Shadow Work Prompts
How can you be kinder to yourself? In what ways do you punish yourself?
What are your greatest dreams? How are you holding yourself back from these dreams? What personal sorrow or heartache are you holding on to that may be keeping you from being the greatest version of yourself?
Are you willing to feel uncomfortable at times when you need to grow and change? Take a look at the best and most enjoyable aspect of your life right now: what is your underlying fear here? Does this fear stem from something in your past?
How important are you to yourself? How high do you prioritize yourself? Do you constantly prioritize others and their needs above your own and if so, why?
Write a letter of forgiveness to yourself. Forgive yourself for the things you tolerated and accepted because you didn’t know better.
Do you think asking for help is a sign of weakness? Why? What keeps you from asking for help from others?
Do you hold a grudge? Why? Who are you currently a grudge against? Do you think letting go of your grudges will benefit you in any way? How do you feel when you have to cut ties with those who are harmful or toxic to you?
Which one of your mistakes taught you the most this past year? What did you learn? What lessons can you take from similar situations?
What aspects of yourself do you project onto others? Are these positive or negative qualities? What aspects of yourself do you repress or deny?
Is there an incident causing resentment that you have been holding onto? Why do you choose to carry this weight? How would you feel if you let go of this situation?
How do you handle criticism from others? Do you get defensive? Why? What part of you feels like criticism is a personal attack?
In what ways are you self-deprecating? Do you find yourself using humor to do so? How do you feel after you make a joke at your own expense? Do you do this to avoid facing your real feelings about yourself?
When you feel jealous of someone else, what is your jealousy usually tied to or stemming from? What does this person have that you feel you lack or experience a lack of?
What are you still holding on to in regard to your parents? Write a letter to them expressing your emotions either currently or from your childhood.
When was the last time you demonstrated love to yourself? How do you show self-love? Do you give more love to others than to yourself? Why?
Write a letter to your younger self, either at a specific age or just generally younger. What advice can you give to your younger self? What would you tell them about a hardship they may be experiencing? Acknowledge any emotions that come up while writing this.
What do you notice yourself doing or saying to yourself that is unkind or judgmental? Would you talk to a friend or loved one the same way you speak to yourself? In what ways can you try to be more kind and accepting towards yourself?
What do you need to stop running away from?
Do you find it hard to forgive? Do you say “it’s okay” when it really isn’t? Why? What aspects from your past have made it difficult for you to forgive others?
What is your biggest struggle with loving yourself? What can you do to incorporate more self-love into your life? What self-limiting beliefs do you currently hold?
Do you have trouble managing your expectations? What do you feel when things don’t go your way? Are you able to recover from setbacks without dwelling on them? How do your expectations tie into your sense of entitlement?
Do you find yourself reacting to others feelings or needs more than you react to your own? Think of a time you honored your own feelings and desires above anyone else’s and how you felt afterwards and the result of doing so.
Write down your idea or definition of what “confrontation” means. Write about a time you feel you successfully accomplished confronting something or someone and a time you avoided doing so and why.
Do you shy away from confrontation? Why? Address any reactions you have to the word. Examine what gave you a bad idea around the word or act and release it. Appreciate your survival.
What is a story about you that is told, but not entirely true? Do you tell it, or do other people? If others tell it, do you correct it or perpetuate it?
Describe your shadow self. Try to avoid demonizing it, as darkness is not inherently bad. What form does it take? Use your description to make a quick drawing of it if that helps you with visualization.
How has your shadow helped you? Is there a time in your life that you had to rely on those qualities? What led to that situation? What/who brought that out of you? Acknowledge and release any emotions from the past. Thank your shadow for protecting you.
Think of a person that you hate for “no reason”. What about them bothers you? Are these things a projection of your own making? Do these things remind you of yourself or someone who hurt you?
Do you believe in unconditional love? If not, why? Is your love for yourself conditional? Does your disbelief in unconditional love create transactional relationships in your life? How do those relationships make you feel?
Are you scared to allow changes in/to your life? What about self-imposed change, does that scare you as well? Why? Is it a fear of failure? Are you afraid that you will try to be better and prove your negative self talk right?
Do you apologize? How often and for what? Do you find yourself saying “sorry” for existing or taking up space rather than any genuine offense to another person?
Do you engage in unnecessary snobbery to boost your ego? When do you find yourself exercising a superiority complex? What things do you feel the need to be superior to others about?
What is one quality you wish you had? Who around you has this quality, do they inspire you to be more like them in this way? What is stopping you from embodying this trait yourself?
What makes you feel close to people? What conditions have to be met to feel closeness? What builds that feeling? Can you be close to someone without trust, why or why not?
List a few coping mechanisms that make you feel bad or guilty. Why do they make you feel that way? What are you using them to cope with? Is there a healthier method of coping with this feeling/situation? What is it and what would it look like for you?
What are your morals? How do those morals make you feel? Do you find yourself betraying them or are you able to stand firm on them? Do they come from you or someone else?
How easily do you give up? Why? What have you given up on in the past? Was it sensible to do so or were you abandoning your self/idea/dream out of fear?
What traits do you consider virtuous? Do you embody any of these things or are they solely qualities you admire about others? Do you have a hard time thinking of yourself as virtuous or “good”?
Do you value your intelligence and intuition? Do you trust yourself to make your own decisions (big and small) or do you rely on others to decide for you? How often and for what types of situations do you ask others for second opinions?
How important is privacy to you? What things do you consider a violation of your privacy? How do you react to these things? What things do you believe require privacy? Are you willing/able to communicate this belief to others or do you just assume that others should agree?
List any traits of your loved ones you do not like and find hard to deal with or accept. Do you share any of these traits? Is your behavior any more or less acceptable than theirs? Why?
Think of a time you were hurt but felt that you deserved it. What made you feel that way? How and why did you justify the act? Was it your actions leading up to the act, your self esteem at the time, or something else? Do you still feel like you deserved to be hurt?
Do you prefer to identify with or against people? If against, why? Does outcasting yourself first make you feel like you’re in control?
Do you use relationships based on identifying and relating to others or not to compare yourself to others? Can you another person/their feelings even if you do not share an experience or point of view?
Do you have a particular self-destructive act or form of self-harm you engage in? Do you have a particular love language? Do you notice any connection between the two?
What do you reward yourself for and how do you reward yourself? Are you able to enjoy your accomplishments or do you find yourself constantly unsatisfied after you’ve achieved or completed something?
Are you living true to yourself? Do you change who you are based on who you’re around? What changes do you make and why do you make those changes? Does the idea of living authentically scare you? Why?
Make a list of things you find yourself frequently complaining about. Are these things unchangeable? If they are, what is keeping you from accepting them? If not, what is stopping you from moving on/through them? Do you use complaining/venting to avoid the physical and emotional work of changing your circumstances?
Is kindness ever hard for you to accept? Do you ever reject acts of kindness or niceness from others and if so, who are you rejecting and why? If you feel undeserving, when and how does kindness trigger this feeling?
Is it ever okay to hurt someone? Think of a time you hurt someone, was this on purpose or on accident? Was it in retaliation or self defense?
Have you hurt someone by choosing yourself? Have you ever had to apologize for your boundaries or personal feelings? When made to choose, do you pick your comfort and happiness or someone else’s?
Do you express gratitude for your life? If so, how? What are you thankful for? Nothing is too small. If you don’t feel like you have anything to be grateful for, start making a list of things that bring you happiness, contentment, or make your life easier.
What was the last cruel thing you wanted to say to someone? Was it to make them feel bad about themselves or their actions? Write it out and explain how it would’ve made you feel better and if it would have solved the conflict or not.
Do you value rest or do you avoid it? Does hard work bring you joy? Do you measure your personal value through your productivity? Explore why. Are you focusing on your own business/goals or the business/work of others when you notice yourself measuring your worth like this?
How do you prefer to be apologized to, if at all? Would you rather someone change their behavior than verbally apologize? When you are slighted, how do you make it known to the person who hurt you? Do you let time pass before telling them and if so, why?
Write a list of things or people you feel obligated to and why. Are you choosing to dedicate yourself or do you feel forced to give your time and energy to these things/people? Does honoring your obligations feel good or not? What might happen if you stopped performing these duties for one whole day?
When is the last time you gave yourself a reward? What is your relationship to self reward versus self punishment? Take time to make a list of recent accomplishments and suitable rewards for them. Appreciate your effort and hard work actively today.
How do you view revenge? Do you want personal or first hand revenge or do you prefer to better yourself and life? Are you able to move on from a situation without revenge? Has going after someone for the sake of revenge ever solved your problem with them or soothed your hurt feelings? Why or why not?
How much do the opinions of others matter to you? Does your self opinion change based on the views of others in your life? Do you trust and value your opinion of yourself more than the feedback you get from the world?
What unhealthy attachments (people, things, feelings, habits) do you hold on to? What fears, if any, do you have around ending these attachments? Make a list of pros and cons to having and ending these attachments to help you consider releasing them.
Make a list of ways you frequently criticize yourself. Are your criticisms discouraging and abusive or constructive and motivating? Do you believe in your ability to improve? Is the way or reason you criticize yourself for improvement or punishment?
Do you have commitment issues? Do you struggle to follow through with your plans and promises? How often do you make excuses for your lack of follow-through and what areas do you notice yourself doing it the most in your life?
Describe at least five things you love about yourself. When are you able to exercise these parts of yourself the most? How often do you acknowledge the parts of you that you adore? How does it feel to appreciate yourself with undivided attention?
What emotions are you most comfortable feeling? Do you default to one of these even if it is inappropriate for the situation you’re in? Choose one feeling you’re uncomfortable with and explore why.
Comfort is found in thorough exploration. What parts of yourself scare you enough to avoid? How do you avoid yourself? When confronted, do you make excuses for neglecting self exploration? If so, list them. Rewrite this list with the title “what is stopping me from being whole” and reflect on how you feel about making excuses for that.
What character traits in others do you recognize as a threat to your self-perception, ego, or safety? What part of yourself feels threatened? Do you often think people have hidden motives for interacting with you? Have you ever been wrong about someone having ulterior motives?
When someone doesn’t share your point of view, do you try to dehumanize them? When you catch yourself doing this, notice who you do it to and what situation or topic it is tied to. How does dehumanizing others to invalidate them make you feel?
Do you have a defining moment of your life? Is it negative or positive? Did you choose this moment or do you feel like others chose it for you? Is there a moment that you would replace it? How would having this new moment define you affect the way you think and feel about yourself?
Do you show kindness to others without any catch or strings attached? Are you able to be nice or giving towards others without expecting anything in return? Does being kind freely feed into your fears of being taken advantage of, why or why not?
When was the last time you tried to manipulate a situation to your advantage? Examine your behavior and your reasoning for doing so. Does manipulating people or things make you feel good? What fears do you have surrounding a lack of control that may cause you to act this way?
Do you fear rejection? When and how does this fear present itself? Do you hold back your thoughts and feelings even in crucial moments because of it?
How does competition make you feel? What are you motivated to compete for? If you dislike competition, describe the situation that caused this. Now, describe a scenario in which you feel that competition could be healthy, productive, and fun.
Do you try to make people change in order to suit your needs and wants? Are you able to accept and love people how you found them? How can you begin to other people more space and acceptance to be themselves around you?
Is there something about yourself that you withhold from people until you believe they can handle it or care about you enough to not leave? What do you fear about sharing this part of yourself? Is this fear holding you back from trusting others or having more intimate relationships?
Who did you want to be like when you were young? What qualities do/did you admire about them and why? Do you possess any of these qualities now? Do you still think of this person fondly or not?
When you reflect on your childhood, do you have a moment that seems to always trigger you? What emotions does it bring up for you and how do you process them? Are you able to handle those feelings in a healthy or constructive way?
How long do you reflect on your failures or mistakes? Do you have difficulties in coming to terms with them and accepting the situation? Do you suppress such experiences and the feelings that come with them?
What parts of yourself do you reject or had previously rejected? What is it about these parts of you that you deem unacceptable? Did they become unacceptable after someone else rejected or shamed them/you? How does honoring and engaging with these parts of yourself make you feel?
When and where do you feel the most safe and loved? Do you have access to these spaces daily? Do you give yourself time in these spaces as part of routine self care or do you make yourself earn it?
Do you satisfy your need for attention? If so, how? Do you embrace this part of yourself or reject it? Do you attempt to stifle it and if so, reflect on how well that works for you. Are you able to seek attention in positive ways or not? What is it about negative attention that appeals to you?
When do you feel uncomfortable, drained, or out of alignment? Are you able to communicate these feelings in the moment or do you hide them? If you do hide your feelings, reflect on when and why. How could setting a boundary lessen these feelings or experiences?
What kind of self-care do you prioritize? What kinds of self-care do you WANT to prioritize? Is there anything or anyone stopping you from doing so?
Consider possible and realistic ways to prevent or limit discomfort, being drained, or being out of alignment. How do you feel when you envision setting boundaries?
When you set boundaries, how do you feel? How do others react to your boundaries? If their reactions are negative, does this make you retract the boundary or feel like you have to do so or does it make you enforce the boundary even more?
What does discipline look like to you? When you decide to change or do something, are you able to do it when the time comes no matter what or do you find yourself making excuses to avoid it?
What brings you more pleasure: accomplishing personal tasks or helping others accomplish things? Do you enjoy feeling helpful or do you enjoy feeling needed? Are you able to offer help with no strings or expectations attached?
What does meaningful support from others look like to you? Can you identify your needs and communicate them to those around you? What behavior do you exhibit when your needs are not being met?
Do you lie to yourself? If yes, how often and what about? What is it about the truth that you reject and can’t accept?
Do you prioritize peace in your life? Are you able to make choices that allow you to experience ease or do you seek out conflict and struggle? What is it about conflict that you enjoy or feel you need?
What makes you feel confident? Do you give yourself permission to have this feeling or not? When you are being confident, is there anything that can trigger doubt in you? If so, what?
If you could rid yourself of any one memory or experience, which one would it be and why? How would you be affected by no longer having that be a part of you?
Do you try to heal familial wounds through your friendships? Do you often play a family role with friends in a way that reflects the kind of parent/sibling you wish you had growing up? What qualities do you wish this family member had?
How important is having a specific role to play or fill in relationships to you? Do have trouble with ambiguity in relationships? If yes, list the reasons and feelings this causes for you. Why do you prefer to have a role and what are the pros and cons of the role(s) you play?
What is your proudest moment so far this year? What about this moment stands out to you and makes you feel good? What can you take from this moment into your everyday life to instill pride in yourself?
What qualities in others are you drawn to the most? Are these qualities you share or qualities you want? What qualities do you have that you’re often surprised when people accept, love, or celebrate them?
What would your younger self be proud of you for now? What advice or words of comfort do you have for your childhood self?
What does good communication in a relationship look like to you? How do you distinguish secrecy from privacy?
How do you want people to remember you? Would you have to change anything about your behavior for this perception of you to become reality?
Do you feel that you need to be in a relationship to be happy or feel complete? Why?
Has your parents’ relationship affected your view of love?
Do you ever accomplish things just to prove yourself to others?
Are you able to risk failing at something in order to try new things?
What is your preferred method of communicating your feelings to others?
What is the ideal relationship to you? Do you consider any part of this ideal unrealistic?
Do you make an effort to get closer to other people or do you expect them to do all the work of building the connection?
Write down 10 things you’re holding back that you would say to people in your life if you had the courage.
What does your concept of unconditional love entail? Take a look at your relationships with others and see how it relates. In which of them do you see this concept realized?
How judged do you feel on a daily basis? Explore how much of that judgement is real and how much is projected.
Consider yourself at your worst point, then write a letter of love, understanding, and compassion to that version of you.
What is a promise to yourself that you have broken or continue to break?
Do you ever deny your needs or desires? What does withholding pleasure or comfort from yourself do for you?
What is your opinion of the world? Do you feel like you have a place in the world? How can you create or own your space?
Does your environment control your emotions? Are you able to remain at peace despite outside influences?
Is it hard for you to leave your comfort zone in order to experience new things?
Do you often find yourself over-thinking things you’ve said or done? What usually triggers this?
What is your relationship with your parents like? Are you inspired to be like them or not?
What is one thing you wish other people understood about you? How can you make this thing easier to understand?
Have you ever neglected yourself to give your energy to other people?
What experiences trigger you to overthink them?
How does overthinking affect you? What do you gain from doing this, what do you lose?
How do you speak to yourself when you’ve failed or been rejected?
Are you able to self-soothe? How can you either begin to learn or further develop this skill?
What parts of yourself do you feel neutral towards? How can you create a more loving relationship with these aspects of you?
How much does your appearance affect your self-esteem? Do you ever neglect appearance to punish yourself and if yes, what triggers you to do so?
What was your first intentional act of self care or self love? Is this still in your routine today?
When something triggers you, how do you respond? Do you allow yourself to feel those emotions or do you try to block out what comes up?
Observe your daily schedule. Are you giving yourself time to rest and time to focus on your own life and internal world? How can you make room in your schedule for this?
How do you define love? Is there plenty of love in your life?
What are 5 positive traits you’ve picked up from your parents?
What are 5 negative traits you’ve picked up from your parents? How do you feel about these, do you try to better them or not?
Do you treat others how you want to be treated or do you feel like you deserve special treatment regardless of your behavior?
Where and when do you feel the most entitlement? Why do you feel entitled, is it justified?
Have you ever lost a connection due to an impulsive reaction or response? How could you have responded to the situation better?
Do you get defensive or feel attacked when someone sets boundaries? Why or why not?
Describe a time you acted passive aggressively. How did your actions affect the situation or your connection with those involved? What would you have done differently?
Do you carry any guilt with you daily? Write a letter to yourself explaining why you blame yourself and discuss the source of your guilt. Apologize to yourself and anyone involved that you hold these feelings of guilt for, then write a compassionate and forgiving response to help release these feelings.
What is your relationship with solitude? Are you able to enjoy your own company? If not, what about being alone makes you uncomfortable?
Rate your discipline in each area of your life on a scale of 1 to 10. Where do you want to improve your discipline? Make a short list of ways to do so.
Do you always need for others to behave a certain way so you can be happy?
When are you most tempted to act impulsively or in ways that are unhealthy to you?
Do you get agitated or inspired by other people’s success?
How can you utilize solitude for growth? Do you allow yourself to create your own ideals without outside influence?
What areas of life are asking you to be more open? How can you expand your perspective in these places?
How do you define failure? When you find yourself failing, how do you treat yourself?
Do any of your pleasures make you feel guilty? Do you hide, downplay, or mock anything you love as a defense mechanism?
How much of your identity is tied to your job/career?
What does it mean to be strong? Do you acknowledge your own strength?
It is easy to learn from failure. What have your victories taught you about yourself and others?
