SHADOW WORK 400 PROMPTS

1. How judged do you tend to feel on a daily basis? Explore how much of that perceived

judgement is real and how much is imagined.

2. Take a look at the best and most enjoyable aspect of your life right now. What is your

underlying fear in that area and why?

3. Write about the last time you tried to manipulate a situation to your advantage and examine

how you feel about that in hindsight.

4. Describe a scenario in which you feel that competition could be healthy and productive.

Then describe a scenario in which competition could be toxic and unproductive. Finally, write

about your emotional response to this exercise.

5. What does it feel like to have your emotions belittled or downplayed? Be as descriptive as

possible and try writing about specific examples.

6. Pinpoint something that's really frustrating/upsetting you at the moment. Then try writing an

uplifting, beautiful poem about it!

7. Write about the last time you ran away from your responsibilities. Consider why you did

that and what the results were.

8. How can you begin to give other people more space and acceptance to be themselves

around you?

9. If you could say one thing to the person who's hurt you the most right now, what would it

be and why?

10. Consider yourself at your worst - at a point where all of your most negative and disruptive

traits have come to the surface. Capture that version of you in your mind. Then write a letter of

love, understanding and compassion to that version of you. (For extra credit: Read the letter

aloud to yourself whenever you feel like you've turned into a bit of a monster!)

11. What does the word 'punishment' make you think of right now and why?
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12. Write about the different ways in which people have expressed their anger or resentment in

front of you over the last few months. What do you notice about their different modes of

expression for these emotions?

13. What's the one thing you know you need to do but keep avoiding? Write it down. Then write a

step-by-step description of actually doing it. Include every action which would need to be

involved in order to get it done. At the end of the exercise, explore how you feel.

14. When was the last time you witnessed distinctly self-destructive behavior, either in yourself or

in someone else?

15. 1What was the last cruel thing you wanted to say to someone in order to make them feel bad

about themselves or their actions?

16. Whereabouts do you currently feel isolated and how are you dealing with that emotion?

17. Write about the biggest experience of loss for you so far this year.

18. What do you currently envy in someone else's life and why?

19. What does it feel like to be completely discouraged by someone's words?

20. Why is it sometimes difficult to tell the difference between someone saying something

intentionally mean and saying something accidentally thoughtless?

21. What does the term 'constructive criticism' make you think of and why?

22. What emotion do you try to avoid? what makes you afraid to feel it? what are you afraid will

happen if you feel it?

23. In what ways are you privileged? What do you take for granted?

24. What is the biggest promise you made to yourself that you have broken? how does that make

you feel?

25. How do you lie to yourself in daily life? What are you trying to avoid?

26. What do you think is your worst trait? Why is it "bad"? What positive aspects does this trait

bring with it?

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27. Think of a time someone broke your heart. could you have been responsible in some way as

well?

28. Do you hold grudges against someone? If so, why are you not letting them go yet?

29. What do you need to forgive yourself for?

30. Think back on the last time a person triggered you: can you see how the aspects of that person

that triggered you are also in you?

31. Think back on your last argument/fight: did you actively try to see the other person's viewpoint

and would there have been a way to be more compassionate with the other person and

yourself?

32. What negative or positive do others point out about you that you have trouble accepting?

33. What emotions do you rarely express around others and when did you start hiding them?

34. What are your triggers that cause you to get angry or defensive in the presence of others?

35. What qualities in your family members do you most dislike or have trouble dealing with?

36. When are you the most critical of yourself? Explore what your self-talk sounds like below.

37. Describe 5 things you love about yourself and feel gratitude about.

38. What am I addicted to?

39. How does the feeling of envy show up in my life? Where does this envy that i am feeling stem

from? How would I feel if I obtained the things that I am envious of?

40. How can I be kinder to myself?In what ways do I consciously or unconsciously punish myself?

41. What is a grudge/incident that I am holding onto? Why do I choose to hold onto this weight?

How can I let this weight go?

42. What are my strengths?

43. What are my weaknesses?

44. What am I thankful for?

45. What do I love about myself?

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46. What’s your biggest learning lesson from the past?

47. List all the people that you need to work on forgiving, and explain how they have hurt you.

48. Write about the saddest moment in your life.

49. Write yourself a letter of forgiveness.

50. Write about one of your exs.

51. If you could do something all over again what would it be? ( nothing doesn’t count).

52. Write a letter to your parents?

53. Why do you hang out/associate with the people you’re around?

54. List three things you want to change about yourself. Why haven’t you changed those things?

55. What do you still hold onto-regarding your parents?

56. If there was no chance of failure, what would you do?

57. Who do you miss right now? What do you want to say to them?

58. In what ways are you inauthentic? Why?

59. Have you ever badly hurt someone unintentionally? Could you been more

responsible/compassionate to them?

60. What rules do you intentionally break? What is your reason for breaking them? Are you truly

justified to break these rules?

61. Do you have any fetishes/kinks that stem from issues in your past? Do they liberate or hinder

your healing process?

62. Think of a time someone broke your heart. In what ways may have you been responsible as

well?

63. What is the biggest promise to yourself that you have broken? Do you regret it?

64. In what ways are you privileged? How often do you take things for granted?

65. What emotion do you try to avoid (sadness, jealousy, anger..) why are you afraid of letting

yourself feel that way?

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66. What friendships/ relationships do you hold onto that are unhealthy? Why?

67. In what ways are you hypocritical? Do you break your own rules of conduct? Hold others to a

higher standard than you hold yourself?

68. What are things you should absolutely never forgive if someone did to you? Have you done

any of these to others?

69. How can I cope with sadness in a healthy way?

70. How long do I need to forgive people and situations?

71. What did you survive? (Not just the type of abuse, but rather the who, the what, the where. Tap

into that hard place. Name it. Claim it. You survived it!)

72. What colors represent your pain? Why?

73. How do you (inner child) see me (adult self)?

74. What are you thankful for today?

75. What makes you feel safe?

76. What are your current short term goals?

77. How do you feel right this moment?

78. Write 10 positive affirmations.

79. What do you feel like you need to do in order to “recharge” ?

80. Why am I afraid of being true to myself when others are around?

81. When was the last time that I extended kindness to someone?

82. What aspect of my personality still needs improvement?

83. When was the last time I fell head over heels with life?

84. What does having confidence mean to me?

85. How can I stop negative self-talk?

86. How do I demonstrate self-love?

87. If I could ask my future self one question, what would I ask and why?
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88. Where do I see myself in 5 years?

89. Who does my support team consist of ?

90. When do you feel most-in tune with yourself?

91. How could you describe yourself to others?

92. How would others describe you?

93. How do you manage stress in your life?

94. What does happiness mean to you?

95. What makes you feel unsatisfied?

96. How do you lift your mood when you are feeling down?

97. Are content with your life at this very moment?

98. What calms you down when you are upset?

99. What do you wish others took the time to learn about you?

100. How can you step out of your comfort zone?

101. How do you spend your free time?

102. How can you be more productive?

103. What obstacles do you encounter with yourself?

104. In what areas in your life do you wish to spend more or less time?

105. What are the greatest insights you have gained?

106. How has your life changed for the better this year so far?

107. Where am I uprooting? Where do I need to put my roots back in order to keep growing?

108. Where do my thoughts wander? Are they resistant, victimizing, or pessimistic?

109. Am I letting people use me as an emotional and energetic punching bag?

110. How can I continue to be a light?

111. What do you spend time reading or studying about?

112. What are the things I need to say no to in order to make room for “yes” moments?
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113. What scary things would you like to do more of?

114. What new things would you like to learn? What is holding you back?

115. In what ways have you made yourself small?

116. Write out your anger and frustrations.

117. What are some of your loop thoughts or behaviors?

118. How do you feel about the trauma you have experienced?

119. What is my happiest memory?

120. What are your favorite physical characteristics and why?

121. Describe a time you felt valued and loved.

122. Write a missed opportunity you wish you had taken.What could you do differently next

time?

123. What do you look for in a close friend? Do you have those characteristics?

124. Are you a spiritual person? Describe your beliefs and/or doubts. How do those beliefs affect

how you live your life?

125. Are you doing what you truly want to do?

126. Is there anything you can't let go of but you know you should? And if so, why ?

127. Do you remember anyone you hated 10 years ago? Does it matter now?

128. What is the meaning of life? What is my purpose?

129. What are you holding on to that is limiting you?

130. What are you creating a toxic space for?

131. Do I say yes when I should say no? Why ?

132. How can I love myself more today?

133. What kind of thoughts am I nursing?

134. What relationships am I thankful for?

135. How can I be thankful for challenges that I've experienced?

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136. How can I be thankful for the changes that have occurred in my life?

137. How can I say thank you more?

138. Favorite childhood memory?

139. Least favorite childhood memory?

140. What are 5 principles I choose to live by no matter what it looks like?

141. When I feel triggered by anxiety or overwhelmed I choose to do what?

142. What are three things that help me feel alive?

143. What does giving and receiving love look like practically right now?

144. Has anxiety gotten better or worse this month & why do i think so?

145. Write a letter to your teenage self?

146. If you could run away, where would you go and why?

147. Share one of your innermost secrets, something you’ve never told anyone.

148. How would you like to be remembered when you’re gone?

149. What is your most treasured possession and why?

150. Who or what means the world to you and why?

151. Where does self-worth come from?

152. What do I need right now more than anything else?

153. Am I completely and truly free? Explain.

154. What do I value more- intelligence or wisdom?

155. How do I contribute to society?

156. How do I move past unpleasant thoughts or experiences?

157. What types of topics do I tend to avoid? Why?

158. What keeps me awake at night?

159. What do I admire most about myself?

160. What are the things that get in the way of my happiness?
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161. What does the perfect day look like?

162. Do I have unfinished business with someone?

163. Do I value my personal privacy?

164. If I could redo yesterday, what would I do differently?

165. Am I self-sabotaging? If so, why?

166. How do I trust myself? Do I listen to others more than myself?

167. Do I surround myself with mostly postly or mostly negative people? How does that work for

me?

168. How do I feel about my relationship with my body?

169. Do I feel seen, heard, and valued?

170. Which person in your life makes you act like someone else?

171. Which person in your life can you be 100% yourself with?

172. Are you where you thought you would be at this point in your life?

173. If you could go back to school to pursue something different would you?

174. What is your favorite quote and why?

175. What do you love most about your personality?

176. Describe your dream home in detail.

177. Name someone you wish you could talk to more about things?

178. Name 5 things you are thankful for.

179. Could I be a better listener for others? If so, how?

180. Name of selfless act you performed lately.

181. What can people always expect from you, day in and day out?

182. Do you often daydream of a different life? What does this dream look like?

183. How do you feel when you receive a compliment and why?

184. How often do you talk negatively on a daily basis?

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185. What would your life be like if you stopped talking negatively?

186. What is the biggest achievement you have ever gotten in life?

187. What do you wish your partner would change about themselves?

188. What do you think your partner wishes you could change about yourself?

189. Do the people you care about the most know much you care about them?

190. How long have you been holding onto anger about something from your past?Name

solutions on how to move past that.

191. Do you think feeling unhappy is ok or not ok? Why?

192. Name a red-flag you are ignoring in your life.

193. Do you feel connected to your culture?

194. What do you enjoy about adulthood?

195. Do you think time heals all wounds? Why or Why not?

196. Do you believe people really can change?

197. Am I thinking negative thoughts before I fall asleep?

198. Am I taking care of myself physically?

199. Am I letting matters that are out of my control stress me out?

200. If I had to instill one piece of advice in a newborn baby, what advice would I give?

201. What small act of kindness was I once shown that I will never forget?

202. Is it more important to love or be loved?

203. Name the biggest “what if” in your mind.

204. If you have children, what would you recommend them to do or not do?

205. How do you deal with criticism?

206. Do you prefer to lead or to follow? Why?

207. If present day me could talk to myself from 10 years ago, I would say

208. How I spend my days is how I’ll spend my life. How do I feel about that?
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209. My ideal day starts with …

210. Getting triggered unexpectedly can be a positive thing because…

211. When I think about my life in the present, I am most proud of…

212. What are the current and recurring problems in my life? What would happen if I started

viewing problems as opportunities?

213. What I want and what I need are not always the same.

214. A rejection can point me in the right direction. An example of this in my life is…

215. When I think about my future, I am most excited about…

216. I can’t fix, change or improve anyone. I can only inspire. How can I lead by example?

217. Do I actively listen from my heart? Or do I analyse with my mind? Which is more likely to

help and heal others? Why?

218. I feel happy and confident in my body when I …

219. I really want recognition for…

220. I really wish others understood this about me…

221. What does ‘freedom’ mean to me? What does it feel like?

222. I felt especially valued and loved when…

223. When I think about my future, I am most afraid of…

224. Am I a spiritual person?

225. Do I project aspects of myself onto others?

226. When I think about my future, I am most excited about…

227. What’s the last compliment you received?

228. Write a love letter to your body thanking it for carrying you and keeping you alive.

229. What compliment do you want the most? Give it to yourself.

230. Write down the positive ways you’ve changed over the past five or ten years

231. Write a letter to yourself accepting yourself for who you are
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232. Write down ten positive affirmations that you can recite when you’re overwhelmed by your

insecurities.

233. What are three simple ways you can love yourself every day?

234. What’s one thing you’ve done (no matter how small) that you’re proud of yourself for?

235. Write down five positive things you can tell yourself instead of the typical negative self-talk.

236. What flaws and mistakes can you forgive yourself for?

237. What makes you feel loved?

238. What’s a kind, level-headed way to respond when people make fun of you?

239. What sets your heart on fire, and why do you love yourself for that?

240. How can you make sure to fill your cup before giving yourself to others?

241. What do you feel like you need the most right now, and how can you meet that need?

242. If your closest friends were to write down your best personality traits, what would they be?

243. How can I meet my insecurities, mistakes, and flaws with grace, acceptance, and love

today?

244. Picture all the people you feel judged by, and one by one write down why their opinions of

you are wrong.

245. If you struggle with self care, what are the top reasons you neglect taking care of yourself?

246. What’s the first thing you turn to when you feel sad? Is it a healthy thing?

247. What are ten things you’re grateful for?

248. Whose approval do you want the most, and why?

249. What hobbies did you have as a kid that you dropped? Why did you drop them?

250. You’re at your happiest when you’re . . .

251. What have you purposely skipped out on, even if you wanted it? What stopped you?

252. What motivates you the most (fear, money, happiness, etc.)?

253. Write down a definition of who you are—the good and the bad.
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254. What activities drain your energy the most?

255. What activities give you energy?

256. After spending time with someone, do you typically walk away feeling loved or judged?

257. Do you assume people judge/dislike you based on past experiences? How can you work

through that?

258. What are your three biggest pet peeves?

259. What’s your biggest insecurity?

260. Who inspires you the most and why?

261. If money wasn’t an issue, how would you live the rest of your life?

262. What negative or traumatic experiences have you let define you, and how can you walk

away from them?

263. What are you afraid of the most?

264. What things have you loved doing all of your life?

265. What thought patterns have you noticed lately, and are they healthy or toxic?

266. Where would you be if all of your goals were accomplished?

267. What goals have you let fall by the wayside?

268. Do your current goals align with your core values?

269. What would your highest self say to your current self?

270. What’s a limiting perspective or mindset that you’ve lived with your entire life?

How are you going to work through it?

271. Write down one good habit you want to start working on.

272. What are your biggest time wasters?

273. What changes do you want to see in your life in five years?

274. How can you brighten up your loved ones’ days?

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275. What do you want to be remembered for, and how can you work toward that?

276. How can you stay on top of your goals and New Year’s resolutions?

277. What past experiences am I still healing from that I need to give myself grace for?

278. What dreams do you need to put on hold for right now so you can pursue your

purpose?

279. What gets you out of bed in the morning? Are you pursuing that daily?

280. What things am I willing to let go of so I can live my best life?

281. What habits, memories, relationships, etc. are you holding onto that are keeping you from

improving yourself?

282. What boundaries do you need to set with others and yourself to prioritize your goals and

self care?

283. When do I feel most confident in myself, and when do I feel the least confident in myself?

284. What would your life look like if you were fully confident in yourself and your opinions?

What steps can you take to get closer to that?

285. Allow yourself to think about what your ideal life would look like, and then write it all down.

286. What are 10 things you are really good at?

287. What are 5 physical features you love about yourself

288. What are 3 of your strongest qualities?

289. Write out your ideal vision of your “dream life”

290. What are 3 goals you want to accomplish before the end of the year

291. Write out a gratitude list of things you are thankful for

292. Write out 10 positive affirmations

293. What are 5 of your best personality traits

294. How can you love yourself more?

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295. Write out a perfect morning routine to stick to

296. Write out things you forgive yourself for

297. What are 3 ways you can take actionable steps towards your dreams?

298. What do you love most about your life?

299. How can you improve your mindset so you love yourself more?

300. Write yourself a love letter

301. What are 5 things you have done that make you proud?

302. What bad habits and mindsets do you need to quit?

303. What are 10 things that make you the happiest?

304. Write a positive advice letter to your future self.

305. Describe yourself positively in 10 words

306. What’s standing in the way of your happiness and what can you do to fix that? (Positive

thoughts only)

307. What are 5 good habits you want to start next month?

308. What are 5 flaws that you accept and how can you look at these flaws in a positive light?

309. Write yourself a thank you letter

310. Make a list of all your emotions right now - what comes to mind first?

311. Think of the worst emotion or feeling you have right now and write about it

312. Think about the best emotion or feeling you have right now and write about it

313. Do you remember what your first panic attack was like?

314. How did you find relief from the first panic attack?

315. Describe your worst panic attack ever - how did it start?

316. If you have anxiety, what are some things you do to help manage it?

317. List 10 things that made you smile today

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318. List 5 things you are currently stressed about

319. List 5 things causing you stress, but that YOU have the ability to change.

320. What situation makes you most fearful?

321. Is your anxiety worse in public or at home?

322. Is your anxiety tied to a memory or experience?

323. How is the way you deal with stress different now than when you were younger?

324. What has your stress taught you about yourself.

325. If you could write a letter to any one fear, which one would it be?

326. Write about what you love about your life right now - think of only positive things.

327. Write about what you wish you could change, and what is required to change them.

328. Share gratitude for 3 people who are supporting you at this point in your life.

329. What are some internal thoughts that make you feel worse?

330. What is something you tend to dwell on?

331. If you could achieve anything in your life, what would it be?

332. What do you think is holding you back from achieving that goal?

333. When was the last time you faced one of your fears?

334. What are some songs that always cheer you up? Turn them into a playlist.

335. Make yourself 10 promises and detail each one.

336. What do you feel is going wrong in your life right now?

337. Do you think your life is living up to your expectations?

338. What is something in your life that is the biggest surprise?

339. What is something going right in your life?

340. How can you improve your mental health?

341. Name a time when your mental health suffered, but you improved it. What helped?

342. When times get tough, what is something you need to remind yourself?
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343. Make a list of your greatest qualities and show appreciation of them.

344. List 3 things you would do if you weren’t afraid.

345. What makes me cry?

346. Which words can annoy me?

347. What makes me anxious?

348. What can make me mad?

349. How can I uplift my mood?

350. What makes me laugh?

351. Which type of joke makes me feel offended?

352. What scares me the most?

353. Are there things that I still need to forgive myself for?

354. Are there people I still need to forgive?

355. Which past events or experiences still bother me?

356. What are some of the biggest mistakes I made and what did I learn from them?

357. Which childhood memory makes me happy and which makes me sad?

358. What impact do I want to have on this world?

359. How do I want people to remember me?

360. Do I want children?

361. Where would I like to live?

362. What do I want to be able to do before I die?

363. What kind of career do I want?

364. What can I see myself doing every day until I retire?

365. Do I want to have a 9-5 job or my own business?

366. Do I like my job?

367. What did I want to be since I was a child?

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368. Why did I want to be that?

369. Do I still want to be that?

370. Why did it change?

371. What subject in school was my favorite

372. What are my hobbies?

373. What smells do I like?

374. Which type of event excites me just thinking about it?

375. What do I like to talk about?

376. What kind of people do I like hanging out with?

377. How do I like to spend my birthdays?

378. What type of presents do I love?

379. What type of music do I like?

380. Do I like pets?

381. What kind of games do I like (or do I even like games)?

382. What beverage is my favorite?

383. Which skin care products do I like the most and why?

384. What hair care products do I like the most and why?

385. What activities do I dread doing?

386. Why do I dislike these activities?

387. What type of foods are my favorite?

388. How do I like spending alone time?

389. What is my favorite color?

390. What type of movies do I like?

391. What do I love the most about my body?

392. What are the things that I need to change in my personality?

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393. In my opinion, what are my best qualities?

394. What does a perfect day look like to me?

395. What does a perfect date look like to me?

396. Do I want to be in a relationship?

397. What do I expect from a relationship?

398. Do your actions match your word?

399. A mistake that made you grow?

400. A quote that inspires you.