Conversatio Divina

In Order to Grow, We Must Transgress

Michael Simmons

“In its enthusiasm for the divine light, Christian theology has not always done justice to the divine darkness […] Then we try to live up to the standards of a God that is purely light and we can’t handle the darkness within us. And because we can’t handle it, we suppress it.”Connie Zweig, Meeting the Shadow (Penguin, 2020). 132.

– David Steindl-Rast

01.  Introduction

“I ask for a new God.” This was the response from a little boy one Advent Sunday morning at his church’s “children’s time.” The children’s pastor had asked the group of 2-5 year olds what they wanted for Christmas, to which this little one responded, “I ask for a new God.” “A new God? Wow! I’ve never ever heard that before.” The children’s pastor exclaimed as the congregation anxiously laughed. The pastor turned to the next child, “What would you like to ask for? The options are endless.” In seeming solidarity with the little boy, she responded, “I ask for a new God.” The anxious surface tension breaks as the adult onlookers embrace the moment. A third child approaches, to which the pastor asks, “Um uh, are you also going to ask for a new God? The little girl pauses and responds “A better Jesus.” The pastor jokingly confesses to utter failure, as the entire congregation erupts in laughter. 

In this moment, the congregation connected with the divine darkness. Perhaps in their enthusiasm, or likely lack thereof, for the divine light, these three children illuminated the divine darkness. They unexpectedly brought to speech something suppressed, unnamable, and entirely transgressive. Yet, exposing that shadow left the whole community more whole and connected to one another than before.

What is shadow? The term shadow was developed by Swiss psychologist, Carl Gustav Jung to denote the parts of ourselves we hide, repress, and deny. Our shadow is neither good nor bad–we must understand this first and foremost. The shadow is more like a “long bag we drag behind us” that contains the parts of our humanity we fail to see, know, or experience.Robert Bly, A Little Book on the Human Shadow (Harper Collins, 2009). Our shadow is formed significantly in our earliest years, and our primary caretakers, teachers, friends, church leaders, and our broader culture all play a role in telling us who, and how, we should and should not be.

02.  How is shadow formed?

Jung held that the ego, Latin for “I,” was the conscious part of our personality, and the center of who we know and understand ourselves to be. If I say, “I am a writer,” I am making a statement of who I know myself to be, and how I identify in the world. The ego’s primary function is survival, and its mission is to help us meet our basic needs for food, shelter, clothing, love, social acceptance and advancement. Anything that doesn’t help us meet these needs, especially early in life, falls into our shadow, so our ego is also primarily responsible for shadow formation. The ego is like a quality assurance manager, which displays our most acceptable parts, and discards our unacceptable parts.

To a degree, shadow formation is developmentally necessary early in life as we assimilate to our cultural and societal context. However, as we move into adulthood we find our previously discarded parts to be necessary for a fulfilling and whole life. Take the emotion of anger as an example. If anger was suppressed in your home and broader culture, you likely internalized that suppression in order to find acceptance and meet your basic needs. But as an adult, you may experience difficulty setting boundaries, or say “no,” leaving you feeling drained, emotionally vacant, and chronically resentful. Anger is our boundary-setting emotion, and when our anger is shadowed we tend to either lack agency to set healthy boundaries, or because we feel so overrun, we wall people out with whom we truly desire connection.

Many people I work with understand anger as inherently bad, or at least it is an emotion to which they have little to no access. Those raised in more religious environments often equate anger directly with sin, which causes an existential anxiety around their standing with God. To find safety, they strain to shove it back down into the long bag.

Such an adversarial relationship with anger serves them well for many years, and they’re often praised for the agreeability, and “can do” attitude. However, this posture takes a toll eventually–in exchange for their obedience to the ego-expectation of agreeability, they violate their own needs. Rather than healthily expressing their anger, it becomes lodged in their body, mind, soul, and deteriorates their relationships through resentment and passive aggression.

03.  What is shadow work?

So, what is shadow work, and how does it help? Simply put, shadow work is any transgressive act or process of slowly opening the “long bag,” welcoming, integrating, and companioning the portions of our humanity we previously hid in order to meet the expectations of our parents, caretakers, peers, and larger social environments. The word transgression comes from the Latin meaning to go or step across. Shadow work is inherently action oriented, and requires us to step across or go beyond the ego-constructs to interact with, and learn from what we encounter in our shadow. Like a pail enables one to draw water from a deep well, shadow work provides a container to lift our hidden humanity to the surface of consciousness and into the Divine Light. It is the everyday spiritual practice of “stepping across,” of going beyond the preconceived boundaries of ego-narratives, and into the murky, wild shadow-lands of the forgotten self.

04.  The Transgressiveness of Christ

“Some people came and asked Jesus, “How is it that John’s disciples and the Pharisees’ disciples are fasting, but yours are not?” Jesus answered, “[…] no one pours new wine into old wineskins. Otherwise, the wine will burst the skins, and both the wine and the wineskins will be ruined. No, they pour new wine into new wineskins.”Mark 2:21-22. NIV.

– Mark 2:21-22 NIV


Early in Mark’s gospel, Jesus offers this metaphor of new wine in new wineskins, just after he commits a number of transgressive acts: healing and forgiving a man’s sins, interacting with a tax collector, eating with sinners, choosing to not fast, and teaching his followers to do the same. We’re often taught to think of Jesus as the image of obedience, but here we see him as an image of transgressiveness.

Shadow work invites us to lean into and embody the transgressiveness of Christ. The metaphor of the new wine and wineskins reminds us that the old containers, which cultivated life in us at one point, may be insufficient to hold the life springing up within us today. The transgressiveness of Christ is not simply about breaking our old containers, but about allowing our life to flow, and trusting that something more expansive will hold the new and unformed movement. As I write in a previous post, If I have learned anything from Christ, it is that transgression of the “law” is often simultaneously an act of fidelity to oneself, to the Divine, and to the real needs of others.

05.  Transgressing through Imaginative Prayer

“Indeed, if we strive to be too good we only engender the opposite reaction in the unconscious. If we try to live too much in the light, a corresponding amount of darkness accumulates within.”John A. Sanford, Evil: The Shadow Side of Reality (Crossroad, 1981). 23.

– John A. Sanford


Saint Ignatius of Loyola, a 16th century Spanish Catholic priest, is credited with originating the spiritual practice of imaginative prayer. This practice contemplatively guides participants into greater connection and wholeness by imaginatively engaging biblical stories and events, as well as personal spiritual experiences. About 3 centuries later, Carl Jung developed the concept and therapeutic tool of active imagination as a way for his patients to engage the symbols, images, and experiences they encountered in their dreams.Note about active imagination.

Technique aside, these practices offer access to what is hidden in our shadow because they engage our imagination, which is not dominated and controlled by ego awareness/consciousness. Our imagination is autonomous from the ego’s initiative for survival, so it is free to transgress the perceived and prescribed limitations of our ego, our family of origin scripts, and the broader cultural and religious expectations (this is why Jungian psychologists put so much emphasis on dreams and dream work). Imaginative practices allow us to transgress the “lawful” threshold of our shadow, so we can welcome, integrate, and companion what we find.

06.  Discovering who we are not

“Look for your other half who walks along beside you, and tends to be who you are not.” 

– Antonio Machado


The gospels are full of images depicting “who we are not.” Perhaps it is the infamous tax collector, the prostitute, the Pharisee, or the demon possessed man. We’ve all likely engaged these characters through some sort of contemplative or imaginative exercise. The Zacchaeus story is a classic shadow work story where the shadow figure emerges, and is imaginatively welcomed through compassion, hospitality, and forgiveness. But what if we shifted our gaze from the compassion of Christ to the transgressiveness of Christ? How does this change our engagement with this story? What possibilities open for shadow work when we see Christ as one who steps across and violates our ego narratives and our images of purity and obedience?

These questions may feel transgressive to even pose, but is it possible that our image of Jesus needs to shift in order to breach the threshold of the long bag we drag behind us? To continue with Jesus’ metaphor of the wineskins, is it possible our image of God has been stretched out to the extent that it can no longer contain the life springing up within? Perhaps the fermentation process your life is undergoing requires you to transgress the old ways, and allow yourself to be poured into unfamiliar containers that do not fit the script, and violate the lawful ego-centric spirituality.

07.  Transgressive Spirituality

As a shadow work facilitator, I meet people often for whom the old wineskins of their faith no longer serve life’s fermentation process. They try to pour their lives into the old containers, but the containers simply cannot adequately support the life rising up within. This is usually because the old containers require us to live up to an image of God that is one-sided, fully illuminated, and ultimately aligned with the ego-narratives that helped cultivate our shadow in the first place. This “new wineskin” process is popularly referred to as deconstruction, and what is being deconstructed are the egoic expectations that served a vital purpose at one point, but are no longer structurally sound. Transgressive spirituality allows us to enter into the stories and symbolism of the bible through a new way by violating our ego-expectations of who Christ is, so we can discover who we are not.

08.  A Note to Spiritual Directors and Soul Companions

As soul companions, our work is to create space for this transgressive process, and welcome the shadow as it appears. Of course, we must be engaged in the same transgressive process ourselves. It is through such attentiveness to the hidden recesses of our soul that both new wine and wineskins emerge. Wine is an ancient symbol for the inner life, of communion with the Divine, of joy, life, and liberation. Receiving our shadow brings about vitality to our relationships because it is necessarily inclusive to the fullness of our humanity, and we can only receive in another that which we’ve received in ourselves.

09.  Apply It

In Mark 2 we find several examples of Jesus transgressing a number of Jewish laws. The following prompts will guide you through this story to illuminate possible invitations to shadow work, and/or awareness of how the Self is already doing this work in you.

  • Read Mark 2 in its entirety
  • List the scenes where you read Jesus transgressing a law, expectation, common practice, etc.
  • Which scene holds the most energy for you, or feels the weightiest? Notice your leanings toward or away from a particular scene. Check in with your body to see how it reacts to each scene.
  • Once you’ve picked a scene, imaginatively enter into it. What do you see? What do you smell? What do you feel in your body? What message are you’re telling yourself about the scene, and the people in it?
  • Where is Jesus in this scene? What is he doing? What are your judgements (positive or negative) about what he’s doing?
  • What questions, curiosities, fears, or longings do you have that you want to bring to Jesus? Feel free to write those down in a journal.
  • Sit with what surfaces for you. Wait for a response? What images, words, phrases, or actions surface as you engage Jesus?
  • Now, write about what you discovered, or new awareness that surfaced during this imaginative exercise.

10.  Bibliography

Bly, Robert. A Little Book on the Human Shadow. Harper Collins, 2009.

Chevalier, Jean, and Alain Gheerbrant. The Penguin Dictionary of Symbols. Penguin Publishing Group, 1996.

Sanford, John A. Evil: The Shadow Side of Reality. Crossroad, 1981.

Zweig, Connie. Meeting the Shadow. Penguin, 2020.


About Michael Simmons

Michael is a spiritual director, shadow work facilitator, and writer. He is ordained in the Free Methodist Church, and holds a Doctor of Leadership from Portland Seminary. He is also a board member of The Companioning Center, and Deep Water Men’s Ministry, both based in Newberg, Oregon where Michael lives with his partner, Liz, and their two kids, Bina and David.

Michael’s Companioning Our Shadow Course runs July 26 – August 23, 2023 | Wednesdays, 9am-11am PST

To connect with Michael for spiritual direction or shadow work, visit, or email him  at  Keep up to date with opportunities, and Michael’s latest work here.