Shadow Work Challenge by UNMASKING THE DIVINE

I’m gathering all the pieces of this challenge here in one post so they don’t get lost in my endless tumblr stream of likes and reblogs. To see the original posts, please visit unmaskingthedivine.


In this shadow work challenge, we will be exploring our past and delving into some of the core experiences that have helped create and reinforce our shadows. Please keep in mind that shadow work is a highly individual process and there is simply no way I could ever devise any sort of curriculum that yields impeccable results for everyone. It is up to you to give this challenge true substance. This is not a set of step-by-step instructions or specified exercises, but a collection of interrelated subjects that form a generic basis for shadow work that you will [hopefully] be able to build off of.

The prompts included were designed to be responded to in one (or all) of the following ways: journaling, creative expression, or tarot reading. I recommend journaling and/or creative expression as the basis with tarot as a supplement, but it can serve as a stand alone tarot evaluation as well (which is why I created this Tree of Life Spread). Whatever works for you, go for it! This challenge is only meant to get your mind reeling, and as you will see it’s pretty cut and dry, so I encourage you to use it as you please– get creative and allow it to evolve as you go. If you feel comfortable doing so, please share your work and tag “january shadow work challenge”. I for one would love to see it, and I’m sure those who are trying to get their foot in the door with shadow work would appreciate some reference material. In any case, I thank all for participating and as always I welcome public or private feedback!

(P.S. I did not get to work on/edit this as thoroughly as I would have liked, so please forgive me for any errors or sloppy writing in general! Also, feel free to shoot me an ask if you have any questions. Best Wishes and Happy New Year!)

Shadow Work daily prompts

Shadow Work daily prompts

Day 1: Preparation + Light Work

We will kick off this challenge with a day of preparation and light work.

Take some time to relax. Mentally prepare yourself to experience some discomfort. Charge yourself up. Drink a lot of water.

Ponder your life. Pay tribute to the things you’re grateful for– the experiences you’ve had, the people you’ve met, the things you’ve achieved. And don’t forget to include yourself! Regardless of what you’ve been through or what you’ve done, you’re an fascinating human being, a world all your own. Give yourself credit just for being alive.

Count your blessings and keep them in your thoughts today. Write them down or use an artistic medium of your choice to express them creatively– this could be as simple as a quick sketch, some snapshots, a short poem, or even a compilation of relatable art created by others (think photos, music videos, gifs, etc). Work with whatever feels right, just make an effort to actively draw your attention to the positivity and abundance in your life.

Tarot Question: What aspect of myself can I rely on to facilitate this month’s shadow work?

► Day 2: Childhood – The Birth of the Shadow

Infancy, childhood, and adolescence all set the stage for the development and reinforcement of the shadow. For the sake of brevity, I am using the term ‘childhood’ to cover all of these life stages, however. Bear that in mind whenever I refer to childhood throughout this challenge.

Trace back your memories as far as you can. Try to overview your early life in as much detail as possible. Articulate or otherwise express how you experienced childhood as a whole. Heed to any areas of resistance you encounter. Note pivotal turning points or memories that stand out. Attempt to recall the first time you experienced emotions like sadness, anger, jealousy, anxiety, remorse, and contempt.

Tarot Question: What facet of my childhood have I overlooked or otherwise need to reevaluate?

► Day 3: Home Life – Security, Belonging, Self-Worth

Home life is closely tied to one’s sense of security, belonging, and self-worth. By analyzing the condition of the home life we experienced during childhood, we can shed light on how these aspects of ourselves developed.

Reflect on what your home life was like growing up. Consider things like household income, inter-family relationship dynamics, overall lifestyle, etc. Was financial stability a source of stress? Was the relationship between your parents conflicted? Did you feel accepted by your family? Did you feel safe at home? Did you live a life in a suburban setting, in the boonies, in an orphanage?

Tarot Question: What aspect of my home life might I benefit from taking into consideration?

Note: Keep in mind throughout this challenge that even positive experiences can contribute to the shadow. For instance, say you experienced a home life that you perceived as being so close to perfect that now, in your adult life, you experience a great deal of difficulty and stress because you feel obligated to recreate that same quality of life for yourself and your family.

► Day 4: Mother – Needs, Trust, Love

The traditional mother figure can be associated with needs, trust, and love. As infants, we typically rely on our mothers to meet our needs, we have no other choice but to trust that she loves and cares for us enough to accommodate those needs. By looking at the role our mothers played in our lives we can gain a sliver of insight on how we go about meeting our needs, establishing trust, and receiving/expressing love.

Consider your mother (or other persons who served as a mother figure). What is your relationship with her like– what was it like growing up? Take note of any striking memories. How do you see her? In what ways do those qualities reflect in your life? Do you experience any resistance to your mother? Think about the things you don’t like about her, then ask yourself how you might demonstrate those qualities yourself. Consider the things you do like about her and what lengths you might go to to cultivate those qualities in yourself.

Tarot Question: What element of the mother archetype might I benefit from considering?

Note: Parental figures may be interchangeable. If you were raised by a single mother then she likely played both the mother and father roles in your life to some degree and you might find it helpful to contemplate those aspects of her separately. Likewise, you may have been raised by multiple people, in which case you might benefit from factoring them all into the equation. Shadow work is unique to each individual, so this challenge may seem rigid for some, but it can be adjusted fairly easily.

► Day 5: Father – Guidance, Protection, Discipline

The father figure can relate to guidance, protection, and discipline in a traditional sense. We rely on our fathers to provide a sense of safety and security. We learn discipline through him, not necessarily by way of punishment, but by observing his efforts and heeding to his wisdom.

Think about your father (or other persons who served as a father figure). What is your relationship with him like– what was it like growing up? Take note of memories you have of him that stand out. How do you see him? In what ways do those qualities reflect in your life? Do you experience any resistance to your father? Consider the things you don’t like about him, then ask yourself how you might demonstrate those qualities yourself. Consider the things you do like about him and how far you might go to embody those qualities yourself.

Tarot Question: What element of the father archetype might I benefit from considering?

► Day 6: Siblings – Fellowship, Competition, Cooperation

Siblings (or other close childhood companions) typically provide early experience with fellowship, competition, and cooperation. We learn both rivalry and comradery through this type of relationship. By dissecting the relationships we had with our siblings (or peers), we can reveal how we relate to and interact with our counterparts.

How many siblings do you have, if any? What is your relationship with each of them like– what was it like growing up? How are they mirrored in your life? If you don’t have any siblings, reflect on how being an only child impacted you and consider any cousins or friends who you might look at as siblings. Did you ever butt heads with these individuals? Did you look up to them? Did you ever experience a feeling of inferiority or jealousy in regards to any of your siblings or peers?

Tarot Question: What element of my childhood companionships might I benefit from exploring?

► Day 7: Assimilation + Light Work

One week down– congratulations! Now it’s time for a brief respite. Take some time to unwind and internalize what you’ve dug up so far. Think about how the awareness of some of the not so pleasant things you may have discovered about yourself can be used to better your life in some way.

Contemplate how all of your experiences, both positive and negative, have shaped you– for better or for worse. Appreciate your existence. Write down or otherwise express the things about yourself you’re proud of, no matter how small.

Tarot Question: What [positive] aspects of myself am I overlooking or taking for granted?

► Day 8: Upbringing – Values, Interests, Conduct

Upbringing generally seems to have a great deal of influence on the development of our values, interests, and conduct. By reflecting on the way we were brought up, we can get to the core of many inclinations, tendencies, and behaviors we exhibit.

Consider how you were raised. How were you expected to behave? What was considered “normal” in your family unit? What sorts of ethics were instilled in you? Were you ever drawn to or fascinated by things that were not accepted in your family? Note any resistance you experienced to the way you were raised.

Tarot Question: What aspect of my upbringing might I benefit from taking into consideration?

►Day 9: Culture – World View, Perspectives, Taboos

In a way, the culture we grow up/live in takes deeper roots than the more personal influences we’re exposed to in the sense that it is a collective influence that stretches across an entire populace from the past into the future. Culture generally sets the stage for the development of religion and societal standards and more or less dictates the way the family unit functions in many cases.

Consider how your culture has shaped you. Are you familiar with cultures abroad or have you only intimately experienced the one you were born into? How did you experience the culture you grew up in– did you feel comfortable being a part of it or did you feel out of place? What were the social boundaries and general etiquette like? What kinds of actions were considered okay and not okay? Were there ever any cultural taboos that had a particular impression on you? How have these factors impacted your experience with culture now?

Tarot Question: What aspect of my cultural conditioning might I benefit from taking into consideration?

►Day 10: Religion – Beliefs, Ideals, Morality

Religious background tends to have a tremendous impact on many individuals. It typically influences the system of beliefs we develop, the ideals we uphold, and moral code we adhere to. Though religiousness may beneficial in many respects, the sensationalized dogma that often accompanies it can have a particularly repressive effect.

Reflect on your religious background. How devoted to religious and/or spiritual practices were you/was your family? What sort of ideals were upheld? What was considered right and wrong? What was the underlying theme that accompanied the concept of religion for you– how did it make you feel? Did you find it comforting, assuring, manipulative, foolhardy? How did your religious background make you feel as a person? How have these factors impacted how you experience religion now?

Tarot Question: What aspect of my religious background might I benefit from taking into consideration?

►Day 11: Society – Status, Roles, Standards

Society has an infamous tendency to instill rigid conceptualizations of things like career status, gender roles, and living standards in us. Often times, these expectations become a burden and can create a lot of internal resistance to oneself.

Think about the society you live in and how it has shaped you. Are you generally accepted in society? What kinds of status, roles, and standards has it placed on you? How is your current career perceived? What role do you play in community affairs and family relations? How is your sexuality or relationship status judged? What kinds of living standards are you expected to uphold? Do you have any resistance to the expectations that have been imposed on you by society?

Tarot Question: What aspect of my societal influence might I benefit from taking into consideration?

►Day 12: Prominent Experiences – Perspective

Today we’re going to revisit some of the fundamental experiences that have helped direct the development of our various complexes. Key experiences we’re looking for here may likely be traumatic, possibly even repressed, so please keep this in mind. As difficult as it may be, analyzing memories of such experiences is vital– past traumas have an infectious way of seeping into the present, pervading our lives long after the experience occurred, hence the need to probe them. Of course, some of our most prominent memories may not always be so severe, however. “Positive” experiences commonly lead to shadow aspects as well, often influencing the conception of idealistic expectations that incite disappointment / shame / frustration when not met.

Recall notable past experiences, anything you feel has had a significant impact on you. Describe these experiences– how have they affected you? In what ways has your life changed because of them, directly or indirectly? Allow buried memories to resurface. What makes you afraid of or resistant to experiencing and processing the feelings associated with those memories?

Tarot Question: What past experiences have I repressed (or glorified) that I need to heal from (or evaluate)?

►Day 13: Assimilation + Light Work

Spend some more time reflecting on what you’ve discovered. Think about how you can apply what you’ve learned to your life constructively. But more importantly, set aside some time to relax.

If you’ve been digging deep these past two weeks you may feel frail, exposed, and vulnerable. That’s okay. Vulnerability isn’t as awful as it’s made out to be– it has its own gifts. So embrace it, seek to empower yourself through it.

Create a comforting environment for yourself where you can sprawl out and just be. Make a couch fort, run a hot bath, sneak off to the woods, lock yourself in your bedroom then light some candles and put on some music, whatever tickles your fancy! Retreat to this safe place and enjoy the feeling of comfort and solace– instill this feeling in the center of your being, concrete it there and try to mentally return to it in times of distress.

Tarot Question: How can I bring more healing energy into my life?

►Day 14: Ego – The Shadow’s Antithesis

Ego begins developing right alongside Shadow, but because it is how we consciously identify/portray ourselves, it serves as the forefront of our character. Many times our upbringing, culture, etcetera has a great deal of influence on our self-image– we are defined by these things in a lot of ways. By looking at what we embrace and own about ourselves we can see the intent or shadow behind it.

Contemplate your self-image. Do you notice your personality change depending on your environment or who you’re interacting with? Why is this? Express how you generally see yourself. What qualities are you proud of possessing? What shortcomings do you openly admit to? Ask yourself why it’s okay to possess these qualities and shortcomings but not others. What experiences influenced the development of these personality traits?

Tarot Question: What quality of my self-image might I benefit from evaluating?

►Day 15: Fear – What We Lack

Needless to say, addressing our fears is an integral part of shadow work. It can be helpful to understand that fear ultimately stems from the experience of lack. A lack of acceptance might spur a fear of rejection. A lack of safety and security might translate to a fear of danger. A lack of freedom and/or expression might become a fear of authority.

Reflect on your fears. Try to discern the lack you experienced that birthed each of these fears into being. Did a lack of security incite a fear of instability? Did a lack of love create a fear of abandonment? Did a lack of communication elicit a fear of intimacy? What kind of harm has adhering to these fears actually prevented, if any?

Tarot Question: What fears might I benefit from considering?

►Day 16: Attachments – The Mother of All Heartache

While attachments are generally related to fear and lack in some way, we can also gain insight by reflecting on our experience with the mother archetype. We are quite literally attached to (or a part of) our mothers for the first nine months of our lives. Even once the physical connection is severed, we are dependent on her (or some other caretaker) to care for us– we rely on this figure to survive.

Identify your attachments. Are they romantic relationships, material wealth, comfort, excitement? Consider the fears you described previously. Are they are at all related to your attachments? Reflect on how your experience with the mother archetype may have contributed to the development of your attachments, if at all.

Tarot Question: What attachment(s) might I benefit from letting go of?

►Day 17: Aversions – The Father of Adversity

Aversions generally tie into fear and lack, just as attachments do, but on the other end of the spectrum– they are what we resist, rather than what we cling to. I relate aversions with the the traditional father figure because much of the underlying energy that comprises this archetype is in alignment with resistance. It represents an intense driving force, a source of discipline and protection.

Identify your aversions. Be careful not to confuse aversions with fears, however. They are inherently different in the sense that aversions are things you are offended or repulsed by to some extent, not things you’re necessarily afraid of. In what areas of life do you experience resistance? Do you steer away from social interactions, romantic pursuits, ambitious endeavors, starting a family? Consider the fears you described previously. Are they at all related to your aversions? Contemplate how your experience with the father archetype may have influenced the development of your aversions, if at all.

Tarot Question: What aversion(s) might I benefit from confronting?

►Day 18: Habits – The Binding of Kinship

Most habits are typically established as a reaction to similar or recurring experiences. They sometimes serve as way we relate to our peers and as such can sometimes be influenced by those peers, which is why I have [loosely] associated habits with siblinghood or companionship.

Contemplate your habits. Do you notice any underlying themes? Do your habits serve to maintain a sense of control (e.g. compulsiveness, authoritarianism, abusiveness)? To evade pain, boredom, and/or loneliness (e.g. drug use, fanaticism, promiscuity)? Or to uphold social norms and receive acceptance (e.g. workaholism, perfectionism, martyrdom)? Etcetera? Consider how your relationships with your siblings/peers may have contributed to some of the behaviors you’ve established. Did you ever feel you had to compensate for something someone else wasn’t?

Tarot Question: What habit(s) might I benefit from analyzing?

►Day 19: Assimilation + Light Work

Are you still hanging in there? This isn’t getting too drab I hope. Take some time to internalize what you have unearthed the past week. But also, make some time for yourself.

Wrap yourself in self-love today! Look yourself in the mirror and tell yourself, “I love you and I forgive you.” Do it again. And again. (The third time means the most.) Express all of the wonderful qualities you possess. Tip: If you’re having trouble coming up with things, ask someone to describe something they like about you. An outside perspective from a loved one is sure to give you a boost.

Tarot Question: How can I cultivate more self-love and acceptance?

►Day 20: Ambitions – Will / Fire

(Please ignore the elemental association if you’re not into that sort of thing.)

Analyzing ambitions is great way to discover what drives you, to realize what makes you want what you want. This can be useful in shadow work because some of our ambitions might be inauthentic, unrealistic, or compensatory, or otherwise in need of careful consideration.

Consider your ambitions. How do you want to live your life? What do you wish to embody? What do you want to pursue? Where would you like to go? And most importantly, why do you want these things? What is the buried intent behind them? Also, how do you act on your ambitions– are you adamant about directing your life and achieving your goals or are you relatively complacent and willing to just see where life takes you? Try to discern how you developed these qualities.

Tarot Question: Which of my ambitions might I benefit from reconsidering?

►Day 21: Thought Patterns – Mind / Air

(Please ignore the elemental association if you’re not into that sort of thing.)

Today we will focus on the thought patterns we exhibit. Thought patterns have the ability to dictate our lives for better or for worse. Fortunately, we have the ability to shape them. Assessing the way we process information, the recurring thoughts we have, and the internal dialog we experience can be helpful in understanding our perceptions and overall attitude.

Reflect on your thought patterns. What kinds of things dominate your head space? Do you find yourself obsessing or fantasizing often? Is there an underlying theme that accompanies the majority of your thoughts, like fear, anger, or even gleaming positivity? How do these patterns serve you? Consider how they developed.

Tarot Question: What quality of my thought patterns might I benefit from realizing?

►Day 22: Belief Systems – Emotion / Water

(Please ignore the elemental association if you’re not into that sort of thing.)

Like thought patterns, belief systems have an enormous influence on the human experience, which in fact serve as a precursor to the development of thought patterns. Our belief systems serve as a way for us to make sense of the world and navigate through it, but they also often impede us. By evaluating our belief systems we can discover and work toward resolving any facets that are harmful or inhibiting.

Ponder your beliefs. What do you believe is the purpose of life? Do you believe in an afterlife or reincarnation? Are you strictly devout to the teachings of science or do you look to religious dogma to understand existence? Or do you only hold merit in you personal experiences? How did you develop these beliefs? Why are they important to you?

Tarot Question: What aspect of my belief system might I benefit from contemplating?

►Day 23: Desires – Body / Earth

(Please ignore the elemental associations if you’re not into that sort of thing.)

Similar to ambitions, but geared more toward instant gratification, desires drive us. Whether they drive us to fulfill them or to evade them, they have force. Desires serve to fill that insatiable void that we all seem to feel deep down (you know what I’m talking about). Of course, this does not make them inherently bad, it just makes them a prime subject of scrutiny for shadow work.

Think about your desires. What do you long to do on a regular basis? How much influence do your desires have over your life? To what extent do you go to meet them on a regular basis? Do you consider desires the “root of all evil” or do you believe they should be freely indulged? Why do you think that way? What experience have you had with your desires?

Tarot Question: Which of my desires might I benefit from exploring?

►Day 24: Current Condition – The Weight of the Past

All of the topics we’ve delved into during this challenge have played some part in what we’re experiencing today, right now. The past creates the present, but it doesn’t have to dictate it. You can create your own ‘luck’, so to speak. As we address our current condition with this new perspective we begin moving forward in awareness, slowly lifting the weight that our past experiences bear down on us.

Contemplate your current state of being. How have you been feeling mentally, emotionally, physically, and spiritually? How well have you been dealing with life? Do you have any complaints or worries? Consider how the various life factors you’ve reflected on this month have influenced your present experience. Do you see a ripple effect or similar experiences repeating themselves?

Tarot Question: What quality of my current condition is being most heavily impacted by my subconscious?

►Day 25: Assimilation + Light Work

You’ve come so far! Contemplate the past week’s work– try to piece the puzzle together, so to speak. Also, please spend some time appreciating existence. It’s not all bad, ya know? In fact, it can be pretty great. Do something that makes you smile, or even better, do something that makes you laugh.

Look for the abundance in your life. Describe, depict, or otherwise express the things you are grateful for. Spend some time with loved ones. Breathe in the love that surrounds you.

Tarot Question: How might I cultivate more abundance in my life?

►Day 26: Relationships – The Mirror

Everything we’ve covered this month ultimately leads up to this. How we relate to others has so much more to do with our own internal experience than with the other person and being aware of this can ultimately transform you and your relationships with other people and the world around you.

Reflect on various relationships– from romantic to platonic to family to professional, even notable interactions with strangers. How do you generally perceive people? Do you hold onto preconceived notions? Is it difficult for you to maintain relationships? How have you experience your sexuality? Does intimacy make you uncomfortable? Do you find it difficult to trust people? Consider how do your relationships mirror your internal condition.

Tarot Question: What about my relationships might I benefit from evaluating?

►Day 27: Projections –  The Faults We Find

Projections occur when we attribute denied aspects of ourselves to others, whether they do in fact possess the same qualities or not. Projections are typically disparaging or condemnatory in nature.

Take note of how you project yourself onto others. Even when this challenge is over, I want you to try to remain conscious of your projections. What bothers you about others? What are your pet peeves? What are your complaints? What sorts of things in the world provoke reactive emotions?

Tarot Question: What do my projections reveal about me?

►Day 28: Reflections – The Beauty We See

Reflections are the inverse of projections. When we observe something admirable in another person it is typically an understated quality of ourselves we are seeing reflected in them. Reflections are generally attractive or commendable in nature.

Notice your reflections. Even when this challenge is over, always try to remain aware of your reflections. What qualities do you admire in others? What attributes do you wish to embody? What do you envy in others? What about other people or the world in general inspires you?

Tarot Question: What do my reflections reveal about me?

►Day 29: Shadow – The “Other” You

Review all of the work you’ve done this month. Pay special attention to any underlying themes you’ve discovered or recurring reactions to similar experiences. Try to conceptualize how you can consciously incorporate your shadow aspects into your life in a constructive way.

In light of everything you’ve discovered, how do you see your shadow? What aspects of yourself have you repressed? What are you avoiding? How is your life influenced by your subconscious? What kind of relationship do you have with this facet of your psyche? How do you think your shadow sees you (i.e. your ego)?

Tarot Question: What aspect of my shadow might I benefit from working with?

►Day 30: Working Toward Integration

Unveiling the secrets hidden within the subconscious is only the first step in shadow work. It will take repeated introspection and continued effort to apply what you’ve learned to your life in a constructive way. Continuous confrontation and conscious reprogramming will be required to make a noticeable change. But it’s worth it. Working with shadows is an invaluable and highly rewarding journey, treacherous as it may be at times. Keep treading forward. Never quit seeking to understand your behavior, motives, and emotions. Remain objective and observant as often as possible.

Today we will take some time to brainstorm. Reflect on everything you’ve covered this month. Devise ways you can go about actively resolving the issues you know you need focus.

Remain mindful of your thoughts, emotions, and behaviors, but not just today– strive to be self-aware on a daily basis. Look for your shadows. Every moment is an opportunity to learn something about yourself and to ultimately better yourself and the world as a whole. Take small steps, but take them steadily. With some patience, discipline, and determination, little by little you will work toward integration and alignment with your authenticity.

Tarot Question: What guidance do you have in regards to integrating my psyche?

►Day 31: Light Work

Congratulations! You did it! We’re wrapping up this challenge with a day of light work. So give yourself a pat on the back. Be proud of this accomplishment, as trivial as it may seem– you’re brave to have faced these things.

Reward yourself! Whatever that means for you (as long as it doesn’t jeopardize your mental/emotional/physical health, please). Have a drink, buy yourself a gift, have a fun night out, take a camping trip. Just enjoy yourself. Revel in the pleasantries of life; forget all the heavy stuff for a little while.

Tarot Question: What might I benefit from doing more of on a regular basis?


Tarot Spread for the Shadow Work Challenge

Tarot Spread for the Shadow Work Challenge

Oh! The amazing Benebell Wen has a Shadow Work Workbook too!


Marks will be awarded for participation

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