sound echoed in the quiet room. The light from the neon sign painted their faces in alternating shades of blue and red, like they were sitting in a confession booth made of light.

Jeeny: (sighs) But doesn’t that sound lonely to you? This idea of being “free” only when everything falls apart?

Jack: Loneliness isn’t always the enemy. Some things can only be built in silence. Failure strips away illusion. It’s like — it burns the house down so you can finally see the sky.

Jeeny: (smiles faintly) And what if there’s nothing in the sky but more emptiness?

Jack: Then at least it’s honest emptiness. I’ll take that over the artificial comfort of applause any day.

Host: The bartender turned down the music, leaving only the crackle of an old record. Jeeny looked at Jack, the glow from her notebook catching her eyes, which held both warmth and disbelief.

Jeeny: You know, you sound like all those artists who call their pain “freedom” just to make it bearable.

Jack: (laughs quietly) Maybe. But at least they’re not lying about the price.

Jeeny: Still — “losers as the avant-garde”? That’s a brutal way of saying humanity’s best ideas come from despair.

Jack: (takes a sip) But isn’t that true? The ones who fail — they’re the ones who ask better questions. They’re not trying to protect a throne, just trying to understand why they fell.

Jeeny: (pensively) Failure as philosophy. You almost make it sound noble.

Jack: Not noble. Just necessary. Success teaches repetition. Failure forces invention.

Host: The rain began to fall outside, soft at first, then heavier, beating against the windows like applause from ghosts. The smoke curled upwards, and the air grew dense — like an idea too large for one room.

Jeeny: You know, I once worked with a painter who destroyed every canvas he made. Every single one. Said that “to finish” something meant “to limit it.” He called that failure his way of staying free.

Jack: (grinning) See? That’s exactly it. He wasn’t making paintings — he was making permission.

Jeeny: Permission for what?

Jack: To exist without conclusion. That’s the truest kind of rebellion.

Jeeny: (pauses) So you think the point of art — of life — is to never finish?

Jack: To never freeze. Completion is a kind of death, Jeeny. People chase success because they think it’ll complete them, but completion is just another word for stillness.

Jeeny: (whispers) And stillness scares you.

Jack: (after a beat) It should scare everyone who’s still alive.

Host: The light from the neon sign outside briefly brightened, casting their faces into sharp contrast — hers soft with empathy, his etched with conviction.

Jeeny: (softly) But don’t you think freedom can exist without losing? I mean, what about joy, or love, or creating something beautiful just for the sake of it?

Jack: (leans forward) Joy can’t teach you anything lasting. Love, maybe — but even love ends in failure. It’s fragile by design. Every connection breaks eventually, one way or another.

Jeeny: (quietly) That’s a cruel way to see the world.

Jack: (shrugs) Maybe it’s clear-eyed. The world’s built on ruins, Jeeny. We just pretend the ruins are foundations.

Host: She looked at him, the light flickering across her cheekbones, her expression hovering somewhere between anger and pity. The bar’s old clock ticked, heavy, echoing like a heartbeat that had slowed but refused to stop.

Jeeny: (firmly) You know, Jack, I think people fear failure not because of pride — but because of abandonment. Because when you fail, the world leaves you. You’re right — you’re alone. But maybe that’s why failure hurts. Because it reminds us how badly we need each other.

Jack: (studying her) So you think connection matters more than freedom.

Jeeny: I think freedom without connection isn’t freedom. It’s exile.

Jack: (smiles faintly) You’re the only person I know who could make exile sound poetic.

Jeeny: (leans closer) And you’re the only person who could make despair sound like a career.

Host: They both laughed, but it wasn’t the easy kind — it was laughter that cracked, revealing something raw beneath. The rain outside had softened to a whisper, blurring the world into watercolor.

Jack: (after a pause) You ever notice that all revolutions start with people who’ve failed? The rejected, the fired, the broken — they’re the ones who tear down empires. Maybe Heti’s right. Maybe losers are the avant-garde. They see the cracks before the walls collapse.

Jeeny: (nods slowly) Maybe. But they also bleed first. And sometimes, the world never thanks them for it.

Jack: (quietly) That’s why they’re free. Because they stopped waiting for thanks.

Jeeny: (softly) Or maybe because they finally realized that freedom and belonging don’t live in the same house.

Host: The fire in his eyes dimmed slightly. The truth of her words settled between them — not an argument, but a recognition. The bar was almost dark now; even the neon sign outside had begun to die, its final flickers weak and irregular.

Jeeny: You know, I used to think failure was the end of the story. Now I think it’s the place where honesty begins.

Jack: (nods) Yeah. Failure’s the point where you finally stop performing. There’s no audience left to please. Just the mirror.

Jeeny: And the mirror doesn’t lie.

Jack: (half-smiles) It doesn’t have to. You’re already the lie and the truth in one reflection.

Host: The bartender began to close up. Jack and Jeeny stayed where they were, not speaking now — both staring at the same half-empty glass between them, like it held the last drop of the night’s philosophy.

Jeeny: (softly) Maybe failure isn’t freedom because it isolates us. Maybe it’s freedom because it strips us of illusion — and that’s the only time we can see clearly enough to choose what comes next.

Jack: (after a pause) And maybe choosing is the only real success.

Host: A faint smile touched both their faces. The rain had stopped. Outside, the streetlights flickered across puddles, turning failure itself into something luminous — broken pieces catching the light.

They stood, gathered their coats, and as they walked toward the door, the neon sign above the bar sputtered its final breath — one last pulse of red — before going completely dark.

And in that darkness, there was something like peace — the quiet understanding that failure, in its rawest form, wasn’t an ending at all,
but the moment a soul stops pretending and starts breathing.