Shadow work prompts are ideal for getting started with shadow work. Shadow journaling is one of the very best ways to begin and this post offers a list of 50 intense prompts for self-reflection and healing.

Everything You Need to Know About Shadow Work Prompts For Healing

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

If you’ve not come across the term ‘shadow work’ before then here’s a little more about what you need to know before getting started with shadow work questions and prompts…

We All Have a Shadow

Our shadow, a term coined by psychologist Carl Jung, is the part of ourselves which we hide – or may not even be aware of. We either reject and/or repress those aspects of our personalities which we find unsavoury, and if we don’t immediately know the traits in ourselves for which this applies, then chances are they are indeed being repressed.

Read: 400+ Journal Prompts to Inspire and Motivate you!

But that’s okay – nobody is immune. And by being here and reading about it you’re taking the first step towards doing something positive and proactive about it.

Our shadows develop primitively and instinctively as a survival mechanism, so while they may not contain attractive qualities, they’re largely beyond our control and have served a vital purpose at some time. But the fact is, they can remain hidden deep within us long beyond when they stopped serving us, and this is actually a clue to identifying our own particular shadow traits:

One way in which the characteristics of our shadows show up in our lives is as self-sabotage.

And let’s face it – who wouldn’t want to challenge the part of themselves that’s responsible for ruining the good in their lives? It’s a complex and uncomfortable process, but ultimately so worthwhile.

Woman Saluting Sky - Freedom

Head over to my other post to learn more about shadow work, how it can negatively influence your life – as well as the many benefits of actively facing your shadow self.

How Do You Face Your Shadow Self?

Facing your shadow self is as simple and excruciating as acknowledging and challenging your least attractive qualities.

Challenging our shadows is a daunting task, because it essentially means looking right into the heart of the most shameful and vulnerable parts of ourselves. But, whether we like it or not, just because we refuse to acknowledge those unattractive traits at the core of who we are, does not mean they don’t exist. What is does mean is that they hold power over us.

The first step towards healing is to understand that – just as with undesirable behaviour in children – our least glamorous qualities are or were the result of an unmet need. The next step is to acknowledge that we’re now in a position to meet that need for ourselves, if it has not already been met as we’ve grown and matured.

Then it’s up to the present, adult, rational version of ourselves to identify, acknowledge, and communicate with the primitive shadow self; to bring it out into the light and show self-compassion to our younger, fallible self.

How Do You Practice Shadow Work?

The gold standard for intense shadow healing is through journaling. Using shadow work prompts can help with this process.

A wellbeing journal like this one is ideal for answering shadow work questions and prompts, to help you make peace with your shadow.

The below 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 prove.

How Shadow Work Prompts & Exercises Can Help Restore Harmony

When it comes to shadow work, 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. I’m sharing some of my favourite shadow work journal prompts below to help you bring your shadow parts into the light.

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.

What Are Some Good Shadow Work Prompts to Help You Heal and Grow?

Good shadow work journal prompts are any that make you squirm and cringe – they may be difficult to work through, but you can bet they’re also very effective at their purpose. To get the most value from your shadow work prompts, you’ll have to challenge yourself.

Each of those below are designed for exactly this purpose, with the eventual goal of helping you to heal and grow.

Taking yourself through this uncomfortable process will help you to accomplish your goal of finding a greater sense of calm and peace.

Shadow work journaling prompts pin

50 Challenging Shadow Work Journal Prompts to Bring You Peace

For all of the reasons outlined above, journaling is my preferred method of shadow work. Here are some excellent shadow work journaling prompts for you to work on:

  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. Do you have or have you had recurring nightmares? What’s the theme? What might it relate to? How might you face the fear causing your nightmare?
  23. What’s the worst thing you’ve ever done? What drove you to it? Have you confessed to your misdemeanor? Are you afraid of being honest? Examine why this is and whether it’s truly valid. Are you protecting yourself or others? Could being open about it help to bring you peace? How might you atone for it?
  24. What authority figures (individuals as opposed to institutions) did you respect growing up? What qualities did/do they possess? Do you share those traits? How might you develop/enhance them?
  25. How are you letting yourself down at this time in your life? How could you be better to yourself? Consider your health, finances, relationships, work, etc.
  26. What lies have you previously told yourself? Are you being entirely truthful with yourself at this time in your life?
  27. What was your last uncharitable thought? Did you voice it? Was it deserved? Were you being unfairly judgemental?
  28. Who has let you down the most in your life? Are they still around? How do you feel about that?
  29. 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.
  30. 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?
  31. 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?
  32. Do you have any other traumatic childhood memories?
  33. 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?
  34. What are your parents’ best/worst attributes? How are you alike/unlike them? 
  35. 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?
  36. 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?
  37. How does drama make you feel? Are you dramatic yourself? Do people call you dramatic? How do you feel about this?
  38. Who do you hold a grudge against? What is stopping you from letting it go?
  39. 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?
  40. How do you view asking for help? Is it a sign of strength or weakness? Why is this?
  41. What makes you self-conscious around others?
  42. What makes you feel unsafe? Explore this.
  43. What could have made your childhood better? How do you feel about that?
  44. 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?
  45. 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.
  46. What does freedom mean to you?
  47. What in your life gives you the most purpose? 
  48. 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?
  49. What makes you feel most valued? 
  50. What would you most like to be recognised for?

The Benefit of Shadow Work Questions

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. 


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