The Art of Having Nothing to Lose

“The Trickster is not a trickster by nature. He is a trickster by necessity.” – Malcolm Gladwell

Governing the precept that the self is masks all the way down perceiving delusions all the way up, it stands to reason that one of those “masks” would embolden the self to question all delusions and break all masks. Indeed, one of those masks should embolden the self to the extent that it thinks it has nothing to lose. That mask is the mask of the trickster.

When a person dons the mask of the trickster, they become the personification of a trickster God in training. Playful yet ruthless. Foolish yet fierce. Contrarian yet cunning. Seductive yet demur. Enigmatic yet chaotic. Flying-by-the-seat-of-his-pants yet free. The personified trickster is an anti-hero par excellence, a hero bound by neither code nor conduct, a hero with nothing to lose. Nonchalant, unruly, passionate, a dauntless maverick testing all boundaries and stretching all comfort zones, despite resistance from the petty, the prudish, the pacifists, from cowards and fence-sitters. Indeed. Despite even his/her own resistance. For the trickster must first trick himself into thinking he has nothing to lose.

Trickster as Catalyst:

“Freedom is never voluntarily given by the oppressor; it must be demanded by the oppressed.” – Martin Luther King Jr.

The task of a trickster hero is both Dionysian (passionate, artistic, ecstatic) and Sisyphean (unavailing, dauntless, and endless).

It takes a unique type of courage to be a catalyzing agent. Trickster as catalyst is a planter of unwanted seeds, a purveyor of difficult truths, and an agent of brutal motivation. These are seeds that promise to outgrow the stagnant culture of antiquated laws and outdated beliefs. These are the difficult truths that bypass convention and place a mirror in front of the fallibility of the human condition. The kind of brutal motivation that kicks us in the ass for being lazy, shoves us into the abyss for being pretend-forgiving, and drags us kicking and screaming into either the self-improvement or self-destruction of our own unique adventure.

Trickster as catalyst is an existential alchemist. He/She bridges gaps from lead to Fool’s Gold, from Fool’s Gold to the Golden Shadow, from the Golden Shadow to the Overman overcoming himself again and again. He creates and destroys God, and then rebirths God in so many forms that no human culture can keep up. He’s made an art of it, just as he has made an art out of self-transcendence, self-annihilation, and rebirth.

The trickster hero would rather be ashes than dust.

A catalyzing trickster agent is a force to be reckoned with—a force of nature first, a human second. He/She turns the tables on entrenched power through shock and awe campaigns, poking holes in inflated egos through mockery and high humor, flipping the script on any “believers” who place all their eggs into a single basket and then cling to that basket for dear life. They melt down pedestals, knock down high horses, and topple thrones, revealing how nobody should ever take themselves too seriously. They are mighty social leveling mechanisms. Nobody is so powerful that they are out of reach from their ruthless irony and unorthodox ire. Not even God.

Trickster as Rebel:

“I rebel; therefore, we exist.” – Albert Camus

Trickster as rebel is the laughter in the whirlwind. He/She is the jest in the apocalypse. He neither cries nor quibbles at the fact that he is the punchline of an absurd cosmic joke. Rather than tremble, tremble, tremble; he laughs, laughs, laughs. Rather than fear the perceived power of authority, he gets power over power through high humor. The kind of humor that somersaults over itself, gaining momentum, picking up jest and ashes, smiles and razors, thorns and laughter. It’s a cutting humor, an unorthodox humor that takes both thesis and antithesis and smashes it into synthesis, shattering all perceived power constructs and paradigms.

Trickster as rebel embraces the absurdity of existence and rolls with it, juxtaposing juxtaposition, moving into flow states so effortlessly he is overflowing, full of so much jouissance and insouciance that he cannot be contained. Neither by lovers nor jailers. Neither by himself nor God. He is full-frontal dissidence. Too busy transforming demons into diamonds and wounds into wisdom to pay base courtesy or obsequiousness to any perceived authority, whether arbitrary or legitimate.

Contumacious to a fault, trickster as rebel aims to lay faultiness into all default power constructs. Earthquake and upheaval is just his game. Turn everything upside down and let the chips fall where they may. For nothing is worse than power corrupting, except power corrupting absolutely. Preventing this from happening is the trickster hero’s raison daitre. He breaks all compasses so that nobody gets so stuck on True North that they forsake west, east, south, or even more imaginary directions. Better to start from scratch filled with the knowledge of what not to do than to continue with either sickness or stuckness no matter how comfortable.

Trickster as Genius:

“He who makes a beast of himself gets rid of the pain of being a man.” – Dr. Johnson

Trickster as genius has a transcendent capacity for taking on trouble. Remember: he is not a trickster by nature, but by necessity. His/her trickster powers have been built from the quicksand on up to the summit of a house of cards so precarious that it’s perfectly imperfect. Here, summit and abyss are united. Here, the art of having nothing to lose merges with the art of losing everything to nothing. For as Anaxaguras said, “The seed of everything is in everything else.” This is the hard and tough lesson, both for those who take themselves too seriously and for those who are hoodwinked by a profoundly sick society: change your unhealthy ways or be dragged, kicking and screaming, into a healthier way.

But it is nearly impossible to expect a moral awakening from humanity. To achieve a moral awakening requires a force outside of humanity. That force is precisely the trickster hero. It’s the madcap maverick who decides to stare into the infinite masks of himself and dares to come back wearing the mask which breaks all masks and destroys all delusions: the all-laughing, all-mocking trickster mask.

There is no courage more courageous than the courage of someone who has nothing to lose. He has already been destroyed by the abyss and reborn into resilience. He has already been annihilated by a Dark Night of The Soul and reborn into robustness. He has already been torn apart by the absurdity of existence and the infinite nothingness of the existential black hole and put back together again by the sutures of antifragility. No authority outflanks him. No God beleaguers him. It’s all a cosmic joke at best and a delusion at worst. So be it.

The trickster hero is here to put the cartoon-in-the-brain of it all on blast. He/she is here to tip the scales in favor of laughter over seriousness, humor over power, and adventure over comfort. Most of all, he is here to force playfulness and lightheartedness down the throats of all prudes, goody-two-shoes, tyrants, psychopaths, cowards, and milquetoasts. Screw them all if they can’t stare into the cave they fear, the abyss they dread, or the God they bow down to and have a laugh at their own free-falling delusions of grandeur.

Image source:

Away by Julian Majin

About the Author:

Gary Z McGee, a former Navy Intelligence Specialist turned philosopher, is the author of Birthday Suit of God and The Looking Glass Man. His works are inspired by the great philosophers of the ages and his wide-awake view of the modern world.

This article (The Art of Having Nothing to Lose) was originally created and published by The Mind Unleashed and is re-printed here under a Creative Commons license with attribution to Gary Z McGee and themindunleashed.com. It may be re-posted freely with proper attribution, author bio, and this statement of copyright.