top of page

The Journey: The Ordeal

facing the dragon

My Dear One,

When my oldest son was a toddler, he attended a preschool at a church named St. George’s. In April each year, they celebrate St. George’s Day by reenacting the most famous story about him, the slaying of the dragon. It is said that St. George once came to a town that was terrorized by a dragon who demanded the life of one young maiden each day or else he would lay the entire population to waste. On this particular day, the king’s daughter herself was chosen by lottery. Upon learning of her tragic fate, St. George offered to slay the dragon instead and, noticing a weakness under its arm where it had no scales to protect it, he thrust his sword, slaying the beast. And so out on the playground, after many days of painting cardboard boxes green, stacking them together into a giant mound to create their “dragon,” a mob of children dressed as knights charged out the door with cardboard shields and swords in hand to decimate the beast of their own creation.

This is the story of this week in total.

On our Transformative Journey towards the Sacred Center, there will always be a greatest gatekeeper whom we must face before the final test. This gatekeeper will usually take the form of “a dragon,” an unimaginably large and terrifying beast who resides within the innermost cave who has the power to slay us in one fiery breath. What terrifies us most about this beast is that it cannot be escaped because, ultimately, it is not some external force but rather belongs to us, within us, as the dark Shadow of all we would rather not face within ourselves. This beast, the dragon, lurks in the darkness, frightening us away, lying in wait should we dare approach it. It guards the innermost treasure, the source of our ultimate liberation and redemption should we be able to grasp it. But only by overcoming the dragon can we attain it’s bounteous treasures.

Having gathered up the courage for The Approach, we now must find the courage to come face to face with the issue itself.

Movie Example: The Hobbit’s Smaug

Earlier in this series, we looked at the scene in J.R.R. Tolkien’s The Hobbit when Gandalf the wizard invited Bilbo the hobbit to go with him on an adventure. It turns out, this adventure was to recapture an immense treasures that rightly belonged to another people, the dwarves, taken 150 years prior by the great dragon Smaug. Bilbo’s job, as unlikely as it might seem for a timid little hobbit, is to sneak into the cave where lies both the treasure and the great dragon, Smaug, and search for the dragon’s weakness. While inside the cave, Biblo comes face to face with the dragon and finds the place near its heart where a scale had once been damaged. This piece of information would prove crucial when the dragon emerges from the cave and another character, an archer, is able to kill the dragon with an arrow to the vulnerable spot.

You can enjoy the entire encounter between Bilbo and Smaug in Peter Jackson’s movie trilogy here

Biblical Example: Garden of Gethsemane

Jesus’ approach to the cave was his approach to Jerusalem, the place where he knew his life would find its end. After preaching in the temple, turning over the money-changers’ tables, and eating a last supper at Passover with his disciples where he foretells his betrayal by one of them, Jesus goes to pray in the Garden of Gethsemane. It is there he asks God, if there be any way, to “let this cup pass” from him, but if there is not he pledges to accept it. In the dark of night, Jesus has entered into the cave of his own mortality, facing this reality with resolve. Guards arrive to arrest him at which one of his disciples, Peter, pulls out a sword and cuts off the ear of one of the arresting party. Peter here serves as the great knight of this scene, willing to go to battle with the dragon in order to protect the innocent. But, in a dramatic reversal, Jesus tells Peter to put away his sword.

Then Simon Peter, who had a sword, drew it, struck the high priest’s slave, and cut off his right ear. The slave’s name was Malchus. Jesus said to Peter, “Put your sword back into its sheath. Am I not to drink the cup that the Father has given me?” John 18:10-11

And in Luke’s telling of the story, Jesus even heals the injured man:

When those who were around him saw what was coming, they asked, “Lord, should we strike with the sword?” Then one of them struck the slave of the high priest and cut off his right ear. But Jesus said, “No more of this!” And he touched his ear and healed him. Luke 22:49-51

Rather than drawing the sword to slay, Jesus demands the sword be withdrawn and he reaches out to heal. Herein lies the great difference between Jesus and the heroes of most other tales. Other heroes find victory through inflicting violence and defeat upon an enemy. Jesus’ victory will come through offering peace and forgiveness to his enemies even as they inflict violence upon him.

It is telling that from St. George to The Hobbit we still prefer stories where the dragon gets killed rather than befriended, where the enemy is extinguished rather than the hero. Noticing and embracing this distinct difference is key to our own transformation.

Your Ordeal

In The Hero With a Thousand Faces, Joseph Campbell writes of this stage in the journey, “In the vocabulary of the mystics this is the second stage of the Way, that of the ‘purification of the self,’ when the sense are ‘cleansed and humbled,’ and the energies and interests ‘concentrated upon transcendental things’; or in a vocabulary of more modern turn: this is the process of dissolving, transcending, or transmuting the infantile images of our personal past.” (THWATF p. 84.) Campbell goes on to spend a few chapters on different manifestations of “The Ordeal” rooted in mythology.

This sums up the work that is before us, as our dragon was almost always birthed within our formative infant, child or adolescent stages. It comes to maturity and may first be recognized later some stage of adulthood, but its tale reaches all the way back to some fear planted within the dark caverns of insecurity hollowed out in the recess of our psyche as we enter into the early stages of self-awareness. Our dragon may well take on the skin of outside forces later on but its genesis is almost always internal rather than external. The bully preys upon our existing feelings of inferiority. The rejection by a love interest preys upon our existing feelings of being unloveable. The early career missteps prey upon our existing feelings of being a fraud. The need to “become someone” preys upon our existing feelings of being unoriginal. The drive to help someone preys upon our existing feelings of being unappreciated. The list goes on.

Knowing your Shadow side, the dark underbelly of your personal identity, is crucial when it comes to the work of facing The Ordeal. To face your dragon well it helps to know its name … and also where it lives, what it knows, what it thinks it knows but doesn’t, what time it likes to take a nap, what its favorite kind of pizza is, …

There are different ways to do the work of getting to know your dragon and see your Shadow and you likely have experienced several: psychotherapy, spiritual direction, Myers/Briggs typology, Keirsey temperament sorter, Ignatian Spiritual Exercises, each has their own unique gifts, but none has brought me face to face with my Shadow quite so clearly as the Enneagram. In the Enneagram it was placed so squarely in front of me that I couldn’t avoid facing it any longer, I practically fell into the innermost cave ready or not.

Confronting my dragon/Shadow however did not destroy me but instead healed me, or rather continues to heal me, as I see my unhealthy patterns for what they are. Rather than destroy that part of me I dislike most, I have come to a greater acceptance of that part of me, I’ve gotten to know it, and in doing so it lost it’s only real power over me … to make me afraid as any good dragon will.

Your Journey this week

What shape is your dragon taking these days? What is its name, where does it reside, what awakens it and prompts its fury? What is guarding the gateway to greater freedom and the future you initially felt called towards several weeks ago? Here is your chance to face it and call it by name.

If you know your Enneagram number, this week I encourage you to go back and read about it again, looking for the ways your strengths and weaknesses are manifesting in your story right now. You can find a basic overview of the nine types here And if you have never worked with the Enneagram or taken the time to discover your number, I highly recommend you spend the few dollars it takes to get the best test out there, the RHETI at

Once you’ve found your number or refreshed yourself about it, sit down and take some time to really detail the form of your dragon these days. How is it trying to keep you at bay? What is it that it is guarding so jealously? What is its weakness? Do you feel inclined to exploit that weakness or work to love and heal it instead?

If your instinct has long been to defeat or repress your dragon/Shadow, might I suggest you instead try the approach of Christ, to reach out, seek to have mercy and heal it, acknowledging the initial wound which gave birth to it in the first place, and using the power of love rather than violence to deal with its presence in your life?

“Returning hate for hate multiplies hate, adding deeper darkness to a night already devoid of stars. Darkness cannot drive out darkness; only light can do that. Hate cannot drive out hate; only love can do that. Hate multiplies hate, violence multiplies violence, and toughness multiplies toughness in a descending spiral of destruction.”

from Strength to Love by Martin Luther King, Jr.

following The Way,



bottom of page