143 Shadow Work Prompts To Ease Yourself Into Transformation

Shadow work is the person we want to be challenging the person we are now.

Although shadow work can take place in many different forms, a great way to engage in this work is by using shadow work prompts.

With a pen and journal, you can uncover revelations about yourself that can lead to deep introspection.

Keep reading to learn what shadow work is and 143 prompts to lean into the unconscious.

What is Shadow Work for Beginners?

What does “shadow work” mean?

Shadow work can mean different things to different people. To put it simply, shadow work means working with yourself to uncover your unconscious thoughts, behaviors and experiences. This could mean reckoning with trauma or the parts of yourself you’d like to grow out of.

Examples of shadow work include:

• Contemplating your emotional reactions
• Working with a therapist through trauma
• Journaling to analyze your thoughts or emotions
• Meditating on your past to process your emotions

We call it “shadow work” because doing this work takes introspection and diving into the deeper layers of yourself. This isn’t surface-level stuff. It takes some real contemplation, honesty and vulnerability.

Shadow works relies on the concept of the “shadow self.” This phrase was developed by the late psychologist Carl Jung, a thought-leader of his time. In his definition, the shadow is the unconscious part of your personality that doesn’t match up to your ideal version of yourself. For example, maybe you’re typically a loving, caring and giving person. But your shadow shelf may reveal someone who gets defensive and angry when questioned.

Why Work on Shadow Work with Prompts?

The goal of shadow work is to bring the darker parts of you to light. In doing that, we can transform them to become happier, well-adjusted people.

For example, if we notice out troubled childhood is weighing us down, we can take steps to deal with those emotions and move past them.

As we know, ignoring a problem is a sure-fire way to make it stick around. Not dealing with your shadow self can lead to many problems, like:

• Depression
• Anxiety
• Anger
• Guilt
• Negative self-image
• Troubling relationships
• Lack of boundaries
• Poor behavior
• Poor judgment making

Although there’s many ways to do this work, shadow work prompts provide an easy gateway. All you need in your mind, paper and a pen.

A Note on Shadow Work and Psychotherapy

Shadow work is a narrow term for something that can encompass a lot. Shadow work can mean dealing with trauma, such as experiences of childhood abuse, domestic violence, sexual violence and more. These are experiences that are best addressed by a healthcare professional, such as a counselor, therapist and psychotherapist. While shadow work can be a spiritual term, sometimes it requires science-backed advice. Please always seek out evidence-based resources for emotional trauma before taking a DIY approach.

Opening up emotional wounds can make you feel worse if you don’t have the appropriate skills to cope. This can deepen trauma and exacerbate any mental health symptoms you may be experiencing. Please always consider getting the help of a trusted professional before delving into shadow work. And please know that you never have to do it alone.

If you can’t afford therapy, you can ask local community centers for free or low-cost resources. Some therapists also work on a sliding scale, adjusting their rates to your income. You can also join peer support mental health groups on Facebook or other platforms.

What are Shadow Work Prompts?

Shadow work prompts are questions or statements to encourage deeper thought. Typically, people choose a statement and write an entry in their journal about it. While writing, focus on the thoughts, opinions and behaviors the prompt might elicit.

The most important part of shadow work prompts is to be honest with yourself. If you can’t look at yourself honesty, you can’t get to the deeper levels where shadow work takes place. Which also means that you can’t transform the parts of you that need overcoming. Some things that come up will make you uncomfortable. That’s a normal part of shadow work. As you evaluate the things about yourself that need healing, you might feel worse about yourself—which leads us to our second point…

Use Self-Compassion When Using Shadow Work Prompts

Another critical part of shadow work is self-compassion. Looking at yourself honesty can lead to feelings of guilt or even worthlessness and lower confidence. For example, you might recognize that you sometimes treat people with judgment or hostility. Although true, this can make you feel horrible about yourself. Please know this is not the point of shadow work! When you uncover uncomfortable truths, take a moment to practice self-compassion. Here’s a few quick tips on that:

• Recognize that no one is perfect—including you
• Recognize that everyone makes mistakes—including you
• Recognize that you’re doing your best at any given time. And now that you know better, you can do better. Everyone learns and grows.
• Talk to yourself as you would a friend (kindly and non-judgementally)
• Try guided self-compassion exercises
• Listen to 11 Self-Compassion Meditations To Change Your Life

143 Shadow Work Prompts

You can work through these shadow work prompts one by one, choosing one a day. Or you may select those that are the most appealing to you. Another idea: Choose the shadow work prompts that are the most unappealing. They might lead to the most revelation and change.

1. What do you hope to gain from shadow work prompts?
2. What triggers you? What do you think caused those triggers?
3. On a scale from 1 to 10, how happy are you? What would contribute to your happiness?
4. What are you most critical of yourself for?
5. What traits do you dislike in yourself?
6. In which ways are you too hard on yourself?
7. What’s the most harmful thing you’ve ever done?
8. Do you enjoy where you’re living?
9. Are your environments feeding your happiness or unhappiness?
10. How do you feel about the people in your life?
11. Describe your relationship with your family members.
12. What are your biggest fears?
13. Do you love yourself? Why or why not?
14. Do you have any resentment toward anyone in your life?
15. Who gave you the most love growing up?
16. What traits in your parents do you see in yourself?
17. What would have improved your childhood?
18. What are your biggest memories from childhood?
19. What are your biggest memories from your teenage years?
20. What are your biggest memories from your 20s?
21. What are you least confident about in yourself?
22. If you could change anything about yourself, what would it be?
23. What traits do you dislike most in other people?
24. What recent conversations do you think you could have handled better?
25. What recent conflicts do you think you could have handled better?
26. In which ways do you inflame conflicts?
27. Do you usually escalate or deescalate conflicts?
28. Are there any common themes in your conflicts?
29. How do you think you can better connect with others?
30. What harsh words do you wish you could take back?
31. What actions do you wish you could take back?
32. What are the biggest lessons you’ve learned to date?
33. Which emotions do you avoid feeling?
34. When you’re down, what actions or thoughts make you feel worse?
35. Do you allow yourself to be vulnerable when it’s safe?
36. What are people’s biggest criticisms about you?
37. What are your boundaries?
38. Do you enforce your boundaries?
39. How can you better enforce your boundaries?
40. Do other people tend to cross your boundaries? How?
41. What is holding you back from enforcing boundaries?
42. Does everyone in your life belong in it?
43. Do you have a different personality in public vs. private? How?
44. Are you confident standing up for yourself?
45. Are there any traumatic situations that shaped you as a person?
46. List a few of the worst pieces of advice you’ve received. Why are they the worst?
47. What piece of advice did you accept only to figure out it’s bad advice?
48. What piece of spiritual advice or knowledge do you disagree with?
49. Which of your actions or behaviors contribute to toxic relationships?
50. How do you receive constructive criticism?
51. Who are you consciously or unconsciously in competition with?
52. Is there anyone who makes you envious?
53. Is there an event in your life that you feel you can’t get over?
54. Is there a person in your life that you feel you can’t get over?
55. Which habits contribute to your well-being?
56. Which habits impede your well-being?
57. Do you have any addictive tendencies?
58. What’s the biggest lie you ever told?
59. How can you better support the people in your life?
60. How can the people in your life better support you?
61. How do you handle compliments?
62. Which compliments have meant the most to you and why?
63. Which insults have hurt you the most and why?
64. What’s the most hurtful thing someone has done to you?
65. In what ways have you internalized misogyny?
66. In what ways do you contribute to misogyny?
67. In what ways do you contribute to racism?
68. When have you stood down when you could have stood up for something or someone else?
69. What has been the hardest thing you’ve had to unlearn?
70. How do you think people perceive you?
71. How do you want people to perceive you?
72. Who or what sets off your inner “judge Judy”? Why?
73. In which ways can you be less judgemental toward others?
74. In which ways can you be less judgemental toward yourself?
75. What are the biggest misconceptions about you?
76. How do you self-soothe?
77. Do you have trouble saying sorry? Why or why not?
78. Who’s the last person you said sorry to? What about?
79. Who’s the last person who apologized to you? What about?
80. Do you feel anyone still owes you an apology? Describe.
81. What did you last cry about?
82. What are your core values?
83. When are you out of alignment with your core values?
84. Are you living out your life’s “purpose”? Why or why not?
85. What do you dislike most about life?
86. How do the people in your life influence you?
87. In which ways might you be taken advantage of?
88. In which ways might you take advantage of other people?
89. What makes you feel unloved?
90. Are you more passive or dominant? Is there anything you should change about that?
91. Do you feel inferior or more important than others?
92. What makes you feel ashamed about yourself?
93. Is there anything you feel guilty about?
94. What does success look like to you?
95. How have you dealt with recent failures? Can you deal with them better?
96. Are your coping mechanisms working? Should you try something new?
97. In which areas of your life are you afraid to ask for help?
98. What do you avoid telling people about your life? Why?
99. Is there anyone you avoid seeing or speaking to? Why?
100. Are there any ways you self-sabotage?
101. Which talents do you wish you were better at?
102. Who makes you feel at home?
103. Who makes you feel safe?
104. Who makes you feel unsafe?
105. What are your most memorable nightmares? What do you think they mean?
106. Which area of your life are you struggling in?
107. Do you find it more difficult to be alone or with others? Why?
108. Are you good at thinking before speaking?
109. In which areas of life can you be more gentle with yourself?
110. In which areas of life can you be more gentle with others?
111. What should you spend more time doing?
112. What should you spend less time doing?
113. What actions would contribute to better health?
114. What actions would contribute to better mental health?
115. What’s your biggest regret? (If you don’t have regrets, what’s the biggest “mistake” you’d redo differently a second time around?)
116. If you died today, what would you regret most?
117. If you died today, what would you be most proud of?
118. How do you want people to remember you after you’ve passed?
119. If you passed today, what do you think people would say at your funeral?
120. How can you be at peace with your regrets?
121. Who has been the hardest to forgive?
122. Is there anyone you feel you shouldn’t forgive?
123. In what ways do you let yourself down?
124. In what ways do you feel you let others down?
125. Who lets you down and why?
126. When do you feel most depressed?
127. When do you feel most anxious?
128. When do you feel happiest?
129. What are you least proud of in yourself?
130. Which parts of yourself do you hide from others?
131. Which parts of yourself do you hide from yourself?
132. Does anyone in your life dim your light?
133. In which ways do you dim your own light?
134. What does power mean to you?
135. Describe your relationship with power.
136. Has anyone in your life abused their power?
137. When do you feel most powerful?
138. Have you ever abused your power?
139. Who makes you feel the most valued?
140. Who makes you feel the least valued?
141. What makes you feel most angry? Why?
142. What injustices tick you off the most? Why?
143. Is there anything you’re running away from or not facing?

Summary: Shadow Work Prompts

Shadow work prompts can help you discover hidden truths about yourself. This can deepen your knowledge about yourself and provide the introspection needed for positive change. Remember that shadow work can take many forms, not just journaling with shadow work prompts. Sometimes our journey requires professional help, such as that of a mental health professional. Therapists and counselors can help us work through our shadow side in an environment that’s safe. They can give us the tools needed to overcome challenges and deal with the difficult emotions shadow work can bring up.