Here is an organized master list. Let’s add more. I urge you to start recording these today.
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Version 2.0 Of The Wisdom Keeper Question List.
1. Describe a time when you faced a significant challenge or obstacle. How did you overcome it?
2. What is the most critical decision you’ve ever made, and how did it change your life?
3. What are some important lessons you’ve learned in your life that you believe everyone should know?
4. What values or principles guide your life?
5. Is there a particular experience that shaped your outlook on life?
6. How do you deal with failure or setbacks?
7. What is the most significant achievement of your life, and what makes it so important?
8. What advice would you give your younger self if you had the chance?
9. How do you define success?
10. What are your thoughts on forgiveness and its role in your life?
11. Is there a particular person who influenced your life significantly? What did you learn from them?
12. What is the best advice you’ve ever received?
13. What do you believe is the role of love and relationships in one’s life?
14. How do you manage stress and maintain balance in your life?
15. How do you cultivate positivity and optimism in challenging situations?
16. What do you believe is your purpose in life?
17. How do you handle criticism and use it constructively?
18. What’s one thing you wish people knew about you that they don’t?
19. Describe a time when you had to make a difficult ethical decision. What factors did you consider?
20. How do you build and maintain meaningful relationships in your life?
21. What is the role of curiosity and continuous learning in your life?
22. How do you approach problem-solving? Can you share an example?
23. How do you define and measure personal growth?
24. How do you navigate conflict, either personally or professionally?
25. How do you stay resilient during tough times?
26. What do you think about the role of compassion in our lives?
27. How do you make decisions? What factors do you usually consider?
28. What are some habits or practices that have significantly impacted your life?
29. What are your thoughts on the role of perseverance and grit in achieving goals?
30. How have your beliefs and views evolved over time, and what prompted this evolution?
31. How do you define wisdom?
32. What do you believe is the biggest misconception people have about life?
33. What role has adversity played in shaping who you are today?
34. Can you share an experience where you felt a profound sense of joy or fulfillment?
35. What role does gratitude play in your life?
36. What has been your biggest regret, and what did you learn from it?
37. If you could change one thing about the world, what would it be and why?
38. What does a meaningful life look like to you?
39. How do you approach understanding a perspective that differs significantly from your own?
40. How do you stay motivated when things don’t go according to plan?
41. What life skills do you believe are most important for younger generations to learn?
42. How do you maintain self-discipline?
43. What are your thoughts on the importance of legacy? What legacy would you like to leave behind?
44. How do you incorporate mindfulness into your life?
45. Can you share a moment that made you profoundly rethink your beliefs or perspective?
46. What’s the best way to cultivate creativity in everyday life?
47. How do you embrace change and uncertainty?
48. What is your perspective on the importance of self-reflection?
49. What do you think about the concept of lifelong learning?
50. What role does empathy play in your life and relationships?
51. How do you nurture the relationships that are most important to you?
52. How do you build trust with others?
53. Can you describe an instance where a failure led to an unexpected success?
54. What is the most challenging aspect of aging, and how do you navigate it?
55. What do you wish younger generations understood better about life?
56. How do you maintain your mental and physical health as you age?
57. How do you cope with loneliness or isolation?
58. How do you maintain a sense of purpose or relevance as you age?
59. What are your thoughts on giving back or contributing to society?
60. What have you learned about handling grief and loss?
61. What does contentment look like to you?
62. What was a time when you took a significant risk? What was the outcome?
63. How do you maintain humility?
64. What have been the most significant influences on your personal development?
65. Can you share a moment when you experienced a profound sense of peace or tranquility?
66. What is your philosophy towards handling pain or suffering?
67. How do you deal with the concept of mortality?
68. Can you share a profound life lesson you learned from an unexpected source or experience?
69. What is your biggest fear, and how do you confront it?
70. How do you express and manage anger or other strong emotions?
71. What role does faith or spirituality play in your life?
72. What’s your understanding of happiness, and how do you strive to attain it?
73. What do you believe is the role of humor and laughter in life?
74. How important is it for a person to have a hobby or passion? How has yours enriched your life?
75. What is your perspective on the importance of nature and the outdoors?
76. What are your thoughts on the concept of patience?
77. How do you handle situations or people who test your patience?
78. Can you share a moment in your life when you felt a profound sense of wonder or awe?
79. How do you deal with regrets and what could have been?
80. How do you confront and overcome bias or prejudice, either in yourself or in others?
81. What do you believe is the key to maintaining lifelong friendships?
82. How do you approach the process of forgiveness, both for yourself and for others?
83. What have you learned about the importance of honesty and authenticity?
84. How do you deal with disappointment?
85. What is your perspective on the role of kindness in our lives?
86. How do you define personal courage? Can you share a time when you had to be courageous?
87. How do you maintain a sense of adventure or curiosity as you age?
88. How do you balance personal fulfillment with responsibilities and obligations?
89. What are your thoughts on the role of vulnerability in personal growth?
90. How have you managed to adapt to the technological advancements that have occurred over your lifetime?
91. How do you maintain your identity while also changing and evolving over time?
92. How do you define personal integrity, and why is it important?
93. Can you share a moment that restored your faith in humanity?
94. What role does culture and heritage play in your life?
95. What are your thoughts on the concept of simplicity in life?
96. How do you cultivate a sense of wonder in your daily life?
97. Can you share an experience where you deeply connected with another living creature (like a pet)?
98. What are your thoughts on the balance between giving and receiving?
99. How do you deal with the changing dynamics of family relationships as you age?
100. How has your perspective on your own wisdom changed over time?
101. What is your memory of your favorite song and when and how did you listen to it?
102. How do you define love?
103. What did you do after you went through your darkest moments, and what made you decide to go on?
104. What was the kindest thing someone did for you?
105. What was a moment in your life where you learned a specific value or values that you subscribed to for the rest of your life?
106. How do you embrace peace and harmony in your life?
107. What memory do you hold dearest to life every day?
108. What is a habit you would want to teach any person, and why?
109. How do you listen, interpret, and deal with experiences that seem out of the ordinary?
110. How have you dealt with the trauma of others and any trauma you might have experienced?
111. What coping methods have helped make your life better?
112. How do you define love, and what is important about love to you?
113. How do you find inspiration in your daily life?
114. Can you share a time when you overcame a fear or limitation?
115. What are your thoughts on the power of gratitude in shaping one’s perspective?
116. How do you find meaning in the mundane aspects of life?
117. Can you describe a time when you had to make a sacrifice for something or someone you believed in?
118. How do you approach decision-making when faced with multiple options?
119. Can you share a transformative travel experience that broadened your horizons?
120. What role do community and social connections play in your life?
121. How do you handle regret or missed opportunities?
122. Can you share an experience where you had to step out of your comfort zone and what you gained from it?
123. How do you navigate and embrace the ever-changing nature of relationships?
124. What do you believe is the key to maintaining a healthy work-life balance?
125. How do you practice self-care and prioritize your well-being?
126. Can you describe a time when you had to set boundaries for yourself or others?
127. How do you approach the concept of self-discovery and personal identity?
128. What is your perspective on the power of kindness in making a difference in the world?
129. Can you share a moment when you experienced a profound sense of awe in nature?
130. How do you overcome self-doubt and cultivate self-confidence?
131. What is your philosophy on living a purpose-driven life?
132. Can you share a time when you learned an important lesson from a mistake or failure?
133. How do you navigate the complexities of modern technology and its impact on society?
134. What is your approach to maintaining healthy boundaries in relationships?
135. Can you describe a time when you had to let go of something or someone, and what it taught you?
136. How do you foster a sense of belonging in your community or social circles?
137. What is your perspective on the concept of fate or destiny?
138. Can you share an experience where you witnessed or were part of a significant act of kindness?
139. How do you handle change and adapt to new circumstances?
140. What strategies do you employ to manage and overcome stress in your life?
141. Can you share a moment when you felt a deep sense of connection to a larger purpose or higher power?
142. How do you prioritize and pursue your passions in life?
143. What role do rituals or daily habits play in your overall well-being?
144. Can you describe a time when you had to challenge societal norms or expectations?
145. How do you stay open-minded and receptive to new ideas and perspectives?
146. What is your approach to resolving conflicts in relationships or within a team?
147. Can you share an experience where you witnessed or received an act of forgiveness that deeply impacted you?
148. What are 10 things that made you cry?
149. How do you find meaning and purpose in your daily work or profession?150. Can you share a time when you had to make a difficult sacrifice for the greater good?
151. How do you approach and learn from your mistakes?
152. What strategies do you use to overcome self-limiting beliefs?
153. Can you describe a time when you had to adapt to a new culture or environment?
154. How do you foster resilience and bounce back from challenging situations?
155. What role does self-reflection play in your personal growth and development?
156. Can you share an experience where you were able to transform a negative situation into a positive one?
157. How do you find inspiration and motivation during times of stagnation or lack of progress?
158. What are your thoughts on the importance of lifelong friendships and maintaining connections over time?
159. How do you navigate and embrace the process of aging with grace and acceptance?
160. Can you describe a time when you were able to make a positive impact on someone else’s life?
161. How do you approach and learn from constructive criticism?
162. What is your perspective on the balance between ambition and contentment?
163. Can you share an experience that taught you the importance of self-care and well-being?
164. How do you cultivate a sense of inner peace and tranquility amidst a chaotic world?
165. What role does trust play in your relationships, and how do you build and maintain it?
166. How do you approach and resolve conflicts in a compassionate and empathetic manner?
167. Can you describe a time when you had to step out of your comfort zone to pursue personal growth?
168. How do you stay curious and continue learning throughout your life?
169. What are your thoughts on the concept of self-love and its impact on overall well-being?
170. How do you find balance between pursuing personal goals and supporting the needs of others?
171. Can you share an experience that taught you the importance of resilience and adaptability?
172. How do you maintain a sense of optimism and hope during challenging times?
173. What role does self-expression play in your life, and how do you nurture it?
174. How do you approach and manage your finances in a responsible and fulfilling way?
175. Can you describe a time when you had to make a significant change or transition in your life?
176. How do you define and practice empathy in your interactions with others?
177. What are your thoughts on the concept of “finding yourself” and personal identity?
178. How do you maintain a healthy work-life balance in a fast-paced world?
179. Can you share an experience that taught you the importance of embracing diversity and inclusivity?
180. How do you approach and overcome the fear of failure or taking risks?
181. What role does community service or giving back play in your life, and why is it important to you?
182. How do you find joy and cultivate a sense of playfulness in your daily life?
183. Can you describe a time when you had to let go of control and embrace surrender or acceptance?
184. How do you navigate and overcome feelings of self-doubt or imposter syndrome?
185. What are your thoughts on the concept of time and how it shapes our lives?
186. How do you foster and maintain a sense of wonder and curiosity about the world around you?
187. Can you share an experience that taught you the importance of setting healthy boundaries?
188. How do you approach and overcome feelings of loneliness or isolation?
189. What role does self-compassion play in your overall well-being?
190. How do you approach and resolve ethical dilemmas in your personal or professional life?
191. Who was your first hero?
192. How do you cultivate and maintain a positive mindset in challenging situations?
193. Can you share an experience that taught you the importance of self-acceptance and embracing your authentic self?
194. How do you approach and overcome the fear of judgment or criticism from others?
195. What role does self-care play in your overall well-being, and how do you prioritize it?
196. How do you find inspiration and stay creative in your personal or professional endeavors?
197. Can you describe a time when you had to stand up for what you believe in, even in the face of opposition?
198. How do you approach and learn from interpersonal conflicts in your relationships?
199. What are your thoughts on the concept of gratitude and its impact on happiness and fulfillment?
200. How do you stay grounded and connected to your values and beliefs in a constantly changing world?
201. Can you share an experience that taught you the importance of self-education and continuous learning?
202. How do you approach and overcome feelings of self-doubt or imposter syndrome?
203. What role does self-reflection play in your personal growth and development?
204. How do you navigate and embrace the process of aging with grace and acceptance?
205. Can you describe a time when you were able to make a positive impact on someone else’s life?
206. How do you approach and learn from constructive criticism?
207. What is your perspective on the balance between ambition and contentment?
208. Can you share an experience that taught you the importance of self-care and well-being?
209. How do you cultivate a sense of inner peace and tranquility amidst a chaotic world?
210. What role does trust play in your relationships, and how do you build and maintain it?
211. How do you approach and resolve conflicts in a compassionate and empathetic manner?
212. Can you describe a time when you had to step out of your comfort zone to pursue personal growth?
213. How do you stay curious and continue learning throughout your life?
214. What are your thoughts on the concept of self-love and its impact on overall well-being?
215. How do you find balance between pursuing personal goals and supporting the needs of others?
216. Can you share an experience that taught you the importance of resilience and adaptability?
217. How do you maintain a sense of optimism and hope during challenging times?
218. What role does self-expression play in your life, and how do you nurture it?
219. How do you approach and manage your finances in a responsible and fulfilling way?
220. Can you describe a time when you had to make a significant change or transition in your life?
221. How do you define and practice empathy in your interactions with others?
222. What are your thoughts on the concept of “finding yourself” and personal identity?
223. How do you maintain a healthy work-life balance in a fast-paced world?
224. Can you share an experience that taught you the importance of embracing diversity and inclusivity?
225. How do you approach and overcome the fear of failure or taking risks?
226. What role does community service or giving back play in your life, and why is it important to you?
227. How do you find joy and cultivate a sense of playfulness in your daily life?
228. Can you describe a time when you had to let go of control and embrace surrender or acceptance?
229. How do you navigate and overcome feelings of self-doubt or imposter syndrome?
230. What are your thoughts on the concept of time and how it shapes our lives?
231. How do you foster and maintain a sense of wonder and curiosity about the world around you?
232. Can you share an experience that taught you the importance of setting healthy boundaries?
233. When did you realize you would not live forever?
234. How do you approach and overcome feelings of self-doubt or imposter syndrome?
235. What role does self-reflection play in your personal growth and development?
236. How do you navigate and embrace the process of aging with grace and acceptance?
237. Can you describe a time when you were able to make a positive impact on someone else’s life?
238. How do you approach and learn from constructive criticism?
239. What is your perspective on the balance between ambition and contentment?
240. Can you share an experience that taught you the importance of self-care and well-being?
241. How do you cultivate a sense of inner peace and tranquility amidst a chaotic world?
242. What role does trust play in your relationships, and how do you build and maintain it?
243. How do you approach and resolve conflicts in a compassionate and empathetic manner?
244. Can you describe a time when you had to step out of your comfort zone to pursue personal growth?
245. How do you stay curious and continue learning throughout your life?
246. What are your thoughts on the concept of self-love and its impact on overall well-being?
247. How do you find balance between pursuing personal goals and supporting the needs of others?
248. Can you share an experience that taught you the importance of resilience and adaptability?
249. How do you maintain a sense of optimism and hope during challenging times?
250. What role does self-expression play in your life, and how do you nurture it?
251. How do you approach and manage your finances in a responsible and fulfilling way?
252. Can you describe a time when you had to make a significant change or transition in your life?
253. How do you define and practice empathy in your interactions with others?
254. What are your thoughts on the concept of “finding yourself” and personal identity?
255. How do you maintain a healthy work-life balance in a fast-paced world?
256. Can you share an experience that taught you the importance of embracing diversity and inclusivity?
257. How do you approach and overcome the fear of failure or taking risks?
258. What role does community service or giving back play in your life, and why is it important to you?
259. How do you find joy and cultivate a sense of playfulness in your daily life?
260. Can you describe a time when you had to let go of control and embrace surrender or acceptance?
261. How do you navigate and overcome feelings of self-doubt or imposter syndrome?
262. What are your thoughts on the concept of time and how it shapes our lives?
263. How do you foster and maintain a sense of wonder and curiosity about the world around you?
264. Can you share an experience that taught you the importance of setting healthy boundaries?
265. How do you approach and navigate through periods of uncertainty in your life?
266. What role does intuition play in your decision-making process?
267. How do you cultivate a sense of gratitude and appreciation in your daily life?
268. Can you describe a time when you had to let go of a grudge or resentment and how it affected you?
269. How do you approach and overcome fear or anxiety in pursuit of your goals?
270. What role does honesty and authenticity play in your relationships and interactions with others?
271. How do you maintain a sense of wonder and awe in the face of life’s challenges?
272. Can you share an experience that taught you the importance of embracing change and adaptability?
273. How do you approach and overcome feelings of loneliness or isolation?
274. What are your thoughts on the concept of self-forgiveness and its impact on personal growth?
275. How do you stay true to your values and beliefs in a world that often challenges you?
276. When did you, if ever believe in God?
278. What is your concept of a mature and psychologically healthy person? What are his/her characteristics, values and behaviors? (question posed in the 1969s by Prof. Clare Graves to his students)
279. What are the most important mental models, frameworks or theories that shaped your thinking?
280. How do you look at pain and what role and influence did it have in your life?
281. What do you expect to happen after you die?
282. What do you want your children to know before you die?
50 questions to help you reflect on your career and capture your professional wisdom:
1. How did you choose your career path?
2. What was your first job and what did you learn from it?
3. What was the most difficult decision you’ve made in your career?
4. What’s the best career advice you’ve ever received?
5. Who has been your most influential mentor and why?
6. How have you handled work-life balance throughout your career?
7. What accomplishment in your career are you most proud of?
8. How did you handle setbacks or failures?
9. What’s the most significant risk you’ve taken in your career?
10. How have you navigated workplace politics?
11. What skills have been most valuable in your career?
12. How have you handled criticism at work?
13. How did you continue learning and developing professionally?
14. How have you developed leadership skills throughout your career?
15. What’s the most difficult feedback you’ve ever received and how did you respond?
16. How have you advocated for yourself in the workplace?
17. How did you build a professional network?
18. What strategies have you used to manage stress and burnout?
19. How have you handled conflicts with colleagues or superiors?
20. How have you adapted to changes in your industry?
21. How did you determine when it was time to change jobs or roles?
22. How have you contributed to your company’s culture and values?
23. How did you approach problem-solving in your work?
24. How did you identify and pursue career advancement opportunities?
25. How did you mentor or support others in their career journeys?
26. How have you navigated major transitions in your career?
27. What strategies have you used to stay organized and productive?
28. What is the most valuable lesson you learned from a mistake you made at work?
29. How did you build strong relationships with clients or customers?
30. What role has diversity and inclusion played in your career?
31. How did you handle ethical dilemmas in your work?
32. How have you used technology to improve your productivity or job performance?
33. How did you stay motivated when work was challenging or tedious?
34. What are the most important qualities for success in your field?
35. How did you navigate the balance between personal satisfaction and financial needs in your career?
36. How have you developed your communication skills for your professional life?
37. How did you approach negotiations in your career, such as salary or project resources?
38. What was the toughest team you had to work with and how did you handle it?
39. How have you demonstrated resilience in your career?
40. What are the key industry trends you have had to adapt to over your career?
41. How did you ensure that your work was aligned with your company’s goals and objectives?
42. What innovative ideas or practices have you introduced in your work?
43. How have you learned from your direct reports or junior team members?
44. How have you managed a team through a crisis or major change?
45. How have you dealt with imposter syndrome, if you’ve experienced it?
46. How have you handled situations where you felt underqualified or out of your depth?
47. How have you responded when you didn’t get a role or promotion you wanted?
48. What do you wish you had known at the beginning of your career?
49. How have you handled job insecurity or market downturns in your industry?
50. What advice would you give someone starting in your profession today?
