Shadow Work: 14 Day Challenge

I have seen a lot of people ask questions about shadow work, so I wanted to talk about what it is and a method that really worked for me. I have dabbled with working with my shadow for many years at various workshops and in therapy, but it was not until I was having a deep crisis of self, did I really go deeper. I am going to be vulnerable about myself in ways I normally would have found difficult, but I hope by showing what I did and the places I went inside myself, that I can help others.

As one of my mentors said, our shadow is “all the things that we hide, repress, or deny”. Our shadows are the parts of ourselves that we have divorced from ourselves due to trauma, guilt, shame, or any other negative emotion that we could not process. For example, if a child is caught eating a cookie and their parent shames them then they might hide eating cookies in general. Then this could turn into sneaking around snacks since an otherwise health instinct of feeding yourself into a bad habit.

For me, my childhood abuse, neglect, and abandonment led to trying to fill those wounds with sex addiction, egotism, and a host of other things that I am finally in recovery from. The tool that helped me the most was a 14 day shadow challenge I found online. Below is the challenge that I did. It was originally found at:

Below is my journal entries for each of the challenges.

Shadow Work Challenge Day #1:
Artistic Expression- “How Do You See Yourself?”
Using an artistic medium to create a visual representation of how you see yourself.

This was very challenging for me. Visual arts are my weakest thing, but I like doing collage. I used photo editing software to make a visual collage.

The core picture is from when I was dj-ing and hosting a local goth club night with a friend of mine. It represents the persona/mask I have tried to show to people as someone who is charismatic, fun, and “mysterious”. It is very much the mask of my egotism. The peacock feathers also represent this egotism and my tendency to want to show off to be liked. The picture of a smiling me in the left eye is my authentic self trying to creep out, but also the part of me that seeks the approval of others and wants to be liked. The occult “eye” symbolizes how I like to communicate and express myself through spiritual metaphors and occult knowledge (which is a double edged sword since I want people to like me for what I know and it is honestly the thing that gives me the most personal joy and fulfillment other than writing). The monkey represents my tendency towards addiction and escapism that claws on me and I keep in check. The black hole at my chest represents my wounded heart that I try in vain to feed with external sources when I cannot love myself. The baby imprisoned in the chest (an actual baby picture of me) represents my inner child imprisoned by my ego that is in need of love and nurturing. Lastly, the dark circles represent emotions of guilt and shame that I try to avoid, but nevertheless haunt me.

Shadow Work Challenge Day #2:
Introspection- “What Don’t You Like about Yourself?”
Identify things about yourself that you don’t like or feel insecure about.

I have a few things I don’t like about myself, I think I can sum it up under one major thing: Cowardice.

I cower at honesty. I am good about lying to myself about how things are better than they really have. I can have a “positivity bias”. I tend to look at the bright side of something and the future, instead of focusing on pain in the past. If I don’t look at the past honestly and see the pain that was inflicted upon me, or that I have inflicted on others- healing cannot occur. A lot of bad things happened to me as a kid, and I often try to gloss over them instead of acknowledging them. I also have done bad things to others that I am deeply ashamed of. This is the psychic equivalent to sweeping a landmine under the rug- one that my loved ones and I have unfortunately stepped on more than once. I am a coward when it comes to the truth because it forces me to face truths that are painful to bear in my mind and hold in my heart. If I am honest, it is difficult for me to be honest when I have done something wrong and it takes me longer than others to own up to things (for example, out of anger I insulted two people close to our family and it took months for me to write out sincere apology letters).

I cower behind procrastination. I waste time and lose focus, when there is so much I want to accomplish. I will waste time doing mindless and fruitless things, then complain about how little time I have to get things done. While I can switch focus on things, I am far more effective when I can devote time to something wholeheartedly and get into a groove.

I think another source of my cowardice is my insecurities about my intelligence, physical appearance, race, and gender (no big deal). I went to a really good school and although I was smart, I felt my friends were smarter than me and I felt bad about my ability to perform academically and intellectually. Also, it didn’t help that I was always researching stuff on my own and talking about things my friends or family didn’t find interesting. I am insecure about being bi-racial. Not as much as I used to be, but sometimes I still find shutting down the voice in the back of my head that worries about being to black to white people, and too white for black people (I still remember about being called an “oreo” for years in elementary school). I feel that I do not look good enough, but some of that relates to my racial features and weight, and that stems more from childhood trauma than what I currently feel.

It is interesting to see how many of my insecurities actually come from trauma in formative years and come from feeling rejected by others or perceiving myself as less than someone else.

Shadow Work Challenge Day #3:
Artistic Expression- “How Do You See the World?”
Using an artistic medium to create a visual representation of how you perceive the world around you.

I see the world fundamentally split. Emotionally- I feel that the world doesn’t have enough mercy or compassion. I feel that we are all blind to what other people are going through and there is not enough compassion. I see the greed and corruption in this world and sickens me. I think we are all sick of it and it infects the world like a virus. I fear that all of our combined shadows will consume the world and that the doomsayers that have not worked to make themselves and the world around them better will win. I also try to cultivate “agape”- that sense of altruistic love that is selfless and rooted in the spiritual truth that we are all connected and that as the Unitarian Universalists say is rooted in the “inherent worth and dignity” of all people. Spiritually, I see the world as a school where the soul learn and evolves. I believe that just as our DNS is a blueprint for who we are- there is “blueprint of the Gods” of the ideal way we can construct the world, and that is the responsibility to be the “carpenters” that build that Divine plan on Earth. “As Above, so Below.”

Shadow Work Challenge Day #4:
Introspection- “What Bothers You About Others”
Identify things about others that get under your skin.

The point of this exercise is to acknowledge that the things I despise the most in others are the things that I myself do and need to work on. There are not a lot of things that get under my skin about people, but there are few. I despise things that most sensible people hate such as racism, chauvinism, etc, but the things below are the ones that cause an immediate, reflexive emotional reaction. I also want to look at these things as they relate to my “wounded child” self since I will be doing some inner child healing later in this shadow work process.

Judgment- I can understand hypocrisy on some level- since we are all works in progress and it is work to have our actions and words match up. What I cannot stand? Is when I am judged for something the person that is judging me does. It will drive me a little insane. On the flip side of this, I sometimes judge people without looking at their circumstance and having perspective. When I find myself judging people, I need to look at why I am doing it and how it speaks to who I am and what I need to process. For example, if I am judging someone’s parenting- I need to ask myself what issues am I having being a parent right now. Part of childhood trauma is that I was often judged for not having things that some kids had, being overweight, or whatever they decided to “other” me with. I feel that part of my programming I created in defense of that was to judge them, and use that judgement as a shield to protect me from and weapon with which to strike back.

Selfishness- I try to be aware of the relationship between the people around me, or connected to, and the resources we have to share. This could be anything from people not being considerate (I am looking at you people that don’t use their turn signal) to taking the last of something I was looking forward to eating in the fridge (don’t take food from a Taurus). Thinking about this, I need to look at the times that I have been selfish. There is a difference between being selfish and loving yourself in a healthy way to get your needs met. While getting my needs met, I must take meneeds into account as well as my impact on others, selfishness is putting my needs over and above others. When I was a kid, I did not get all my needs met (like most of us) and there is a childhood wound I need to address there. Part of my “wounded child” needed to be a little selfish to help get basic needs met. Now that I am an adult, this is programming that no longer serves me.

Interruptions- I try to get a lot done and communicate a lot. One thing that causes me to pause so I can “respond and not react” is being interrupted in conversation. If I am communicating something, it is because I think it is important or I just like to talk about it. Over the last few years, I have to acknowledge a few important things:

My ADHD makes me want to “word vomit” everything I know about a subject, so I need to make sure I respect the time of others (see Selfishness above).
A conversation is not about just sharing information, but connecting and establishing a relationship. I have no right to complain about feeling disconnected to people if I don’t take time to establish a rapport through actual communication, where I make space for someone’s emotions and point of view, and appreciation of the person and what they say.

I like to talk and I want people to like me for being smart and saying cool things. This comes both from the trauma of childhood loneliness and wanting to be accepted by others when I was not as a child by both family and peers.

Shadow Work Challenge Day #5:
Artistic Expression- “How Do You See Your Shadow?”
Using an artistic medium to create a visual representation of your shadow.

This is my shadow. I will call him Squiggly T. Shadow. He has wide eyes with a manic wonder and is always too excited. His heart is caged since he tries to feel love externally and not internally. He is a mess, but he wants to look fancy with his bow tie. He distracts himself with food, and he holds the black gavel of judgement to feel superior to others that might hurt him (after all if he judges them first he cannot be rejected, or if he is rejected he can then judge them). His smile is manic, and he grins to try to get people to like him and to hide any negative feelings. His tentacles seek to ensnare people into his lives- maybe to discard them later and maybe because he wants to be in their lives regardless of their boundaries. Although I want to hate him, I know he is the parts of me that feel shame and exile. To be whole, is to love him. To love him, is to love the parts of myself I have tried to run away from.

Shadow Work Challenge Day #6:
Introspection- “What Do You Need to Work On”
Identify what aspects of your self could be improved by discerning which areas of your life you find disconcerting.

Oh man! I could be here all day. To be brief I need to work on my judgement of others, procrastination, ability to deal with shame and guilt, and deceit that I use to try to hide the things that are related to the preceding things listed.

Judgement- As said during previous shadow explorations – I can justify judging people. Judging others, in a messed up way, makes me feel better about myself. I was reading an article on how when a group “others” another group or person it makes them feel better about themselves. I have seen that true for me as well. I also need to acknowledge my wound at being judged by my weight, race, etc. I have some hurt there, that I need to address and heal from. Judging others also makes me feel like an “authority” from the place I am judging people from. For example, judging someone’s cooking might come from a place of “well, I know I am a good cook, so I have the right to judge what that person does”. Judging sucks. I am going to tackle these wounds associated with it and move on.
Procrastination- I hate this! I suffer from executive dysfunction to some degree. If there is a task I am late on, I will start to feel emotionally uncomfortable about that task and I will find almost anything else to do instead of that task. This is especially frustrating since doing the task will alleviate my anxiety! This is something I am getting better at as I learn to process my emotions better- but it still is a major problem and an obstacle to my success.

Shame & Guilt- My twins of agony! I still struggle with the shame and guilt of relationships I have destroyed, resources wasted, and people I have hurt. Recently I sent some apology letters to some people I have hurt, and there are more I need to write to help alleviate these feelings that I try to ignore. If I can find a better way to release and process these emotions- I can make a lot of progress.
Deceit- I grew up with an addict that was a pathological liar. That being said, I am old enough to know right from wrong, but the temptation to use that old programming to solve problems is hard to resist sometimes. I have come clean about a lot of things, and it is still sometimes a struggle to admit I do something as trivial as sneaking a candy bar when I am on a diet.

Shadow Work Challenge Day #7:
Critical Analysis- Dissect an Unhealthy Habit
Analyze a habit that serves as a distraction from yourself and/or impedes your well being. Ask yourself when you developed this habit, what caused you to develop it, and how it affects your life.

So let’s go with “procrastination” from Day #6’s challenge.

I literally waste time on things that will have no productive end. I like to excuse it as “everyone does it”, but that seems like a cop out. I waste the most of my time on things like wikipedia, browser games, or reading the news. I don’t think those things are bad in and of themselves. What makes it a bad habit is that I will use these things to distract myself from the emotions I am feeling. For example, if I procrastinate at work- I am avoiding the emotions that come with the fact that my job affects everyone else I work with and that my lack of focus can affect the wellbeing of others. If I procrastinate spiritual work, I may be avoiding emotions related to my sense of personal worthiness (“do I deserve to spend time on this?) or several other things depending on the work. So really looking at this- I need to get better at sitting with and processing my negative emotions based upon getting things done- on a case by case basis- until I can get the “spiritual waters” of my emotions in a better flow. I know some of that issue stems from the fact that I never was taught my emotions were valid as a child, and that I should value my mind over my heart. My family was very much into academic achievement over anything else, so like some gifted kids I poured my attention into studying in an effort to prove my worthiness to myself and my family. So to summarize here is my to do list I need to consider from this:

Accepting emotions about a task I want to accomplish
Confront my own negative emotions
Resolve childhood issues were emotions weren’t valued

I think the first two can be accomplished with more mindfulness and practicing being grounded. I already have been having some progress there For the last one involving childhood issues- I am going to tuck dealing with that into my “inner child” work that comes a bit later.

Shadow Work Challenge Day #8:
Emotional Awareness- Observe Your Unadulterated Emotions
Let your emotions flow freely today; don’t muffle them. Try to observe and understand them without judgment. Don’t escape, express. Don’t deny, accept.

Dammit, I knew this was going to be hard for me. I was going to do this kind of stream of consciousness and write to document emotions as they happened. I tried that on Saturday, and I failed pretty miserably. So I tried again on Sunday. The challenge was that as I was feeling the emotions as full as I could, I ran smack against my value of being emotionally responsible and trying not to dump all my emotions on the people around me. I struggle with this- finding the balance between being authentic with who I am and not having “emotional vomit”. I think the balance comes from respecting the boundaries of the people around me. Because I didn’t grow up with anything near good boundaries, this can be a challenge for me. When I was trying to talk about my emotions, I found that talking about them didn’t help all the time, so I realize I need to go back to other ways of processing emotions. I used to write tons of poetry, and I realize how useful that was for helping me process things. I guess I know what habit I am going to go back to.

Shadow Work Challenge Day #9:
Write a short [creative] story based on some sort of dilemma you are currently experiencing.

Looking at this work, I realize that how I work through these challenges says a lot about me as much as the challenge itself. I like to think of myself as a “writer” and as such I thought this would be an easy challenge. Then it dawned on me I didn’t know what dilemma to address. Should I talk about my suicidal thoughts that happen at my darkest times? Should I talk about my struggles to fit in and not feel like I belong? Then I thought that one of my goals for doing shadow work is so I can function better in day to day life. One of the most crucial problems I have was actually illustrated in my problems completing this challenge- that of indecisiveness and executive dysfunction. My short story below illustrates this dilemma. On a magickal note, writing a short story like this is the basis for many of my “writing spells”, and as such this story is also a magickal working.

It was Tuesday. Marcus had survived the hectic horrors of Monday, while having a medical deficiency in vitamin C(affeine) and battling the usual cocktail of anxiety and mental health issues he wears like a worn, wool sweater- comforting in its familiarity, but still irritating. In his office he was staring at the walls and felt trapped in a web of anxiety and indecision- he was both the spider that made the web and the fly trapped within it. There were clients to call, quotes to send, and not to mention all of the personal work he needed to do at some point- journaling, research, and various projects. There was so much to do, and as his mind raced over all of the different things to do, he realized that he could not prioritize what to do first, Everything seemed equally important. The anxiety felt like a weight in his stomach and a pressure on his brain. The feelings built, and every minute seemed to add another layer in the way that an oyster adds layers to the irritation of a grain of sand and builds a pearl.

Marcus went outside. The cool air seemed to soothe him. He breathed slow and began to ground- imagining his feet were roots and his arms were branches. The anxiety started to subside and he started to feel some sense of peace. His vision relaxed and he began to stare into the sky while his body relaxed. The clouds in the sky sailed in the wind, being kept company with a flock of crows. The murder of crows flew closer to Marcus, and one of the broke off from the rest and came closer to him. The crow eventually landed next to Marcus, closer than any bird had ever been to him and it opened its mouth as it was speaking.

“Hello, Mr. Crow,” Marcus said.

“Hello, yourself little human,” the Crow replied.

Marcus was frozen in astonishment. The crow preened and cleaned itself for a moment, and then stared at the confused man. “Listen, we saw you in the distance and we couldn’t help but see that you seem to be going through some stuff. Do you want to talk about it?”

Marcus was still stunned, but he gradually came to accept this new doolittlesque reality. “I have a lot on my mind. I have so much to do and people are counting on me. I get overwhelmed sometimes.”

Crow nodded. “It is fine to feel that way, and sometimes you just need to walk away and get your bearings. Come fly with me and see what I mean.”

Marcus raised an eyebrow in disbelief. Talking crows were one thing, flight was another. Before Marcus could argue, or disapprove- he already felt his fingers curve to talons and the hairs on his flesh expand into feathers until he had successfully changed from an anxiety ridden middle aged man to a crow. “Now, let’s fly!” cheered Crow.

Crow and Marcus flew over the tops of buildings and if their wings were drums, they would have beat a song of freedom and release. Marcus’ only thoughts were of the air and freedom. HIs worries flew into the clouds, and any doubts and anxiety drifted away. Crow said, “Feels good doesn’t it, but it works up an appetite. Follow me.”

Marcus and Crow had flown several miles to where the town blended into more rural dwellings and small homesteads. They landed by the side of a road. Marcus started to smell something sour, but oddly mouth (I mean beak) watering. They stopped by the side of the road and there was a freshly run over squirrel. Crow said, “Let me offer you lunch, but first a few words. Great Spirit, may this squirrel dance with you in its journey and be given the peace of Death and the glory of Rebirth. We thank you and this squirrel for this meal and our lives.” With that, Crow began to peck at the small woodland morsel to his heart’s, and belly’s, content. Marcus was thinking to himself that there was no way that we would do this, but something drew him to the squirrel and he could not help himself. As Marcus ate, he asked Crow, “I didn’t know crows prayed before they ate.” To which Crow replied, “Of course I do, don’t you give thanks also?”

After their meal, they flew to the murder of crows that Crow was a part of. They heard the crow stories that men do not know- how the crow impersonated one of Odin’s ravens and caused much mischief, the tale of the golden feather, and even a smattering of the great epic of the Ballad of Broken Sky that even young crows are told bits of while still in the nest. Marcus turned to Crow and said, “Sometimes you just need to live and be and let things happen where they may. You have a lot to do, mighty human, and sometimes you need to acknowledge what you are feeling and let it go.”

Marcus and Crow flew back to the building that their journey started at. Marcus bowed to Crow and said, “Thank you. I needed the relief and I needed some perspective.” Crow bowed in return and flew off squawking, “Anytime, brother. “

Marcus woke up outside his office in the same spot he had left. His arms felt oddly sore, but his mind and body otherwise felt at peace. There were reports to write, clients to cajole, and projects to complete- but he knew that things would fall into place as long as he could get some perspective sometimes.

Shadow Work Challenge Day #10:
Artistic Expression- “Illustrate your Fears.”
Using an artistic medium to illustrate your fears and how they make you feel.

I don’t have a lot of physical fears. I am not afraid of spiders, or snakes, or heights, or anything like that. My fears are purely existential. One of my fears is loneliness and abandonment. They are really tied together and born from the same root of childhood abandonment. It leads to a lot of my depression and can be the cause of some of my acting out when I am on a bad mental health spiral. This deep sense of loneliness feels like a prison and at the same time shuts me off from others like a cage. Loneliness feels like death. My other fear is that of being forgotten, not having an impact, and not mattering. Part of that comes from worthiness issues- as in I do not feel like I matter and I need to prove my worth to myself and others so that I have a right to even exist. The other part of that is not a fear of physical death, but the death that comes from being forgotten. When my grandmother passed away (the one that raised me), I was left with a lifetime of her mementos and belongings. Many of them had to be donated or given away, and I was left with this question “Is this all we are- stuff we leave behind?” I think of that sometimes when I have suicidal thoughts- I think of the stuff my loved ones will go through and how things that mattered to me might just be carelessly thrown away. Of course we are more than that, and our legacy is the impact on others. At the same time, I still fear “Did I do enough good things to matter to those that I leave behind?”

Shadow Work Challenge Day #11: Map Out Your Dissatisfaction
Write down any areas of dissatisfaction in your life. Try to map out what these dicontenting circumstances stem from and what they branch out to.

I am going to make a trusty Venn diagram for this, and then explain it. The three major areas of my dissatisfaction are Relationships, Money, and Time.

A lot of my relationships with these things come from the obstacles I have to deal with and my dysfunctions. Although I am a lot better at the things that hold me back (i.e. with mental illness- I have therapy every 2 weeks, I meditate, and I do things to manage my stress more), they are still there. An old adage is “it takes time to have time”. I find that true since I need to take the time to do the little things, and not resent them with the thinking that the self-care and maintenance things are taking time away from me. In fact, they allow me to be healthier so that when I do need to accomplish something- I have more mental energy, clarity, and focus.

When I manage my time and money better- I feel abundant. When I have the money to invest in my relationship- I can have meaningful experiences that bring me closer to that person (i.e. saving up for a cool date with my wife) and ones that make me feel good about living. When I manage my time well and focus that on my relationships- I can build healthy intimacy. All of these things in concert bring me joy and help me deal with the things that get in my way- and I can start a positive feedback loop. It is this feedback cycle that has really been helping me get my head above water on all of this work. Those positive feedback cycles are a key component in spiritual alchemy and are tools to be cultivated.

Shadow Work Challenge Day #12: Asses Your Core Beliefs
Analyze your fundamental beliefs. Ask yourself if these beliefs are reasonable and worth keeping or if your life would improve if you were to eliminate them.

Instead of listing my values and ethics in a clinical and mental way (which was my first reaction), I am going to delve a little deeper into beliefs I have about the world that are a little deeper. I will sort them into positive and negative ones. I realize by doing this how they conflict with each other and cause little “short circuits” in my life, and if I can deal with those destructive beliefs- I can deal with my anxiety and mental health baggage much better. A lot of my negative beliefs come from trauma, and my positive beliefs are actually well grounded and realistic.


I will never be good enough for the love I want
Anything that makes me happy will only be brief.
I will always be broken.
I will always be burdened by the bad things I have done in the past.
I will always feel lonely.


I am fundamentally a good person, but my wounds and trauma cause me to act out in destructive ways.
Happiness is an emotion- the goal is peace, balance, well-being and promoting that within myself and the world around me.
I can heal, even though it may take longer than I wish.
I am surrounded by people that actually care about me.
It is ok to be alone, when I need people they are actually there for me when I reach out.

Seeing all of this laid out is actually more helpful than I thought. This will really help me in the last two challenges of the original 14 and the work I want to do after that. This perspective can really help me when I am spiralling at my worst times.

Shadow Work Challenge Day #13: Artistic Expression- “Forge Your Shadow”
Create a poppet that represents your shadow. While making it, project onto it all of the shadow aspects you have explored in the past twelve days, as well as any others.

About five months have passed since the last challenge. A lot happened to me between the last challenge and this one. I hit a very hard wall, and I hit rock bottom with the most shameful manifestation of my shadow- my sex addiction. It almost destroyed me and my family, as untreated it has destroyed many relationships- personal and professional- in the past. My addiction comes from my trauma directly. I tried to fill my wound with destructive behavior. To regain my sanity, I had to have a psych evaluation, get new medication, go to therapy, and go to a support group 1-2 times a week. I am doing much better now. All of the work before this created pressure within me that helped me explode my ego like a volcano. I feel better than I have in years.

My poppet is a “shadow golem”. Like the artistic expression from Challenge #5, he has a gaping wound and tentacles. The wound hollows him out and reflects the emptiness he feels. The tentacles are his unhealthy way of trying to ensnare others so that he is not alone.

Shadow Work Challenge Day #14: Meditation- Embrace Your Shadow
Meditate with your shadow poppet. Visualize it being encompassed by white, healing light. Direct as much love and acceptance towards it that you can possibly muster.

After all of the other work I did, I was really prepared for this. I had separated my shadow from me in order to understand it. Now was the time to rejoin with it. I have to love my shadow. By loving my shadow, I am learning what it means to unconditionally love myself. After I meditated with my shadow, I started dreaming of him. The most powerful dream was of my shadow as a dark, shadowy kid version of myself. He was left to play in a storage room by himself. His mother had abandoned him and he was sad, rejected, and lonely. I talked to him and gave him the biggest hug I could. Then I played a game with him until he started to smile.

During this process, I learned that the process to understand and re-integrate, love, and learn from my shadow is its own alchemical process. I will talk more about the shadow and alchemy in another post. For now, I have a peace and self-acceptance I have never known until now.

Shadow Work Challenge- Epilogue on 14 Day Challenge.
While I have enjoyed these challenges- they are really the precursor for me for even deeper work that uses the summation of what I have learned about myself and spiritual techniques. These 14 challenges have shown me a lot more about myself, who I am, and what I need to change than I honestly could imagine. I hope my journey inspires and helps your own.


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