If you’re ready to get started with shadow working, then journaling is one of the very best ways to begin. Journaling is an excellent technique because it can be combined with other shadow work exercises, but also brings the benefit of a written record. Writing is powerful in itself, and having something to refer back to means you’re able to track your progress too. Today I’m sharing some of my favourite shadow work prompts to help you bring your shadow parts into the light.

Shadow Work Journal Prompts to Help You Heal and Grow

I’m a huge advocate of journaling, and shadow work is the ultimate and most valuable form: it’s the hardest to participate in, but also promises the greatest reward.

These shadow work prompts are designed to get you to really dig deep. They’re not intended to be comfortable, and may well be quite challenging; they’re meant to be. The more probing and difficult the questions you ask yourself, the more beneficial the process of answering them will be.

shadow work pin

Challenging Shadow Work Prompts to Bring You Peace

  1. What do you think are the worst character traits a person can have? When is a time you have demonstrated these traits?
  2. How do you think people see you? How would they describe you? How do you feel about that?
  3. What things are triggers for you? Consider where those irrational feelings stem from.
  4. What things make you judgemental? Think about a hypothetical situation in which you’d agree somebody could behave in a way you’d usually judge, yet be entirely innocent.
  5. When is the last time you felt let down? Examine how you felt and whether it was truly rational, or if you were triggered.
  6. Who has the most influence over you? Is that healthy?
  7. Who do you envy? Why? How might you be able to work towards gaining the things they have that you feel jealousy towards?
  8. Think of a relationship you’ve walked away from. Write down the reasons it’s been a positive life choice.
  9. What person has hurt you the most in your life? Write them a letter telling them all the things you’d like to say.
  10. What most frightens you? How might you be able to expose yourself to that fear in a safe way?
  11. What misconception do people have about you? How does that make you feel?
  12. What memories bring you shame? Think about who you were then, what led to your behaviour, and how you’ve changed since. Now write out the words ‘I did the best I could at the time and I forgive myself’.
  13. 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. 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.  
  14. Which traits would you least wish to be described as having? Why would it be so terrible?
  15. Who or when last/regularly belittles or downplays your emotions? How does it make you feel?
  16. What emotions tend to bring out the worst in you? Why do you think that is?
  17. When have you been self-sabotaging or destructive in your life? Examine how you were feeling at the time, and what triggered your behaviour.
  18. Think about your friendships. Which ones make you feel safe, secure, and loved? Do you have any in which you feel isolated, pressured, or otherwise uncomfortable? Examine why this may be and if you have any negative history.
  19. Which relationships in your life no longer serve you? Be ruthless – nobody else will see this. 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. perhaps write a letter to that person/those people.
  20. What do you most dislike about yourself? Really examine why that is, and whether you’d feel the same level of distaste for somebody else in your position.
  21. What do you wish people understood about you? How might you be better able to demonstrate the quality that people tend to overlook?
  22. What was your last uncharitable thought? Did you voice it? Was it deserved? Were you being unfairly judgemental?
  23. Who has let you down the most in your life? Are they still around? How do you feel about that?
  24. What’s your biggest regret in life? 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.
  25. What’s your worst childhood memory? Who was there? How did they comfort you or make it worse? What would you like to say to them?
  26. What situation in your life do you most wish had had a different outcome? How would it have improved your life? In what ways is your life better for it not having worked out?
  27. Do you have any other traumatic childhood memories?
  28. What’s the worst character trait you have as a result of your childhood? What or who do you think caused it? how do you feel about that?
  29. What are your parents’ best/worst attributes? How are you alike/unalike them? 
  30. What is the worst emotion somebody could provoke in you? For example, anger, betrayal, jealousy. Why do you feel so strongly about this? Does your answer differ according to the person in question?
  31. How do you feel about your childhood? Was it generally positive or negative? Who made you feel safe and who let you down? Who were you close to?
  32. How does drama make you feel? Are you dramatic yourself? Do people call you dramatic? How do you feel about this?
  33. Who do you hold a grudge against? What is stopping you from letting it go?
  34. Who have you previously had conflict with and allegedly resolved it, but you remain wary of since? How did they make you feel? What worries you about the relationship now?
  35. How do you view asking for help? Is it a sign of strength or weakness? Why is this?
  36. What makes you self-conscious around others?
  37. What makes you feel unsafe? Explore this.
  38. What could have made your childhood better? How do you feel about that?
  39. What one thing could somebody say to you to bring you to your knees? Why do those words hold so much power? How can you begin to take the power out of those words?
  40. Who have you most let down in your lifetime, and how/why did it happen? Have you made peace with the situation? Write a letter to the person you disappointed telling them how you feel, even if you don’t send it.
  41. What does freedom mean to you?
  42. What in your life gives you the most purpose? 
  43. 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)? How does that reflect on you? Based on this exercise, is there anything you could consider improving in yourself to help?
  44. What makes you feel most valued? 
  45. What would you most like to be recognised for?
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The Benefit of Shadow Work Exercises

Working your way through these prompts – and perhaps revisiting some of them regularly – is a wonderful way to identify your weaknesses, and work on them with compassion.

Shadow work journal prompts. Image shows a woman writing in a diary.

They may also help you to recognise painful truths about relationships which you’ve repressed or denied. And, crucially, to consider what you learn from a non-judgemental perspective. We can’t control others, we can only control ourselves, and this is the foundation of shadow work:

Awareness and acceptance of our faults and limitations, forgiving ourselves and others, and letting go of the pain we’re holding onto in order to live a more peaceful life. 


Journaling, Positivity

An award-nominated blogger and author, Kate is a huge advocate of personal growth, focusing on journaling to increase positivity and facilitate mindful motherhood. With a wealth of experience in breastfeeding and CMPA, Kate is also an expert baby sleep chaser. Her writing has appeared on Mothercare, Huff Post, and BritMums.

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