15 Shadow Work Questions & Prompts

1. How do you think people see you?

i) How would they describe you?
ii) How do you feel about that?

2. 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?

3. What things make you judgemental?

i) Think about a hypothetical situation in which you’d agree somebody could behave in a way you’d
usually judge, yet be entirely innocent.

4. When is the last time you felt let down?

i) Examine how you felt and whether it was truly rational, or if you were triggered.

5. Do you have healthy boundaries in your relationships?

i) Is there any particular relationship that you feel could benefit from stronger boundaries?
ii) Explore what is preventing you from having the courage to hold that space.
iii) Can you say with complete honesty that you respect the boundaries of others?

6. List out your core values.

i) Are you living in alignment with them? What could you change to be more in harmony with them?
ii) Do they match those of your childhood caregivers?
iii) If not, explore why this might be.

7. What do you wish people understood about you?

i) How might you be better able to demonstrate the quality that people tend to overlook?

8. What makes you feel empty? How do you tend to fill that void?
i) What are some healthy strategies you might develop to overcome feelings of emptiness?

9. Who has the most influence over you?

i) Is that healthy?

10. Who do you envy?

i) Why?
ii) How might you be able to work towards gaining the things they have that you feel jealousy towards?

11. What does freedom mean to you?

12. What in your life gives you the most purpose?

13. 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)?
i) How does that reflect on you?
ii) Based on this exercise, is there anything you could consider improving in yourself to help?
 14. What makes you feel most valued?

15. What would you most like to be recognised for?

60 More Challenging Shadow Work Prompts For Journaling

Here are some powerful shadow work journaling prompts for you to work on:

16. Do you consider yourself to be confrontational? Why? Is this something you’re proud of or would you
prefer to be different?
i) Would others be more likely to describe you as confrontational or a pushover? How would you prefer
to be viewed?

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

18. Describe yourself with objectivity.

i) How easy was this task? Do you know who you truly are?
ii) Do you like who you are?

19. What person has hurt you the most in your life?
i) Write them a letter telling them all the things you’d like to say.

20. What most frightens you?

i) How might you be able to expose yourself to that fear in a safe way?

21. What misconception do people have about you?

i) How does that make you feel?

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

23. What memories bring you shame?

i) Think about who you were then, what led to your behaviour, and how you’ve changed since.
ii) Now write out the words ‘I did the best I could at the time and I forgive myself’.

24. 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.
i) Consider your past self as you would perhaps a younger sibling, from a position of honesty and
compassion. Write your past self a letter, demonstrating understanding and forgiveness.

25. Which traits would you least wish to be described as having?

i) Why would it be so terrible?

26. Do you similar trait or traits do you share with your parents or childhood caregivers?
i) Is this a conscious decision? In what ways would you like to emulate them?
ii) How do you actively choose (or try) to be different?
27. What is your definition of failure?
i) What makes these circumstances so terrible?
ii) Imagine yourself in this situation. Write down five things you believe people would think about you.
iii) Now write down five things you would hope people would think of you.

28. Who regularly (or last) belittles or downplays your emotions?

i) How does it make you feel?

29. Think about unhealthy relationships you have currently or have had previously. What’s the common
theme?
i) Why do you think you find yourself in this kind of dynamic?
ii) How can you recognise and avoid allowing this type of relationship to develop?

30. What emotions tend to bring out the worst in you?

i) Why do you think that is?

31. When have you been self-sabotaging or destructive in your life?

i) Examine how you were feeling at the time, and what triggered your behaviour.

32. With whom or in which situations do you find yourself slipping on a mask or embodying a different
persona?
i) What do you think would happen if you exposed your true self?
ii) How does that make you feel?
33. 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.
i) Where do they come from?
i) Think about their purpose, and write about more positive and productive behaviours you could use
instead.
iii) Think about others you know who display these traits too, and how they make you feel. Make a
promise to yourself to remember to look past the trait to the vulnerability behind it in future – we do not
know other people’s stories.

34. Think about your friendships. Which ones make you feel safe, secure, and loved?
i) Do you have any in which you feel isolated, pressured, or otherwise uncomfortable?
ii) Examine why this may be and if you have any negative history.

35. 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.

36. Which relationships in your life no longer serve you? Be ruthless – nobody else will see this.
i) Which relationships feel obligatory or dutiful. Consider how you’d feel if you allowed those
relationships to dissolve, then think about whether they’re worth trying to salvage, and how you may be
able to do that.
ii) Perhaps write a letter to that person/those people.
37. What do you most dislike about yourself?
i) Really examine why that is, and whether you’d feel the same level of distaste for somebody else in
your position.

38. What do you think are the worst traits a person can have?
i) When is a time you have demonstrated these traits?

39. What things are triggers for you?

i) Consider where those irrational and negative feelings stem from.

40. Do you have or have you had recurring nightmares? What’s the theme? What might it relate to?
i) How might you face the fear causing your nightmare?

41. What’s the worst way you’ve been taken advantage of in your lifetime?
i) Think about the person who treated you that way, and consider their circumstances. What do you
think drove them to it?
ii) If you don’t know enough about them to answer this question, imagine what their story is. Write it
down, keeping in mind that nobody is born evil. Terrible life experiences do not excuse terrible
behaviours unto others, but they can help you to forgive and make peace.

42. Now imagine somebody else is working through the previous exercise and they are picturing you.
i) Who is the person, and what did you do to them?
ii) What were your circumstances at the time? Write a letter to the person explaining yourself and
apologising.
iii) Have you forgiven yourself? Imagine the person writing their letter to you, and then forgiving you.
Take a deep breath, and as you exhale breathe out any feelings of guilt you’ve been holding onto.

43. What’s the worst thing you’ve ever done?

i) What drove you to it?
ii) Have you confessed to your misdemeanour? Are you afraid of being honest?
iii) Examine why this is and whether it’s truly valid.
iv) Are you protecting yourself or others?
v) Could being open about it help to bring you peace?
vi) How might you atone for it?

44. What authority figures (individuals as opposed to institutions) did you respect growing up?
i) What qualities did/do they possess?
ii) Do you share those traits? How might you develop/enhance them?

45. Without thinking too deeply, what’s your gut reaction to the question ‘Do people respect you’?
i) Why do you think this is?
ii) How do you feel about this?

46. How are you letting yourself down at this time in your life?
i) How could you be better to yourself? Consider your health, finances, relationships, work, etc.

47. What is the biggest lie you tell yourself?

i) Are you being entirely truthful with yourself at this time in your life?

48. When you are alone, what does the voice of your inner self sound like? Is it positive or negative?
i) Consider whose voice that truly is.
 ii) Write a letter to the person who became your inner voice, thanking them if they champion you, or
challenging them if they are critical.

49. What was your last uncharitable thought? Did you voice it?
i) Was it deserved?
ii) Were you being unfairly judgemental?

50. Who do you owe an apology to? Make a list of everyone you can think of, even if it’s from a different
time in your life.
i) If anybody springs to mind, write them a letter. You don’t have to send it if it’s not appropriate to do
so, but write it anyway.

51. Who owes you an apology?

i) Why? What did they do? Is it possible you misinterpreted the situation?
ii) Write yourself a letter from their perspective, explaining the reasons for their transgression, and
apologising.
iii) Now take a deep breath, and as you exhale breathe out any resentment or hurtful thing you’ve been
holding onto.

52. What’s your biggest regret in life?

i) How might you be able to make peace with that? Think about your circumstances at the time and give
yourself permission to be okay with the fact that you did your best at the time.

53. What’s your worst childhood memory?

i) Who was there?
ii) How did they comfort you or make it worse?
iii) What would you like to say to them? Perhaps write them an unsent letter.

54. Do you have any other traumatic childhood memories?

55. What situation in your life do you most wish had had a different outcome?
i) How would it have improved your life?
ii) In what ways is your life better for it not having worked out?

56. Who do you feel inferior to?

i) Objectively explore whether they have intentionally made you feel this way, or if it’s your own
feelings of inadequacy creating that illusion.
ii) How do you think they view you or feel about you? Why?

57. Who has let you down the most in your life?
i) Are they still around? How do you feel about that?

58. What’s the worst character trait you have as a result of your childhood?
i) What or who do you think caused it?
ii) How do you feel about that?

59. What are your parents’ best/worst attributes?

i) How are you alike/unlike them?
60. What is the worst emotion somebody could provoke in you? For example, anger, betrayal, jealousy.
i) Why do you feel so strongly about this?
ii) Does your answer differ according to the person in question?

61. Think about a time you were manipulative. Explore the feeling behind the behaviour – what need made
you behave that way? Have you overcome that feeling?

62. How do you feel about your childhood?

i) Was it generally positive or negative?
ii) Who made you feel safe and who let you down?
iii) Who were you close to?

63. How does drama make you feel?

i) Are you dramatic yourself?
ii) Do people call you dramatic? How do you feel about this?

64. Which of your traits do you find it difficult to accept? Explore why this is.
i) Do you accept these traits in others? Do others readily accept these traits?
ii) Think of somebody who shares this characteristic with you. Write down three things you admire
about them.
iii) This trait does not define you; write down three different ways that you are more than this
characteristic.

65. Who do you hold a grudge against?

i) What is stopping you from letting it go?

66. Think about a time you felt betrayed. Have you made peace with the person involved? Write them a
letter explaining how it made you feel, and forgiving them.
67. Thinking about the previous exercise; now consider when you may have behaved similarly. Has the
person involved treated you as though you betrayed them? Either way, write them a letter apologising.

68. Who have you previously had conflict with and allegedly resolved it, but you remain wary of since?
i) How did they make you feel?
ii) What worries you about the relationship now?

69. How do you view asking for help?

i) Is it a sign of strength or weakness? Why is this?

70. What makes you self-conscious around others?

71. Who dislikes you or treats you poorly or with disrespect?

i) How does it make you feel?
ii) Where does this attitude or behaviour come from?
iii) Being very honest, is it deserved? Do you owe this person an apology?
iv) If you do, write them a letter apologising sincerely, or reach out in some other way.
v) Write this sentence down ten times: Other people’s opinions of me are none of my business.

72. What makes you feel unsafe? Explore this.

73. What could have made your childhood better? How do you feel about that?

74. What one thing could somebody say to you to bring you to your knees?
i) Why do those words hold so much power?
ii) How can you begin to take the power out of those words?

75. Who have you most let down in your lifetime, and how/why did it happen?
i) Have you made peace with the situation?
ii) Write a letter to the person you disappointed telling them how you feel, even if you don’t send it.