112 Shadow Work Prompts To Help You Tackle The Tough Stuff

Last Updated on April 17, 2024

When you think of the term shadow work prompts you might first think of the image of yourself cast by the sun. However, there is another meaning which comes out of the work of a Swiss psychologist named Carl Jung.

Jung’s work identifies something we all have called a shadow. The shadow is made up of all of the negative aspects of our personality. 

For example, character traits such as hatred, greed, selfishness, and envy would be part of the shadow.

In order to control and ideally rid ourselves of the negative aspects of our personality, we must first recognize them, and then work to control them.

Journaling is an ideal and effective way of dealing with one’s shadow self. Through thought and reflection, and then writing about these thoughts, we can achieve recognition and understanding of negative parts of ourselves.

Journaling also lends itself to goal setting and planning around how to deal with negative impulses we may have.

The prompts in the article can help you to begin this search of yourself, and help you to find healing, and a way forward through journaling.

Challenging Shadow Work Prompts For Beginners

In order to discover shadow parts of yourself, you must wrestle with some challenging questions.

This can be difficult. Searching our memories and the deepest corners of our mind where we have shelved painful and hurtful experiences can be emotionally hard and draining.

Yet, this is where we have to go if we are to understand why we perhaps feel angry, or unable to commit to a relationship, why we don’t show our true feelings, or why we are overly critical of ourselves and others.

The prompts in this list help you to get to the crux of the matter. You could begin the process by describing yourself objectively as one prompt directs.

Perhaps you want to follow the prompt which asks you what you are most afraid of, or maybe the prompt which asks you to identify when you have been self-sabotaging or destructive in your life.

Read through the prompts and select those that strike a chord with you, then begin with 

honesty to think and write.

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34 Challenging Shadow Work Prompts For Beginners

1. “What person has hurt you the most in your life?”

2. “Which traits would you least wish to be described as having?”

3. “Think of a relationship you’ve walked away from. Write down the reasons it’s been a positive life choice.”

4. “Do you generally feel less than, better than, or equal to others? Explore this.”

5. “Describe yourself with objectivity.”

6. “Do you similar trait or traits do you share with your parents or childhood caregivers?”

7. “Do you consider yourself to be confrontational? Why? Is this something you’re proud of or would you prefer to be different?”

8. “Think again about those memories of shame. Close your eyes and take yourself back to when you were at your very worst. Relive the feelings of that time. Now look around you and see how far you’ve come.”

9. “A journal open on a white desk with a pen and jar of sweets in the background.”

10. “Who regularly (or last) belittles or downplays your emotions?”

11. “What misconception do people have about you?”

12. “What memories bring you shame?”

13. “What is your definition of failure?”

14. “What most frightens you?”

15. “Nobody enjoys feeling hurt, anger, rejection, betrayal, jealousy, etc. What is the very worst emotion to experience for you personally? Why? Where does that come from?”

16. “Do you have healthy boundaries in your relationships?”

17. “A pink journal lays on top of a white notepad. There’s a pen on top of it and some pink confetti on the white desk beside it.”

18. “How do you think people see you?”

19. “List out your core values.”

20. “What makes you feel empty? How do you tend to fill that void?”

21. “Think about unhealthy relationships you have currently or have had previously. What’s the common theme?”

22. “Think about the people closest to you. What would you change about them, if you could, to improve your relationship (perhaps something to do with the way you resolve conflicts)?”

23. “When is the last time you felt let down?”

"When is the last time you felt let down?"-Shadow Work Prompts

24. “What in your life gives you the most purpose?”

25. “What things make you judgemental?”

26. “What emotions tend to bring out the worst in you?”

27. “What does freedom mean to you?”

28. “What would you most like to be recognised for?”

29. “Negative traits tend to develop in childhood as a defence mechanism. They’re useful at the time, but not as adults. List your least desirable traits. “

30. “What makes you feel most valued? “

31. “With whom or in which situations do you find yourself slipping on a mask or embodying a different persona?”

32. “Think about your friendships. Which ones make you feel safe, secure, and loved?”

33. “When have you been self-sabotaging or destructive in your life?”

34. “How do you tend to respond to compliments? Make a concerted effort to learn to simply say ‘thank you’, if you don’t already do this.”

Shadow Work Prompts For The Workplace

Work consumes an enormous amount of our time in life. Whether you work from home, go to an office, a school, a hospital, or a construction site, we all work.

Work is a place where we are evaluated and judged, not only by others but by ourselves as well.

Work is also the place where our greatest insecurities can emerge. We ask ourselves if we are good enough, can we do this particular task, do we have the skill and know-how, would a co-worker not be a better person for this task, and on and on.

We often sabotage our success at work because of self-doubt around our capabilities.

Work also provides an ideal stage for some of our nastier qualities to come to the fore. For example, you may really want that promotion, but others are also in the running. 

Your desire to win becomes so great that you become consumed with jealousy and hatred for your opponents.

Look at the list of prompts to help you work through issues you have that are associated with work.

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23 Shadow Work Prompts For Workplace

35. “What kind of work requests trigger you negatively? Why do you think that is?”

36. “How do people describe you at work?”

37. “What expectations feel hard to live up to at work?”

38. “What would you do differently if you could start your career over again?”

39. “Do you wish people treated you differently at work? How so?”

40. “What skill do you think you might have a knack for but don’t try or talk about because you’re afraid of failing?”

41. “What is something people often get wrong about you at work?”

42. “What kind of responsibilities drain you at work?”

43. “What do you wish you could change about your workplace or career?”

44. “What kind of advice do people come to you for? Why do you think that is?”

45. “What do you wish people knew about you at work?”

"What do you wish people knew about you at work?"

46. “What expectations feel easy to live up to but don’t feel authentic to who you are?”

47. “When was the last time you felt betrayed by someone? What happened? What do you wish they knew about you?”

48. “What does your family mean to you? How have they impacted your life?”

49. “What destructive patterns do you notice you repeat? Why do you think you repeat them?”

50. “What habits do you feel guilty or shameful about? Why?”

51. “If you found out you would die today, what would you regret not doing in your life?”

52. “What do you think others would think if the one thing you feel most shameful about were shared in every ad on YouTube?

53. “Who in your life takes up the most emotional energy? Why do you think that is?”

54. “What have you done that makes you feel most like a failure?”

55. “What is the meaning of success to you? Where do you think that comes from?”

56. “What kind of behaviors in others make you the angriest? Why? What does it say about you?”

57. “What do you have a hard time saying no to that you wish you could let go?”

Shadow Work Prompts For Relationships

In addition to work, the other major part of our lives is the relationships we have.

These relationships can include family, friends, and work colleagues.

If you find that your relationships never get beyond the surface, or you have issues with family members and you avoid spending time with them, or you feel that you always get taken advantage of by co-workers, it’s time to examine what is at the root of the problem.

It is important to remember that, in relationships, the only person we can control is ourselves. View this as empowering.

Read the list of relationship prompts and focus on the area which is the problem. 

This can take some real soul-searching, and may require you to pull out from the shadows, something that has happened in your past which has caused you to have this negative aspect of yourself.

This can be painful, but looking at it, writing about it, and dealing with it are how the healing begins.

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14 Shadow Work Prompts For Relationships

58. “What kind of relationships do you have with your parents/caregivers, siblings, or other close family members? Is it better, worse, or the same as when you were growing up? Why?”

59. “Who has the most influence over you? Do they know? Is it healthy?”

60. “Which relationships in your life no longer serve you. List them out. How would it feel to be free of these relationships? Why aren’t you?”

61. “Is there a person you can’t seem to forgive in your life? Write them a letter. What do you want to say to them?”

62. “Do you allow yourself to be vulnerable in relationships? Why or why not?”

63. “Have you ever been in a codependent relationship? What about your family members? Talk about your experience with codependency as well as thoughts or feelings that come up about it.”

64. “Do you struggle with commitment? What challenges have you faced in your dating life that you want to work on?”

65. “Think about a conflict you had with someone. How did it play out? Is there anything you wish you had done differently? What was your role in the conflict? Did you take responsibility?”

66. “In what ways are you similar to your parents/guardians? How are you different?”

67. “Write a letter to someone who has really hurt you. Let it all out. (Feel free to creatively destroy the letter when you’re done.)”

68. “Have you ever developed an obsessive or unhealthy relationship? Why do you think this happened?”

69. “What is your love language? How did you learn it?”

"What is your love language? How did you learn it?"-Shadow Work Prompts

70. “Is there anyone in your life who belittles you or downplays your emotions? How does that affect you?”

71. “Was there a time you opened yourself up to someone and felt rejected? What happened? How has that affected you?”

Forgiving And Healing Shadow Work Prompts

The key to moving on from hurt and despair is often forgiveness. We might feel angry toward someone who has wronged us in the past.

Left to sit and fester, this anger can increase which can have devastating effects on our relationships with people, and our general demeanor.

Once we can find it within ourselves to forgive that person, we can then heal.

Forgiveness may be something that you need to extend to yourself. We are often our own most critical judges, and when we don’t measure up to the expectations we have set for ourselves, we punish ourselves.

Recognizing that you are human, that you do not have to be perfect, and that accepting your faults is a positive thing can make you a much happier person. 

You will be less exacting of yourself and others. You will be able to find greater joy in life, and make time for relaxing and having fun.

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19 Forgiving & Healing Shadow Work Prompts

72. “Write about a time when you messed up and hurt someone. Did you apologize? Did you ask to be forgiven? How did the person react?”

73. “How do you react to criticism? Was there an element of truth in the criticism? Have you ever thanked someone for their criticism? Why or why not?”

74. “How did your emotions/feelings work against you this week? Which specific emotion(s) affected you? Do you usually take time to reflect and process these emotions at the end of the day?”

75. “What is the biggest lie you consistently tell yourself? How does it make you feel? How long have you been lying to yourself about this?”

76. “What tends to trigger envy for you? Why do you think this is?”

77. “Do you often find yourself overthinking what you’ve said or how you’ve acted? What usually triggers this?”

78. “How did you process negative emotions as a child and as a teenager? How do you process negative emotions now? What has changed over time?”

79. “When are you hardest on yourself? Why do you think that is? How has it affected you personally and professionally?”

80. “Write about one person who hurt you, but you have never forgiven. What happened? Why did you not forgive them? How has this event affected you going forward? Do you think you could forgive them now? How did you move on from this event?”

81. “Describe a time when someone broke a promise. How did it make you feel? Does it still bother you? If so, why?”

82. “List the areas in your life where you feel stuck or are not making progress. How long have you felt this way? What needs to happen for you to make progress?”

83. “What is the most hurtful thing that you have done to someone? Why did you do it? Does it still bother you? Have you asked that person for forgiveness? If not, why not?”

84. “What are your most significant areas of resistance? How long have you struggled in these areas? What triggers your resistance?”

85. “Who do you harbor resentment towards the most? Why do you resent them? How long have you felt this way? Write a short note as a first step to let go of the resentment.”

86. “How can you be kinder to myself? In what ways do you punish or sabotage myself?”

87. “What is the thing you feel most guilty about in your life to date?”

"What is the thing you feel most guilty about in your life to date?"

88. “Are there any behaviors that you were recently told were childish? How did it make you feel? Did you stop the behavior? Why or why not?”

89. “Would you say the things that that voice tells you to other people? If no, then those thoughts aren’t your true voice. They’re reflections of other people’s beliefs you’ve internalized.”

90. “Imagine your worst fear came true, how does that now make you feel about your life ahead?”

Shadow Journal Work Prompts For Authentic Life

Honesty is at the root of discovering aspects of our shadow self. In order to live an authentic life, to be present as our true and best selves, honesty is critical.

Feelings of shame, envy, jealousy, greed, anger, and pain keep us from living life to the fullest, and presenting to the world the person we truly want to be, without the shadow traits.

When we find the courage to face our shadow, we allow good to come and take its place.

We come out of the darkness, and are free to embrace life fully, with all of the marvelous opportunities that are available to us.

As challenging, and difficult as it is, dealing with the shadow aspects of ourselves allows us to explore all of our good traits and develop them through positive, gratifying relationships and experiences that fill our cup in a good way.

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22 Shadow Journal Work Prompts For Authentic Life

91. “What triggers jealousy in you? Why do you think that is?”

92. “When was the last time you felt disappointed? Does it make sense that you felt that way? Could something else have been triggering this feeling?”

93. “What makes you feel empty inside? When you feel this way, how do you try to fill the void? Are there healthier ways you could do this?”

94. “Do you value yourself and what you bring to the world?”

95. “What trait do you wish you had that you see in other people?”

96. “Who has the most influence over you? Are you okay with this influence?”

97. “Write down a time you felt betrayed. What would you say to that person now?”

98. “What are the first signs that your mental health is suffering?”

99. “What do you wish people understood about you? Is there a way you can better share that part of yourself with the world?”

100. “Are your core values similar to your parents or caregivers? Are you happy about that? Where else do you think your values came from?”

101. “Are you easily swayed by the opinions of others? Why or why not?”

102. “Imagine you are lying on your death bed. What regret do you fear having the most?”

103. “Do you frequently overthink what you’ve said or done? Why do you think that is?”

104. “Have you ever done something to make someone else proud? If so, who was that person and why did you care what they thought?”

105. “Do you think you’re only as good as your last achievement?”

106. “What would you change about the people closest to you? Is there something you could change in yourself to make these relationships stronger?”

107. “Have you ever sacrificed a part of who you are to fit in with others better? Why?”

108. “What does achievement mean to you? Do you celebrate your achievements?”

109. “How did it make you feel when you realized your parents weren’t perfect? Does it make it more accepting for you to not be perfect too?”

110. “In what areas of your life do you feel superior to your peers? Are you really?

111. “If you could be anything in the world, what would it be? Are you making steps toward being that person? Why or why not?”

112. “What traits do you see in yourself that remind you of your parents?”

"What traits do you see in yourself that remind you of your parents?"-Shadow Work Prompts

Frequently Asked Questions

Are These Prompts Suitable For Beginners In Shadow Work?

Yes, many shadow work prompts are suitable for beginners. They provide a gentle entry into the practice, allowing you to gradually delve into deeper aspects of your psyche as you become more comfortable with the process.

Can Shadow Work Prompts Be Used In Combination With Therapy Or Counseling?

Yes, shadow work prompts can complement therapy or counseling by providing additional tools for self-exploration. Discuss their use with your therapist or counselor to integrate them effectively into your healing process.

What Is The Goal Of Shadow Work?

The primary goal of shadow work is to integrate the hidden or suppressed aspects of your psyche into your conscious awareness. By doing so, you can achieve emotional healing, self-acceptance, and personal growth.

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