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Leadership Quote by A. J. Liebling

"If you just try long enough and hard enough, you can always manage to boot yourself in the posterior"

About this Quote

The joke lands because it takes the peppy American gospel of self-improvement and turns it into slapstick self-harm. Liebling borrows the cadences of motivational uplift - "try long enough and hard enough" - then yanks the rug with a grotesquely practical outcome: not success, not virtue, just the satisfaction of proving you can injure your own dignity through sheer persistence. It's optimism rewritten as masochism.

Liebling, a journalist who made a career out of puncturing pomposity, aims this at the kind of moral bookkeeping that treats effort as its own proof. The subtext is that willpower isn't inherently noble; it's merely powerful, and power applied blindly can be disastrous. You can work tirelessly at the wrong thing, cling to a bad plan with heroic stamina, or double down on an ego-saving mistake until it becomes a full-body bruise. The "posterior" keeps it genteel enough for print while still evoking the childish humiliation of getting caught out by your own grand ideas.

Context matters: mid-century America was thick with bootstraps mythology, corporate hustle, and a faith that grit solves structural problems. Liebling's wisecrack functions as an inoculation against that national sermon. It also reads as newsroom wisdom: deadlines, rivalries, and overconfidence make self-sabotage less a tragedy than a professional sport. The line isn't anti-effort; it's anti-self-deception. Persistence, Liebling suggests, is not a compass. Without judgment, it's just a longer route to kicking yourself.

Quote Details

TopicWitty One-Liners
SourceHelp us find the source
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APA Style (7th ed.)
Liebling, A. J. (2026, January 17). If you just try long enough and hard enough, you can always manage to boot yourself in the posterior. FixQuotes. https://fixquotes.com/quotes/if-you-just-try-long-enough-and-hard-enough-you-37079/

Chicago Style
Liebling, A. J. "If you just try long enough and hard enough, you can always manage to boot yourself in the posterior." FixQuotes. January 17, 2026. https://fixquotes.com/quotes/if-you-just-try-long-enough-and-hard-enough-you-37079/.

MLA Style (9th ed.)
"If you just try long enough and hard enough, you can always manage to boot yourself in the posterior." FixQuotes, 17 Jan. 2026, https://fixquotes.com/quotes/if-you-just-try-long-enough-and-hard-enough-you-37079/. Accessed 12 Feb. 2026.

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About the Author

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A. J. Liebling (October 18, 1904 - December 28, 1963) was a Journalist from USA.

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