To Grow We Must Transgress

Oct 31 / Michael Simmons
“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.” [1]
Mark 2:21-22 NIV

As a shadow work facilitator, I’m often asked, what is shadow work? By more skeptical inquirers, there is usually a level of suspicion, fear, and even repulsion at the term “shadow”. Perhaps this is for good reason. Shadow work requires first, one to acknowledge they have a shadow, or hidden self, and second, a willingness to engage in dialog with their shadow side. 

“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.” [2]
                                                                                                                                                                              David Steindl-Rast

The term shadow was developed by Swiss psychologist, Carl Gustav Jung to refer to the parts of ourselves we hide, repress, and deny. Our shadow is neither good nor bad. It is more like a “long bag we drag behind us” that contains all the parts of our humanity that we fail to see or know about ourselves. Our shadow is formed significantly in our earliest years, and our primary caretakers, teachers, friends, church leaders, and our broader culture all play roles in cultivating it. 

"Look for your other half who walks along beside you, and tends to be who you are not." 
                                                                                                                                                                             Antonio Machado

So, what is shadow work? Simply put, shadow work is a transgressive process of opening the “long bag,” welcoming, and choosing to learn from our hidden self. The word transgression comes from the Latin meaning to go or step across. Shadow work invites us to create new containers to hold the ancient life bubbling up from those parts of ourselves we’ve hidden, rejected, and denied.

Early in Mark’s gospel, Jesus offers a metaphor of new wine in new wineskins, just after he commits a number of transgressive acts: forgiving a man’s sins, interacting with a tax collector, eating with sinners, and choosing to not fast, while teaching his followers to do the same.

We’re often taught to think of Jesus as the image of obedience, but here we see an image of transgressiveness. Shadow work requires that we 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 no longer be functional. 

The transgressiveness of Christ is not simply about breaking our old containers, but about allowing our life to live us, and trusting that something more expansive will hold us. If I have learned anything from Christ, it is that the transgression of the law is often simultaneously an act of fidelity to oneself and to the Divine. 

“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

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. [4] 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. 

Apply It
Jung believed that our shadow did not simply lie dormant, but showed up in our relational interactions in the form of projections. We often know we are dealing with a shadow projection when we experience a heightened energy surge (positive or negative) around a particular person or people.

Who is someone you currently cannot stand, who repulses you, and you aim to avoid? Or maybe there’s someone you admire, envy, and assume their life to be ideal. Perhaps you have legitimate reasons for how you feel toward them but allow them to serve as a mirror to see what may be lurking in your shadow. 

I invite you to explore this further with me by attending both courses I offer through the Companioning Center. The first experiential course is a 2 hours robust introduction to shadow work by way of welcoming our emotions. The experiential is a prerequisite for the second course. The second course is a 4 week in depth journey into concepts, tools, and practices for this work. Join me by signing up below!

Prerequisite Experiential:
Companion Our Shadow: Welcoming Emotions 
Companion Our Shadow: Welcoming Emotions (Self-paced) 

Formation Course:
Companion Our Shadow: Befriending Emotions, Healing Relationships

[1] Mark 2:21-22. NIV.
[2] Connie Zweig, Meeting the Shadow (Penguin, 2020). 132.
[3] John A. Sanford, Evil: The Shadow Side of Reality (Crossroad, 1981). 23.
[4] Jean Chevalier and Alain Gheerbrant, The Penguin Dictionary of Symbols (Penguin Publishing Group, 1996).

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.
Mark 2:21-22. NIV.
Zweig, Connie. Meeting the Shadow. Penguin, 2020.

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. If you’d like to connect with Michael for spiritual direction or shadow work, visit, or email him at You can also check out his column, Transgressive Spirituality: Life Through the Lens of Jungian Psychology. Be sure to check out his latest work and upcoming courses here.