How Can We Fail When We’re So Sincere?
An illustrated guide to failing earnestly while bastards prosper with applause
Wineglass Bay Beach, Freycinet National Park, Tasmania
There’s nothing quite like the unique, gut-churning injustice of failing when you’ve done everything right. When you’ve played fair. When you’ve believed – earnestly, foolishly, with the wide-eyed trust of a dog staring at a ball that will never be thrown – that sincerity counts for something. And yet.
And yet.
Failure. Not the noble, chin-up variety. The other kind. Spectacular. Undeniable. The kind that leaves you flat on your back, spread out like a fallen constellation that never quite made it to the sky, wondering if you’ve just been steamrolled by the universe’s least subtle metaphor.
There's no teachable moment, rather, it’s a cosmic piss-take. A reminder that life isn’t a journey or a test; it’s a trippy, looping vignette where meaning flickers in and out like bad reception and you’re the recurring character who keeps walking into the same glass door. Maybe you’re meant to evolve. Maybe you’re just meant to flinch more elegantly. Either way, the punchline lands, the lights stay on, and you’re still face-down in the dirt, waiting for someone to yell “cut” who never will.
Because sincerity should be a winning strategy, shouldn’t it? That’s what we were taught. Be honest, work hard, speak from the heart, and good things will come. It has all the right ingredients – integrity, passion and a touching naivety. If life worked the way we were told, sincerity would be a golden ticket. And yet, here I am, face-first in the dirt, watching the bastards collect their trophies while I try to work out where I went wrong. History – cold, unblinking, ruthlessly unsentimental – says otherwise.
The Long, Bloody History of Sincere Losers
History is overflowing with the noble, the earnest, the true believers who fought the good fight and ended up either dead, exiled, or – worst of all – reduced to a humiliating JPEG with the caption “This You?” circulating endlessly on Twitter while someone quote-tweets it with “bro thought he was him 💀.”
Watt Tyler, who thought kings would honour their word, only to get a dagger in the ribs for his troubles. Robespierre, the patron saint of overcommitted idealists, spent years perfecting the art of righteous execution before becoming one himself. Ed Miliband, whose fatal mistake wasn’t his policies but believing he could eat a bacon sandwich like a normal human. Turns out, you can have a heart of gold, a brain like a mainframe, and a vision for justice that’d make Desmond Tutu weep, but if you like like a dick when you eat, fuck off.
And then there’s Charles Fourier, a man so sincere he makes Milliband look like Machiavelli. Fourier dreamed of harmonious utopias built on mathematical formulas, passion-driven labour, and a future where the oceans would literally turn into lemonade. I mean, why not? If you’re going to be sincerely deluded, go big. Well, why not? If you’re going to be earnestly, unapologetically wrong, you might as well commit. Fourier’s utopias weren’t just ambitious, they were baroque fever dreams, laced with such conviction that when someone politely suggested the oceans might not, in fact, be on the verge of turning into lemonade, he didn’t flinch. He nodded, smiled and (probably) wrote a poem about non-repressive sublimation.
Which brings us to Charlie Brown.
Charlie Brown, The Eternal Loser
No one embodies the tragedy of sincerity quite like him. Poor bastard still thinks it works like that. Still thinks life is a game of just deserts and cosmic fairness. Still thinks Lucy won’t pull the football away. I almost envy him. Almost.
One of my all-time favourite Peanuts strips - 6 April 1963, for those playing along at home - nails it. Charlie Brown, fresh from a 184–0 humiliation says: “I don’t understand it… How can we lose when we’re so sincere?”
There it is: the great delusion. That sincerity is some kind of tactical advantage. That meaning well might cancel out total incompetence. As if the scoreboard gives a shit about your earnest little heart.
It isn’t. And it never has been. This is what makes Charlie Brown the perfect tragic figure – he never, ever learns. He kicks, she pulls the ball away, he lands flat on his arse. But he still gets up, still believes and still falls for it. Charlie Brown isn’t just a character; he’s a warning label slapped on the human condition. He is hope with a concussion. A cautionary tale with a round head and a permanent sense of impending doom. The fact that he still gets up? That’s either inspiring or proof that the man has suffered irreversible brain damage. Either way, I respect it.
Ask Me How I Know
You see, I don’t just observe the tragic fate of the sincere. I have lived it.
So, picture this: Boy likes girl (a LOT). Girl likes boy (and says so). Boy – poor, dumb, tragic bastard – sees an open door and sprints through it, heart in hand, like he’s been training for this moment his entire life. Finally, FINALLY, someone understands him! Sincerity is finally being rewarded! This is his great revolution! His Robespierre moment! The heavens are parting! The orchestra is swelling! His life is a third-act redemption arc in a coming-of-age film!
And then...
The camera zooms out. She is not experiencing a sweeping romantic epiphany. She is scanning the room like she’s just spotted the last chopper out of Saigon.
That’s the thing about sincerity – it doesn’t just make you vulnerable. It makes you predictable. It makes you exploitable. It makes you the poor idiot standing there, bomb in hand, while the clever ones tiptoe away whistling.
Meanwhile, the Bastards Keep Winning
While the earnest get publicly humiliated, history just keeps handing trophies to the insincere. The cunning. The ones who know when to smile, when to lie, and when to shake your hand while quietly emptying your pockets. The ones who walk away from the explosion, adjusting their tie while pointing at you and saying, “he did it.” The real lesson here? It’s not the best who win. It’s the best at getting away with it.
Take Front End Loader’s “How Can We Fail When We’re So Sincere?” Written in the early 2000s, in the golden, frothing months of post-9/11 imperial hubris, it’s a bitter, snarling takedown of America’s unwavering belief in its own goodness. The sheer, almost innocent confidence with which it marched into disaster after disaster, convinced that sincerity alone could substitute for a plan.
And if you need another case study, I present: Bono.
Bono is – by all available evidence – genuinely, deeply, painfully sincere. He wants to save the world. He really does. And yet. Somehow, he manages to make you root against his own humanitarian efforts. Somewhere along the way, sincerity curdled into something else – something preachy, self-important, and inescapable, like an aggressive street fundraiser that somehow has your home address.
The perfect example? That U2 album Apple forcibly downloaded onto everyone’s iPhone in 2014. A true, earnest, well-intentioned gift to humanity – met with the kind of global backlash normally reserved for war crimes. For a brief, shining moment, the entire planet was united – not in peace, not in goodwill, but in their shared and absolute hatred of Bono. It was so universally reviled that I’m pretty sure it’s the only thing people from every political ideology, religion, and tax bracket have ever agreed on.
Bono’s mistake wasn’t meaning well. It was assuming that people would appreciate the gesture – which is the same mistake every sincere loser in history has made, from Fourier to Miliband to, yes, the boy (I forget his name, it started with a “K”) who liked the girl.
So, What’s The Answer?
Do we abandon sincerity? Harden our hearts? Become the knife-wielders instead of the knife-receivers?
Maybe. It would certainly be easier.
But let’s be honest. Some of us are too far gone. We’re Charlie Browns through and through. We will always line up for the next kick. We will always believe – however foolishly – that this time might be different.
And honestly? That’s fine.
Because here’s the real choice.
Some people fail because they knew it was a game and played it badly.
Some people fail because they refuse to play at all.
But sometimes – just sometimes – sincerity wins. Not in the way you expect. Not in the way you want. But in some ridiculous, accidental, loophole-riddled way that almost makes it feel worth it. Maybe some idiot kicks the football, and by sheer dumb luck, it goes through the posts. Maybe Charlie Brown wakes up one day and Lucy gets distracted just long enough for him to finally land a clean boot. Who knows? Stranger things have happened.
And maybe – just maybe – that boy didn’t get the girl.
Not that girl, anyway. She was a lesson – the final, glorious, humiliating, headlong crash that taught him to slow the hell down. To read the room. To know when to sprint and when to lean casually against the metaphorical doorframe like he’s definitely not planning to say something mortifying.
And a few years down the track? He found another girl. A better one. One who liked his sincerity but didn’t bolt the moment he went Full Romantic Idiot. He found the balance – enough cool distance to avoid the Saigon flashbacks, but enough sincerity to actually mean something.
Which is all to say: Sincerity isn’t doomed. It just has to know when to shut the fuck up for a second, give a coy smile and let your fringe flop over those big beautiful eyes and don’t look quite so desperate.