It’s Time to Meet Your Shadow Side

Monday, November 13, 2017 - 5:15 pm

It’s Time to Meet Your Shadow Side

A couple years ago I was in Telluride, waiting around for a talk to begin at the Nugget Theater downtown. I was talking to Lucy, the woman who has owned the 186-seat theater for the last 20 years. In thinking about that small mountain town rich with mining history, I sensed that those walls had seen more characters than just those featured in the infamous film festival movies. I asked her if the place was haunted. “No,” she replied with a smile. “But the staff shirts do say ‘behind you in the dark.’

This came to mind as I was thinking about shadow and leadership. The shadow is often referred to as a black bag that you drag behind yourself, filled with all the things that you haven’t been able to consciously look at for a variety of reasons: You weren’t ready to, you couldn’t, it was too much, etc. And yet, wherever you go, there it is: behind you in the dark.

Ah, shadow.

Years ago before I began a deep dive with my first coach and mentor, she asked me:

“Are you willing to look at the shadow-side of you? The part of you that doesn’t want you to do all that you aspire to do? Are you willing to see, listen to and look directly at anything in you that is wanting to hold you back? And, what might be the greatest potential gift in doing that?”

I had little idea what this meant. The thought of looking at something I hadn’t even known about seemed terrifying, quite honestly. Thinking about it felt like this image from Tim Burton’s sketches.

An illustration from Tim Burton's 1982 film "Vincent."

An illustration from Tim Burton’s 1982 film “Vincent.”

At that point, my mind raced a bit: Why hadn’t I seen this shadow thing before? What was I going to find? Looking at this seemingly terrifying, potent dark thing was going to be a gift? What the… ?!

She explained that shadow was that part of us that said: “It’s better to be small and inauthentic than emotionally crushed.” It’s the part of us that wants to keep us safe. The greatest potential gift of looking at that square in the face still seemed to me a bit like eating an entire box of Cracker Jacks only to be left with a gut ache and a lame-ass prize. But I trusted her, and my nighttime vision, and therein began the exploration of the dark.

The dark side wasn’t as terrifying as part of me had imagined. I met and got re-acquainted with stuff from childhood — happenings that my little self tried to make sense of and those young reasonings that were still running in the background cycles of my experience, which created a current sense of reality for myself that was operating from an old map. And that old map was projecting old things that were not going to get me where I aspired to be, and in fact were getting in the way.

“Shadow Work is consciousness-seeking,” writes David Kantor in his book My Lover, Myself:

“It is a descent into the underworld in search of  the dark side of the soul for the purpose of bringing our shadows back up into the light of day where we may come to know them and reconnect with them. Our shadows are a projection of reality rather than reality itself. The problem with our shadows is not that we have them, but that we deny their presence. When we continue to suppress our shadows, they overwhelm our sense of reality so that we come to believe that their voices are the ultimate truth. […] Once we become aware of our shadows we start to understand how subjective our view of reality really is.”

This is the importance of shadow work: If we don’t work on our stuff, our stuff will work on us. It will work on us while even our best intentions are to have an amazing life. And it will show up everywhere projecting its own reality in front of us like a bad movie — or perhaps recurring situations you keep finding yourself in — until it is brought to light. Once we see it — and learn how it operates — we can recognize it when it shows up.

Reclaiming what’s in shadow brings those pieces of you back into wholeness. It allows you to see the projection and walk out of that theater into your more dimensional life. It allows you to harness your potential more effectively. Embracing what’s shadowed helps you find a tender love for yourself, warts and all.

I found more clarity, like I was shifting from a fragmented camera obscura projection of reality to the direct experience in the dimensions of embodied life. More of my resources showed up for myself, my work, my relationships, my play since the old maps of distorted images stopped running as background cycles. With that energy freed up, I found a refreshing and renewed sense of life itself.

“How you choose to interact with the opposing forces within you will determine your life. Starve one or the other or guide them both,” recounts an old Cherokee story. Learning to work with shadow could be one of the most liberating things you can choose to be conscious about, in your relationships with yourself, your work, intimate relationships, and living more fully in alignment with your purpose.

Know what the beautiful part is? When it comes to shadow work, your medicine is always right in front of you: What you’re creating is telling you something potent about how your shadow side may be showing up for you. It’s good to get curious, look awry, and wonder what’s playing on the screen from behind you in the dark.

This interview with Parker Palmer, I hope, shines more light on the shadow side — specifically how it shows up in leadership and why it’s an important piece of self-inquiry for anyone who works with humans.

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Ali Schultz

is co-founder and COO of As a coach, her superpowers include getting her clients to tap into their innermost being where the wellspring of their creativity resides. She draws on her 11 years in business where she honed her operational skills managing projects, teams, and human resources at startups and developing brand strategies. Before Reboot, she worked with Jerry Colonna in the first incarnations of the life-changing CEO Bootcamps. She has a master’s degree in religious studies from CU Boulder, has studied transformational NLP at NLP Marin, and is completing certification at EQUUS Experience in Santa Fe, NM. Ali is also an artist and an avid horsewoman. Art and horses are perhaps her favorite coaching modalities. You can read her infamous newsletters at the Reboot Blog.

Share Your Reflection


  • Nancy W.

    This article seems incomplete to me without the mention of psychiatrist C.G. Jung of Switzerland and his theory of analytical psychology given his work and theory are clearly present in the text of the article.

    “The shadow is a moral problem that challenges the whole ego-personality, for no one can become conscious of the showdown without considerable moral effort. To become conscious of it involves recognizing the dark aspects of the personality as present and real. This act is the essential condition for any kind of self-knowledge, and it therefore, as a rule, meets with considerable resistance. Indeed, self-knowledge as a psychotherapeutic measure frequently requires much painstaking work extending over a long period of time.” (C.G. Jung, Collected Works Vol. 9ii, par. 14)

    “One realizes, first of all, that one cannot project one’s shadow on to others, and next that there is no advantage in insisting on their guilt, as it is so much more important to know and possess one’s own, because it is part of one’s own self and a necessary factor without which nothing in this sublunary world can be realized.” (C.G. Jung, Collected Works Vol. 14, par. 203)

    “This process of coming to terms with the Other in us is well worth while, because in this way we get to know aspects of our nature which we would not allow anybody to show us and which we ourselves would never have admitted.” (C.G. Jung, Collected Works Vol. 14, par. 706)

  • Peggy

    I am always touched by the ways you express the inexpressible Ali. This time, the power of the shadow “…which created a current sense of reality for myself that was operating from an old map.” I am in another cycle of this discovery. Always more to be revealed in this deepening with ourselves! Thank you for the timely reassurance!

  • Genevieve O’Reilly

    The illustration reminds me of a saying my father used..”the devil dancing on your pillow”. It has become a powerful metaphor in our family for our collective madness. As soon as we use it we know that it means those times in the wee hours when the ‘shadows’ come out to seek retribution.

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