Do you feel as though there are deeper layers of yourself that are just waiting to be unearthed? Do you have a deeper desire to know more about who you are – who you really are – at a core and soul level? Do you sometimes wonder why you think, act and feel the way you do and have a yearning to understand what it is that triggers those exact choices, decisions and thoughts?

These are undeniably complex but interesting questions that appear when we have a deep desire to address the unconscious, deeply buried aspect of our personality. Aka the shadow self.

In this guide, we’ll embark on the journey to meet our shadow self through deep shadow work prompts and questions. Then, we’ll discuss what we can do with the shadow side of ourselves so that it has a positive and real world impact in our lives. 

Word of warning, shadow work isn’t to be taken lightly. It can trigger unhealed trauma, challenging and complex thoughts as well as existential crises in some people.

That said, it’s also a life changing technique and tool that can be used for intense healing, growth and self discovery. 

As a psychotherapist in training, you’re in good hands, but I feel it’s my duty to give you fair warning before proceeding. The shadow work prompts are designed to become progressively more ‘heavy-duty’ as you work down the list, though all are fairly challenging.

If at any point you feel it’s become too much – stop, process what you’ve already uncovered and then return when you feel emotionally equipped and stable to do so.

Let’s get started.


There are a LOT of layers to the shadow self, but in simple terms, the shadow self is everything that is not fully integrated with the conscious aspect of our ego or reality.

It houses everything you repressed and ‘brushed off’ during your childhood and early adulthood as a form of psychological protection in order to fit in, be loved or be accepted.

In other words, you can view the shadow side of yourself as the irrational, wounded, instinctive child-like part of your personality, the part of you that can harbor anything from intense rage to profound inferiority. 

In some way, your shadow self is like a wild animal in that it represents that side of us that we choose not to ‘let loose’ in society for fear of abandonment, judgement or criticism. 

Here’s where it gets interesting though. The shadow self is neither negative nor positive, though you may have read that the shadow self carries inherently negative traits (which kind of is AND isn’t true).

In some people, the shadow self is largely made up of repressed, rejected and least desirable qualities of themselves which is why it often gets a bad rap.

In others (especially those suffering from low self esteem, low self confidence, impostor syndrome etc), the shadow side is a powerhouse of false beliefs internalized from past experiences and traumas that continues to dominate their waking life.

In either case, confronting the shadow self face to face gives us an opportunity to identify and heal faulty beliefs, the wounded inner child and have many breakthrough moments that allow us to make progress in all areas of our life. 


Shadow work is the intensely personal, but deeply gratifying process of journeying within to meet the darkest, most repressed side of yourself. It requires compassion, kindness, patience and a need to let go of any assumptions or expectations – not to mention letting go of always being in control.

Shadow work doesn’t work when you’re actively trying to hide and deny the feelings and thoughts that bubble up. You absolutely need to be comfortable with confronting the weirdest, most illogical, most terrifying, irrational parts of yourself – the parts of you that feel wounded and sad.

The parts of you that feel anguish and despair.

The parts of you that acknowledge you were treated unfairly and so want to scream about the injustice in the world.

The parts of you that feel as though you’re living a life of ‘fakeness’.

Shadow work attempts to dig deep to understand what thoughts, feelings, memories and emotional processes were buried in an attempt to protect and preserve the conscious part of your reality.  Anything that makes you feel uneasy or uncomfortable is likely a good place to start. 

Fun fact: you can’t heal what you aren’t aware of.


Before you dive deep into these prompts, I want you to practice and uphold a self care practice. You might think you’re fully capable of handling what arises from a ‘few simple questions’, but before you know it, your answer has affected you all day and you can’t stop thinking about it.

These moments will happen – it’s normal.

It’s also normal to feel a sense of detachment with the world and those around you for a little while, at least until you’ve processed what came up for you. Give yourself some space to breathe.

Shadow work will never be complete, it’s something that follows you (just like your shadow) on the journey that is life. It can wait until you’re ready to pick it up again.


  1. Which emotion makes me feel the most uneasy or uncomfortable to sit with? Which one do I try to avoid the most?
  2. Think back to a scenario or situation where that emotion played out. What happened? How did I react initially? What other emotions played out alongside the one I tried to avoid?
  3. What negative emotions am I most comfortable with? Do I cling to certain emotions on a day to day basis because they feel ‘normal’?
  4. Is your inner voice kind or critical? What things does it say to you on a typical day?
  5. Is your inner voice truly yours? Who’s voice could be influencing your inner voice? (Parents, partners, teachers, friends etc). 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.
  6. ‘I am easily influenced or swayed by the opinions and beliefs of others. I find it hard to assert my own voice and figure out what is them versus me’. Explore this statement.
  7. ‘I regularly downplay how I feel or what I’m really thinking for the sake of others’. Do you agree or disagree with this statement?
  8. Looking at your past, who has or still does regularly downplay how you feel?
  9. Why do you let people who don’t acknowledge your feelings stay in your life? Do you have a desire to keep their company? Or, do you know that there’s something you could be doing too to make the relationship better?
  10. Do I value myself and what I bring to the table?
  11. How can I be kinder to myself? In what ways do I punish or sabotage myself?
  12. How important am I to myself? 
  13. Have you ever done something just to make someone else feel proud of you? If so, who was it and why?
  14. Do you fully celebrate your achievements? Or, is there a disconnect between your achievements and who you are as a person? Which one resonates more?
  15. What is your biggest regret to date?
  16. Imagine you’re coming to the end of your life, what is the biggest regret you fear having the most? How does that make you feel and where does it sit within the body?
  17. Imagine your worst fear came true, how does that now make you feel about your life ahead?
  18. Imagine your most wanted dream came true right now, how does that make you feel about your life ahead? Are there similar feelings and emotions tied to both your fears and successes?
  19. Do you feel you’re only as ‘good as your last achievement’? If yes, why? If no, why not?
  20. What do you think are your most undesirable traits and characteristics? (This is NOT an opportunity to put yourself down but rather a chance to unearth what you believe to be true about yourself. This doesn’t mean what you write is an accurate reflection of yourself).
  21. What image do you think other people carry about you?
  22. How would you like others to describe you? Is there a difference between your answer to this question and the previous one? How does that make you feel?
  23. ‘If I could be anything in the world, I would be …..’ fill in the blank.
  24. Why aren’t you already doing the thing you mentioned in the above question? What’s stopping you?
  25. What is my definition of failure?
  26. When I think back to a time that I failed, I feel …. Fill in the blank.
  27. What is my definition of perfection? Is it attainable?
  28. Do I hold myself to a higher standard than others? If so, why?
  29. In what areas of my life do I feel inferior to others?
  30. Have I ever sacrificed a part of myself to fit in with others better?
  31. Where am I playing small in my life?
  32. What narrative or stories do I tell myself surrounding ‘wanting more’?
  33. If I could tell my younger self only one thing, it would be …. Fill in the blank.
  34. When have you ever felt abandoned by those around you? Describe the situation and what it made you feel.
  35. How do I show up for others in ways that I don’t show up for myself?
  36. What do you need to forgive yourself for?
  37. What is the thing you feel most guilty for in your life to date?
  38. ‘I am overly critical and harsh on myself’. Do you agree or disagree with this statement and why?
  39. ‘I feel the need to keep myself hidden and small for the sake of others’ feelings’. Explore this statement.
  40. ‘I’ve stayed in relationships (either platonic or romantic) that deep down I knew weren’t good for me. Why did I do that?’ Explore this statement and the feelings it brings up.
  41. ‘I am worthy of good things coming my way’. Do you agree or disagree and why?
  42. If you were to live the remaining years of your life as an exact repeat of what has gone by, how would you feel and why? Where would you make changes?
  43. Describe the time when you felt the most alone.
  44. ‘In the past I have let people take advantage of me’. Explore this statement.
  45. Does acknowledging that other people have taken advantage of you bring up any anger, resentment or uncomfortableness? If you could turn back the clocks, what would you do differently?
  46. Where do you need to set better boundaries in your life?
  47. Did your parents always address and meet your needs as a child?
  48. Did your teachers and school peers treat you with the respect and love you deserved as a child?
  49. Thinking back to a time in my childhood when I felt different or outcast, do I notice any similarities in that moment to how I go about my daily life now? Are there childhood fears appearing in my adult life?
  50. What makes you really angry, so angry that you don’t tell anyone or you internalize and bury it?
  51. What is my inner truth?
  52. If I had to take a negative experience and reframe it positively, how would I do that? How does the process of reframing make me feel?
  53. What is my deepest source of rage and anger?
  54. What can’t I accept about myself?
  55. What do I hate about others? 
  56. What do I need to stop running away from? What do I struggle to tackle head on?
  57. What is the greatest lie I keep feeding myself with? Where has that come from?
  58. How far have I come in life?
  59. What does happiness mean to me?
  60. Who am I?


Each of these shadow work questions were designed to help you become more self-aware. The simple act of writing down your true, unfiltered thoughts and reactions to these questions means you’ve achieved that goal.

But what you do next with all of this information depends on your personal goal. Some are happy to leave shadow work in their journal and use it as a trusty tool to rediscover themselves after periods of confusion or overwhelm.

Others like to dig deeper and implement changes (both big and small) into their lives as a result of what they discovered during their journaling sessions. Either approach is valid. 

The key to making changes as a result of shadow work lies in your ability to analyse your answer to figure out the core theme or emotion lurking underneath.

Then, taking that emotion and trying to connect it with a past experience, traumatic event or time when a belief was challenged is the next logical step in the healing process.

Note, there will be times when you say ‘I don’t know where that came from’, and that’s perfectly normal. From my own experience, and the observation of my trainee counselling sessions with clients, these answers and connections will come to you at the most random of times.

Once you’ve gained some kind of understanding of your answer and where it came from, it’s time to decide how you move forward with this information; do you pick a new path, do you choose a new perspective, do you vow to practice more self care, do you forgive yourself?

Whatever you choose, it’s important to be as gentle as possible with yourself.


I first delved into the realm of shadow work through journaling a few years ago. I was feeling completely lost, overwhelmed and apathetic with life.

I had an unexplainable crushing and sinking feeling that was slowly draining all the enthusiasm and love out of me, amongst many other things. And so, the logical and analytical part of my mind wanted to know the ‘whys’.

Surface level solutions and simple answers didn’t cut it for me. I knew something was triggering all of this, but what? That’s when I decided to take a good hard look at the aspects of myself that I buried for years on end. How unresolved traumas and past experiences were still playing out in my life.

It was through these very shadow work prompts and questions that I had many ‘aha’ moments of realisation.

Whilst not everything had an answer (and it never will – something I found hard to accept), I discovered that we suppress and continue to suppress what feels unacceptable to our innermost being out of fear of what we might discover.

‘Shadow Work is the Path of the Heart Warrior’ – Carl Jung