143 Questions To Ask Yourself Before You Die

This is a piece I wrote for a personal development podcast which isn’t online any more called “Go Legendary”. I thought it might fit here — thanks for reading.

Sometimes, We All Need A Kick In The Butt.

This list was designed to do just that.

Grab a sheet of paper, read through the list, and write down the first answer that comes to mind. You’ll need to think about some more than others, but if you can get through all 143 of them, you’ll have packed more introspection into one session than most people do in a year–or maybe their entire lives.

Ready… set… go!

What I Know About Me and The World

1. who am I?
2. what do I know to be true?
3. what are three of my best qualities according to me?
4. what are three of my best qualities according to my best friend?
5. what are three of my best qualities according to my significant other (or ex)?
6. what are my three worst qualities?
7. who is my best friend?
8. what excuses have I been telling myself to keep me from action?
9. what does my name mean?
10. was I named after anyone?
11. when was the last time I did something for the first time?
12. who was my childhood hero?
13. what three words describe my current first impression?
14. what three words describe my ideal first impression?
15. when i’m wasting time, what do I like doing?
16. i need to calm myself down. what do I do?
17. i need to pump myself up. what do I do?
18. i just woke up. what’s the first thing to cross my mind?
19. what’s my favorite thing to do when i’m by myself?
20. what makes me want to work out/exercise? if I don’t, why not?
21. what, if anything, would I like to be responsible for?
22. do I have any traditions? what are they?
23. what limitations do I think I have?
24. what would be different if I didn’t have them?
25. when I meet a new person, what do I notice about them?

The Story So Far

27. what’s the motto for this era of my life
28. who are the primary characters in my story right now (besides me?)
29. how are they influencing me?
30. how am I influencing them?
31. what do I want more of in my life to make me happy?
32. what do I want less of in my life?
33. when was the last time I lost track of time?
34. what’s the most important thing to focus on right now?
35. what’s my quest in life?
36. what are three things that make me happy?
37. what are three things that i’m grateful for?
38. when was the last time I sang karaoke?
39. when was the last time I helped someone?
40. who has helped me get where I am?
41. what choice do I regret in my life?

What’s Next for Me?

41. where do I want to visit next?
42. what one habit would I like to make?
43. what one habit would I like to break?
44. who would I meet, if I could meet anyone?
45. what sport (extreme or otherwise) would I like to try?
46. what natural wonders do I want to see before I die?
47. what celebrations/festivals/parties do I want to attend?
48. what parties do I want to throw?
49. what will my funeral be like?
50. what’s an adventure that I can have in the next 30 days?
51. what needs to be in my will?
52. do I want to get married? if married, do I want to get divorced?

Your Creative Side

53. if/when I get interviewed on TV, who will do the interview?
54. if/when I get interviewed on TV, what will we talk about?
55. if I were going to build ONE of something, what would it be?
56. if I could invent something to change the world, what would it be?
57. would I rather write a book, tv show, or screenplay?
58. what would this written work be about?
59. what skill/hobby would I like to master in my life?
60. what’s something that I collect, or would like to collect?

The Best In The World

61. what is the best book I’ve ever read?
62. what book should everyone else read?
63. what book have I been wanting to read (but haven’t yet)?
64. what is my favorite photograph?
65. what’s my favorite piece of artwork?
66. what is the best movie ever?
67. what’s a classic movie I haven’t seen but have wanted to?
68. if I could have ONE superpower, what would I choose?
69. if I could become an animal, what would I choose?
70. if I won the lottery, what would I do with my winnings?
71. who is one of my current heroes?
72. if a genie gave I three wishes, what would I ask for?
73. what is the best food ever?
74. what’s one food i’d like to try?
75. what is my favorite color and what does it symbolize?
76. if I were in a musical group, what type of music would I play?
77. what is the best smell in the world?
78. what time of day are I most productive?
79. what time of day are I most useless?
80. what’s my dream job?
81. what do I do better than anyone I know?
82. what are my biggest strengths/assets?
83. what are my hidden talents?

The Darker Side of You

84. have I ever committed a crime?
85. if I were going to plan a heist, what would I steal?
86. what’s the worst thing i’ve ever done for myself?
87. what’s the best thing i’ve ever done for myself?
88. What’s a secret that I’ve never told anyone (about yourself or about someone else)?
89. what has been the saddest moment of my life?
90. what am I afraid of?
91. If I wasn’t afraid of these things, how would my life be different?
92. Am I afraid to die? why?

What If…

93. what is the thing i’re most proud of accomplishing so far?
94. what will I regret doing or not doing if I continue living as I are?
95. what do I want my legacy to be?
96. if I retired today, what would I do?
97. at what age do I plan to retire?
98. given $ : 100, 1000, 10,000, 1mil – what do I do with it?
99. i have to get a tattoo. what and where?
100. what was the best part of being a kid?
101. i have to change my name. what’ll it be?
102. You have to write a letter to someone (that’s right, a real letter.) Who’s it going to? What’ll it say?
103. what would I change about my appearance?
104. if I could tell my past self anything, what would it be?

Deep Questions

105. what parts of my life have become stagnant?
106. what are my most appealing characteristics?
107. am I doing something that matters?
108. what am I doing to help others?
109. what am I afraid of?
110. who do I love, and what am I doing about it?
111. am I taking enough risks?
112. what’s a calculated risk I could take this week?
113. what makes me angry?
114. what was my most fulfilling/content moment?
115. when am I proud of what i’ve done?
116. what grudges am I holding?
117. when do I stand up for myself?
118. what path does my heart say I should follow?
119. do I smile more, or frown more?
120. what did I used to love doing, when I was young?
121. what excites me about the future?
122. where do I want to be tomorrow?
123. what do I look forward to every day?
124. when I daydream, what do I see?

Unlocking Your Passions

125. what subject can I talk about for hours?
126. what do I most enjoy doing for others?
127. what are five experiences that gave me a sense of growth and fulfillment?
128. what makes me smile?
129. what’s easy for me?
130. what sparks my creativity and gets I imagining?
131. what would I do for free?
132. what would I regret not having tried?
133. if I could subscribe to only 5 magazines, what would they be?
134. if I were stranded on a desert island with food, water, and shelter, what would I miss most?
135. what external barriers are holding me back from pursuing my passion?
136. what do people frequently ask I for help with?
137. if I had to teach something, what would I teach?
138. if I were giving a TED talk (18-minute presentation to a young, intelligent and influential audience), what would it be about?
139. what are my values (http://thinksimplenow.com/resources/ThinkSimpleNow-Values.pdf)
140. what challenges have I already overcome?
141. what challenges are I now facing?
142. if I could live in one place for the rest of my life, where and why?
143. what’s on my bucket list (to do before I die)?