If at first you don't succeed... so much for skydiving.

“If at first you don’t succeed... so much for skydiving.” — in this single line, Henny Youngman, master of sharp wit and timeless humor, captures a paradox that humbles the human spirit. Beneath the laughter his words provoke lies a profound lesson about the limits of persistence, the wisdom of discernment, and the fine line between courage and folly. For though perseverance is noble, not every battle is meant to be fought twice, and not every failure allows for a second attempt.

In the ancient world, philosophers praised endurance — the virtue of rising again after defeat. Yet even they knew that wisdom must walk hand in hand with bravery. Youngman’s humor hides an old truth: while persistence is sacred, there are realms where failure is final, and wisdom lies in knowing the difference. His joke about skydiving turns the common motivational saying on its head, reminding us that life is not merely about trying again, but about understanding when and how to try.

The ancients would have smiled at this jest, for they too cloaked wisdom in laughter. Think of Diogenes the Cynic, who mocked the arrogance of men by living in a barrel, teaching truth through absurdity. So too does Youngman’s line awaken insight through irony. In the realm of skydiving, failure cannot be followed by perseverance — it can only be followed by silence. Thus he invites us to reflect: there are pursuits where the cost of error demands respect, where enthusiasm must bow before preparation, and where life itself is the wager.

History offers its own examples. Consider the story of Otto Lilienthal, the German pioneer known as the “Glider King.” In the late 19th century, he built machines to imitate the flight of birds, risking his life again and again in pursuit of the sky. His courage changed the course of aviation — yet one fateful crash in 1896 ended his life. His final words were, “Sacrifices must be made.” He did not lack perseverance; he lacked what Youngman’s humor gently implies — the balance between ambition and prudence.

In another sense, this quote speaks to humility before the laws of nature. The earth does not forgive arrogance, and gravity is a teacher that never compromises. The wise do not challenge nature recklessly, but seek harmony with it. So in every great endeavor — be it love, invention, or exploration — there must be a reverence for the forces greater than ourselves. Youngman, through jest, whispers a warning: not all risks are worthy, and not all failures are survivable.

And yet, beneath the caution, there is no call to cowardice. The spirit of his words reminds us that laughter is the shield of the brave, that even in the face of danger, one can smile at the absurdity of human striving. To laugh at the risk of falling is not to deny fear, but to master it. Humor becomes wisdom’s twin — teaching that while we must not tempt fate blindly, we must also not live in dread of it.

The lesson is clear: perseverance is a virtue, but discernment is a greater one. Know when to rise again, and know when not to fall at all. In every pursuit, measure your courage against the weight of consequence. Prepare, learn, and respect the boundaries that nature — and life — have drawn. For wisdom is not in endless trying, but in rightly trying.

So, to those who hear these words in the centuries to come: chase the winds of your destiny, but pack your parachute well. Laugh when the challenge seems absurd, but never forget that laughter itself is born of awareness. As Henny Youngman reminds us, some failures leave no second chance — and in knowing this, we do not lose heart, but gain wisdom.