The Confidence of Oscar Wilde

Applying the power of wit to the right times and places, seeing what it can and cannot do, and fiddling with the dials until the repartee is right where you want it to be.

We’ve all been in tha situation where we need to say something clever but innocuous; something smart enough to show some intelligence without showing off; something funny but not a joke. What we need in that moment is wit–that sparkling combination of charm, humor, confidence, and, most of all, the right words at the right time.

Elements of Wit: Mastering the Art of Being Interesting is an engaging book that brings together the greatest wits of our time, and previous ones from Oscar Wilde to Nora Ephron, Winston Churchill to Christopher Hitchens, Mae West to Louis CK, and many in between. Here is the confidence of Oscar Wilde.

What you’ve thus far done is constructed a self that’s ready to see some cocktail-party action. Now you need to put that self out there. And how do you put yourself out there? With conficence.

The two prongs of confidence

Are you good at a certain thing, and do you believe you’re good at it?

You might think it only matters that you are objectively good, but of course, that alone is not going to make you challenge yourself. Ideally, then, you might be quantifiably very good at something and then believe you are even slightly better, because who’s to say you can’t get better in the process of rising to the occasion?

Oscar Wilde was clearly very good at being witty, and was quite aware that he was good at it. But, as everyone familiar with even the broad strokes of his life knows, he was far too confident in his abilities. The fact that his biography had such a dramatic arc has certainly helped burnish his legend, and he saw it coming: Late in life in a letter he rechristened himself “St. Oscar of Oxford, Poet and Martyr.’ Before that, his brash confidence in his wit made him the brightest star of his age.

But was he any good?

Many artists die in obscurity and achieve fame posthumously; the luckier ones become famous in their lifetime and more so thereafter. Oscar Wilde managed to do all of the above. In his life, he sumbolized the decadent movement in fin de siècle England; his homosexuality was a public secret that added to his infamy but didn’t exlipse it (at least, not until it destroyed his career). After his death, he beccame a dort of folk hero: gay, Irish, well-spoken and the author of at least one undiminished masterpiece, The Importance of Being Earnest, and several essays that still sizzle off the page.

But it must be said: He wasn’t always that good. A dive into his collected maxims shows an almost childish formula at play. Furthermore, it’s arguable that he doesn’t satisfy either half of our definition of wit as spontaneous creativity. His major works are certainly original, but elsewhere is his oeuvre you’ll find blatant rip-offs of both his fellow poets and his own work.

So why, if we’ve decided that Oscar Wild as he is known today is more often than not a cliché of wit, are we going to forgive him and hold him aloft as a model to be emulated?

LADDY BRACKNELL: (Pulls out her watch.) Come dear. (Gwendolyn rises.) We have already missed five, if not six, trains. To miss any more might expose us to comment on the platform.

The world today is as full of Lady Bracknells as it was in Wilde’s time, if not more so. To be a Bracknell is to be entirely concerned with the perceived propriety of things and distinctly unbothered by the way things actually are.

Wilde knew that people might sputter and gasp, but he knew that alone couldn’t hurt him. As he declared to a hungry pack of newspaper reporters on the occasion of his visit to America, “The ridicule which aesthetes have been subjected to is the only way of blind unhappy souls who cannot find the way to beauty.”

Oscar Wilde was all about being true to one’s self, mainly because he saw no other way to be. “All imitation in morals and in life is wrong,” he wrote. And once you had that truth, you might as well be vocal about it.

Complement Elements of Wit: Mastering the Art of Being Interesting with Be biased in favor of taking action. Broadcaster Claire Shipman, author of The Confidence Code: The Science and Art of Self-Assurance—What Women Should Know, explains the positive aspects of allowing confidence to grow within yourself. The best way to do this is to erase any fears that keep you from leaping toward professional and personal challenges.