Quote of the Day: Steven Wright on Humor & Life

We live in a feed where failure is frictionless: delete the post, rerun the prompt, rebrand the side hustle, and call it “iteration.” In that soft, rewindable world, perseverance becomes a default setting. Then a deadpan line yanks us back to physics and consequence: “If at first you don’t succeed, then skydiving definitely isn’t for you.”

The joke works because it weaponizes a cliché. “Try, try again” is comforting precisely because it pretends context doesn’t matter, because it treats every setback like a harmless draft. Wright replaces the motivational poster with a harness, a parachute, and a one-shot test of reality. The laugh arrives at the instant we realize how often we apply the same blanket advice to situations that don’t grant do-overs.

There’s a serious ethic hiding inside the punchline: distinguish grit from negligence. Persistence is noble when feedback is frequent and failure is survivable, learning a language, building a product, practicing resilience. It’s reckless when error is irreversible or costs other people their safety: medicine, aviation, cybersecurity, financial leverage. The point isn’t “don’t try”; it’s “prepare, simulate, and lower the stakes before you bet the whole body.” Optimism needs guardrails.

Steven Wright has built a career on taking familiar sayings literally until they fracture, revealing the hidden assumptions inside our everyday language. His deadpan style makes the logic feel cold, right up until you notice it’s also clarifying.

Whether you’re launching a project, switching careers, or trusting AI to move fast and break things, apply the line as a filter: where can you safely iterate, and where must you be competent before you leap? Choose courage, but price the consequences first.