Shadow work involves examining our personality flaws in an attempt to understand ourselves better. It's tough work but hugely beneficial. Psychologist Stanislava Puač Jovanović shares 31 shadow work prompts you can ask yourself to get started with the practice.


The Shadow is the part of ourselves, according to K. G. Jung, that represents our dark side. It holds all the morally reprehensible tendencies we wish we did not have. However, it also hides many of our qualities, capacities and potential.


Shadow work means increasing awareness of your thoughts, feelings and actions. Moreover, it requires you to become brutally honest with yourself and not criticize or condemn. You will need to practise self-compassion and learn to own your weaknesses, not project them onto others. Therefore, even though it may sound simple at first, shadow work is a quite psychologically challenging journey. 




For this reason, we may need some shadow work prompts to help us out on this road. This article will explain why you need them and what you get from shadow work prompts. We will talk about how to use these shadow work prompts and offer a few possibilities you might want to pick from when embarking on your psychological journey to self-awareness. 


Why do we need shadow work prompts?

First, let us be clear on why we need to travel to the dark caves of our subconsciousness and search for the monsters there in the first place. 


Since you are reading this, I will assume you do have a desire to understand yourself better. You want to be a complete person. And to be one, you need to embrace all of your sides — the good and the bad. In Jung’s words, we may not become enlightened by imagining figures of light. We become enlightened by making the darkness conscious. 


“Shadow work prompts will give your search for self-awareness some structure. They will lead you through the thick underbrush of your mind.”


And precisely here lies the reason why we need shadow work prompts. Our subconsciousness is uncharted territory for us. Scientific research demonstrated that our unconscious mind guides our perceptions, evaluation, and motivation. Even though others may notice the Bad and the Ugly in our actions, as a rule, we remain ignorant of what we hid from our consciousness. 


So, you need guidance on the path of personal investigation. Shadow work prompts will give your search for self-awareness some structure. They will lead you through the thick underbrush of your mind. 


How to use these shadow work prompts

Shadow work is as distinctive as every individual. That is, there are no absolute rules you need to follow. It is your personal journey. You will do best if you follow the unique guides that appear on this path. 


Nonetheless, you should consider a few valuable tips for using shadow work prompts.


First, take it slow. Shadow work prompts will take you into rather heavy topics. Remember, the Shadow is the side of yourself you are not keen on. So, to avoid ruminating for hours about what you discover about yourself, think about writing or meditating about one shadow work prompt at a time. 

Explore shadow work prompts with journaling


At the same time, make shadow work a regular practice. Similarly to psychotherapy, this form of self-exploration requires commitment. Indeed, research shows that regularity is a necessary element of therapeutic growth. 


You may want to come up with a centring ritual as a beginning of your shadow work for the day. It can be anything from taking a walk, meditating, doing yoga, having a quiet cup of tea, or lighting a candle and saying an affirmation. 


Finally, trust your psyche to take you where you need to go. Shadow work prompts are likely to take you places you have tried to avoid for your entire life. Still, remember — to be whole, you need to recognise and accept every corner of your psychological existence. So, let the thoughts and words come to you. Write or think freely, without censorship. 


Things to hold onto while reflecting

Shadow work prompts will trigger an avalanche of insights that most likely will not feel comfortable. Even though you might have been preparing for this, you may learn that you possess the traits you despise the most in others. Such knowledge could shake your self-image, at least at the beginning of the process.


Because shadow work is supposed to take you on a path of psychological growth (and not be an arena for self-loathing), remember to lean into these three core principles:


Self-compassion Be kind to yourself. What you are really learning is that you are a human, nothing more. No one person is perfect. Embrace the fact that you have flaws, and applaud your courage to look them square in the eye. 

Passive observation Do not judge what you are learning about yourself. Simply recognize the thoughts and insights that are coming to you after you employ the shadow work prompts below. You are here to explore, not to moralise. It is precisely your attempt to comply with cultural, social and moral norms that caused the creation of the Shadow. 

Honest reflection/documentation All the work you are about to do is not worth the time if you are not honest. Indeed, make sure you are completely honest. It will be a bit ugly at times. But the only way to make shadow work truly worthwhile is if you are frank with yourself. 

Answering shadow work prompts will reveal the devil inside shutterstock/ra2 studio


31 shadow work prompts

At this point, decide if you are going to journal (which I recommend) or merely reflect on these shadow work prompts. Pick the time and the settings in which you will commit to shadow work. 


“Shadow work prompts will trigger an avalanche of insights that most likely will not feel comfortable. Even though you might have been preparing for this, you may learn that you possess the traits you despise the most in others.”


When you're ready, go ahead and delve into these shadow work prompts. Also, feel free to journal in freestyle whenever you feel like it. These prompts are meant to trigger your reflection and help you notice the areas in which the “monsters under your bed” might be hiding. 


So, a river of thoughts and associations may follow. Note down whatever you notice and let the process of self-discovery evolve on its own terms.


Family and childhood shadow work prompts

  1. How are you similar to your mother, father and family members/caregivers? How does this make you feel?
  2. How did your caregivers comfort you when you were upset as a child? Do you do something similar when you or someone close to you is upset?
  3. What irritates you the most about your mother/father? Do you manifest the same trait, and when?
  4. Remember an event from your childhood that made you feel insecure, unloved or scared. In which situations do you feel similar, now as an adult?
  5. What is your most traumatic experience from childhood? How has this experience affected your actions and perceptions as an adult?


Romantic relationships shadow work prompts

  1. Do you have patterns in your romantic relationships?
  2. Are/were you in a relationship that seemed familiar to that between your parents?
  3. Which of your father’s/mother’s traits do you expect from your romantic partners?
  4. Do you behave like your mother/father in romantic relationships?
  5. What do you not forgive in romance? Why?
  6. How do you behave when there is a conflict in your romantic relationship?


Friendship and social relationships shadow work prompts

  1. What is your best friend like? Why did you pick them to be your best friend?
  2. What irritates you about others the most?
  3. What do others say about you that is not flattering? How much truth there is in that?
  4. In which situations are you misunderstood/disregarded/ignored?
  5. What valuable traits do others have, and you do not?
  6. What emotions are you afraid to show to others?
  7. Who do you hate to disappoint? Why?


Self-image and behaviours shadow work prompts

  1. When did you not act like yourself? What made you act that way?
  2. When were you most embarrassed about yourself? Why?
  3. When were you in denial?
  4. What was the biggest lie you ever told? Why?
  5. What triggers you to act aggressively, to act out, to become disproportionally sad, to act impulsively?
  6. Do you feel like an imposter? In which situations?
  7. What is the worst thing you have done? Why? How do you feel about it now?
  8. When are you most envious? Why?


Takeaway: freedom through self-acceptance

Let me return to Jung’s quote at this point. In Modern Man in Search of a Soul, he wrote: “How can I be substantial if I do not cast a shadow? I must have a dark side also If I am to be whole.” Shadow work prompts are there to take you to the place of wholeness and freedom. 


They may not be pleasant to go over. Still, know that no alive person is immaculate. Remember the other quote from Jung? To paraphrase — you will not become enlightened by ignoring the darkness. You need to bring the hidden monsters to light. Only then can you address what you do not like about yourself. Only then can you make choices to do better or to change.





Freedom will come with the acceptance of who you are as a whole person. Learn the good, the bad and the ugly truths about yourself. Accept them and be free to be whoever you now choose to be.  

Main image: shutterstock/Juice Flair | The fine art of being: learn, practise, share

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Written by Stanislava Puač Jovanović

bert.jpgStanislava Puač Jovanović has a master’s degree in psychology and works as a freelance writer and researcher in this area. Her primary focus is on questions relating to mental health, stress-management, self-development and well-being.



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Thank you. This was helpful to my heart.

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Nice atricle

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