- Are you 100% yourself around others? Do you put on a persona or mask to blend into the crowd? Do you know who you are?
- Are you comfortable in your skin? If there is something that you would like to change about yourself, what is it and why?
- Are you happy to be alone in your own company? Do you use other people to fill a void?
- Are you happy with where you are in your life? Is there anything that you can do to improve it?
- Did you have any heroes growing up? Who did you look up to and why?
- Do you accept yourself as you are?
- Do you enforce boundaries with others or are you the type to let people cross lines?
- Do you ever find yourself manipulating people in an attempt to protect yourself?
- Do you ever have physical reactions to emotional feelings? Write about these. Why do you think this happens?
- Do you feel as though people respect you?
- Do you feel misunderstood? If yes, what misconceptions do people have of you?
- Do you forgive yourself when you have done something wrong? When you make mistakes can you move on from them or do they continue to hurt you?
- Do you form obsessive or unhealthy attachments easily? Why do you think this might be; do you have a fear of change/abandonment/rejection? Or, on the other hand, do you find it difficult to form emotional attachments; do you struggle with commitment or get restless staying in one place for a certain amount of time? Where do you think this stems from?
- Do you have any other traumatic childhood memories?
- Do you have any unhealthy attachments or habits? What are you doing to curb them and why have you continued to entertain them?
- 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?
- Do you lie to yourself to avoid addressing your fears?
- Do you often find yourself over-thinking what you’ve said or how you’ve acted? What usually triggers this?
- Do you practice self-care? Is there more that you could be doing for your wellbeing?
- Do you respond well to constructive criticism? Are you over-sensitive to any form of feedback? Do you allow yourself to be vulnerable in your romantic relationships? Do you put up walls around yourself and your partner or are you completely open?
- Have you ever broken a promise to someone else? Why? When you really think about it, is there any area of your life you’re in denial about?
- Have you ever broken someone else’s heart? Was it unintentional or intentional? Write about this.
- Have you ever had your heart broken? Write about this time in your life.
- 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.
- How did you deal with trauma in the past and what do you do to combat it in the present?
- How did you process emotions as a child, teenager, and young adult? How do you process negative emotions now? Has this changed over time?
- How do you carry the weight of your past trauma? How has it affected you?
- How do you deal with negative emotions now?
- How do you enforce boundaries? How do you feel when people overstep them? How do you react?
- How do you feel about confrontation? Why do you think this is?
- How do you feel about who you are as a human? Why? How often do you forgive yourself? What kind of things do you feel you need to be forgiven for? Why is this?
- 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?
- How do you fill your time when bored?
- How do you perceive failure? What is your definition of failure? How does it make you feel? Are you afraid of it? Why might this be? How did your parents/guardians react to failure?
- How do you plan to move forward after hurting yourself?
- How do you react when you’re angry? Is this similar to other people who have been in your life since childhood? Why do you think this is?
- How do you think people see you? How would they describe you? How do you feel about that?
- How do you view asking for help? Is it a sign of strength or weakness? Why is this?
- How does drama make you feel? Are you dramatic yourself? Do people call you dramatic? How do you feel about this?
- How have you moved forward from hurting someone else?
- How were you taught to deal with emotions as a child?
- Is there anyone in your life that you are competitive with? If yes, what caused this rivalry?
- Is there anyone you hold a grudge against? If so, what is holding you back from letting go and moving on?
- Think about one time where you’ve felt betrayed. What would you say to the person who broke your trust?
- 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?
- 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.
- 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.
- Think of a relationship you’ve walked away from. Write down the reasons it’s been a positive life choice.
- Was your childhood negative or positive? Outline the most prominent memories that you have of your younger years.
- What are the first signs that your mental health is dipping?
- What are three main goals you want to achieve with your shadow work?
- What are your core values as a human being? What’s the most important to you? What are you morally passionate about?
- What are your parent’s best and worst personality traits? Do you see any of them within yourself?
- What are your parents’ best/worst attributes? How are you alike/unlike them?
- What are your preconceptions about femininity? Why do you think this is? Where did they come from?
- What are your preconceptions towards masculinity? Where did these come from?
- What are your toxic traits?
- What are your toxic traits? How do these present themselves? How do you project these onto others?
- What are your triggers and what caused them?
- What aspects of yourself would you like to improve? Why? Has anyone in your past ever made comments suggesting that you should? If so, how did this make you feel?
- 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?
- What characteristics and traits do you dislike in others?
- What could have made your childhood better? How do you feel about that?
- What do you consistently lie to yourself about?
- What do you dislike about yourself most?
- What do you lie to other people about? Why?
- 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.
- What do you think are the worst character traits a person can have? When is a time you have demonstrated these traits?
- What do you wish people understood about you? How might you be better able to demonstrate the quality that people tend to overlook?
- What does freedom mean to you?
- What does the term ‘Shadow Work’ mean to you?
- What emotions do you tend to avoid?
- What emotions tend to bring out the worst in you? Why do you think that is?
- What gives you enjoyment?
- What in your life gives you the most purpose?
- What is something that you’ve always wanted to confront someone about? Why haven’t you? Do you plan to? Why?
- What is the biggest lie you consistently tell yourself? Why?
- What is the meaning of life to you?
- 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?
- What is your biggest regret and why?
- What is your deepest, darkest fear?
- What is your relationship like with your family? Has your connection strengthened since you were a child or has it gotten worse?
- What is your relationship with your parents and/or siblings like? How was it as a child compared to now? Why do you think this is?
- What lies have you previously told yourself? Are you being entirely truthful with yourself at this time in your life?
- What makes you feel most valued?
- What makes you feel unsafe? Explore this.
- What makes you self-conscious around others?
- 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’.
- What misconception do people have about you? How does that make you feel?
- What misconceptions have you noticed your harbour? Can you think about where these started?
- What most frightens you? How might you be able to expose yourself to that fear in a safe way?
- What negative emotions do you actually feel quite comfortable sitting with? Why might this be?
- What negative emotions do you tend to avoid? Why might this be?
- 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?
- What parts of your parents/guardians growing up do you see in yourself now? When did these begin to become apparent?
- What person has hurt you the most in your life? Write them a letter telling them all the things you’d like to say.
- What self-care do you regularly practise?
- 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?
- What situations make you feel less than or not good enough? Why do you think this is?
- What tends to trigger envy for you? Why do you think this is?
- What things are triggers for you? Consider where those irrational feelings stem from.
- 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.
- What toxic traits have you recognised in your parents? How did it make you feel when you realised that your parents weren’t perfect? Do you also possess these traits yourself?
- What triggers you? Can you identify where this came from?
- What was one time you remember feeling wronged as a child? How did you react? Has this affected you into adulthood? How?
- What was the last argument you had about? Was it resolved?
- What was your last uncharitable thought? Did you voice it? Was it deserved? Were you being unfairly judgemental?
- What were your parents’/guardians’ core values while you were growing up? Do you hold these today or do they differ? How so?
- What would you most like to be recognised for?
- What’s a question you had as a child that you never got a real answer to? Do you have that answer now?
- What’s one trait you see in other people that you wish you had. Why do you not possess this characteristic yourself?
- What’s the biggest lie you’ve ever told and why?
- What’s the biggest promise to you that someone else has broken? How did make you feel? Why?
- What’s the biggest promise you’ve broken to yourself? Why? How do you feel about that?
- What’s the most hurtful thing you’ve done to yourself?
- What’s the most hurtful thing you’ve ever done to someone else?
- 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?
- What’s the worst thing you’ve ever done and why did you do it?
- 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?
- 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.
- What’s your favourite way to self-sooth? Describe your perfect self-care day.
- 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?
- When are you hardest on yourself and why?
- When are you hardest on yourself? Why? Where do you think this stems for? Why do you put yourself under so much pressure? Why are you so reluctant to be kind to yourself?
- When have you been self-sabotaging or destructive in your life? Examine how you were feeling at the time, and what triggered your behaviour.
- When is the last time you felt let down? Examine how you felt and whether it was truly rational, or if you were triggered.
- 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.
- Which traits would you least wish to be described as having? Why would it be so terrible?
- Who are you closest to in your life and do they positively reflect who you are? Are you holding on to people that don’t deserve your time and affections? Are you honestly happy in your relationships?
- Who do you envy? Why? How might you be able to work towards gaining the things they have that you feel jealousy towards?
- Who do you hold a grudge against? What is stopping you from letting it go?
- Who has let you down the most in your life? Are they still around? How do you feel about that?
- Who has the most influence over you? Is that healthy?
- 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.
- 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?
- Who or when last/regularly belittles or downplays your emotions? How does it make you feel?
- Write about a time where you messed up and needed forgiveness. Did you ask to be forgiven? Did you apologise? How did it play out?
- Write about a time you felt let down by someone you’d previously looked up to.
- Write about one person you’ve never forgiven. What happened and why did you not forgive them? Was it warranted? How has this event affected you going forward? Do you think you could forgive them now? How did you move on from this?
dec 14 2022 ∞
dec 14 2022 +