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99+ Thought Provoking Questions to Ask & Answer Today

Dan Western



99+ Thought Provoking Questions to Ask & Answer Today

What are thought provoking questions?

The meaning of these questions is to get you think deeply about your answers, and the effects they’re having on your life. Thought provoking questions help you to become more self-reflective, and therefore be able to improve your life in multiple areas.

It’s probably best to write your answers down, so that you can look back on them at a later time and analyze whether the question has helped you to think differently.

Here are 99+ thought provoking questions that you can ask and answer yourself today:


99+ Thought Provoking Questions

1. Are you able to say no, even when it makes you unpopular?
2. Are you satisfied with your work?
3. Do you bring your work home with you?
4. Do you follow through on commitments?
5. How do you apply the learning from this regret to your actions today?
6. How do you react when you encounter a homeless person?
7. How much time are you spending on social media?
8. If you could ask for one wish, what would it be?
9. If you could spend 10 minutes with anyone, living or dead, who would it be? Why?
10. If you had a year left to live, what would you achieve over the next 12 months?
11. If your entire life was a movie, what title would best fit?
12. What are you looking forward to?
13. What did your life teach you yesterday?
14. What gives you meaning?
15. What have you done today to make someone’s life better?
16. What is the source of your procrastination?
17. What small habit can you change today?
18. What would happen if you never wasted another minute of your life, what would that look like?
19. When it’s all said and done, will you have said more than you have done?
20. When you think of your home, what immediately comes to mind?
21. Who are you becoming?
22. Would you break the law to save a loved one?
23. Are you content? If not, what is the source of your lack of contentment?
24. Are your goals and dreams written down?


Thought Provoking Questions (25-49)

25. Do you choose happiness or leave it to chance?
26. Do you have a personal mission statement?
27. How do you challenge your assumptions?
28. How do you spend the majority of your free time? Why?
29. How often do you keep in touch with family and friends?
30. If you could eliminate one things from your life today, what would it be?
31. If you could start over, what would you do differently?
32. If you had to teach someone one thing, what would you teach?
33. Name one psychological barrier in your life? What is it holding you back from doing?
34. What are you spending your money on?
35. What do you really love to do? Do you do it often? If you answer no, why not?
36. What gives you peace?
37. What have you given up on?
38. What is your favorite quote?
39. What step can you take today in order to fulfill your deepest desire?
40. What would you change about your life if you knew you would never die?
41. When someone sees your name on caller ID, what thoughts and feelings do you want them to have?
42. Where would you like to live? Why haven’t you moved?
43. Who are you really? Describe yourself without using your name, or any attributes given to you by society and really think. Deep down, who are you?
44. Would your life be better or worse, if you knew the time and place where you would die?
45. Are you feeding your fears or your hopes and dreams?
46. Did you pause to celebrate the last time you accomplished a goal, big or small?
47. Do you consider yourself the hero or the villain in your story?
48. Do you meditate daily for at least 5 minutes?
49. How do you deal with failure?

Related:  8 Inspirational Role Models to Look Up to


Thought Provoking Questions (50-74)

50. How many people do you truly love? What are you doing for them?
51. How would you describe yourself in 3 words?
52. If you could go back in time, once, and change a single thing – what would it be?
53. If you could watch everything that happened in your life until now, would you enjoy it?
54. If you had unlimited resources, how would you live your life?
55. Standing at the gates of heaven, and God asks you “Why should I let you in?” What do you reply?
56. What can you do today that you couldn’t do a year ago? What will you be able to do at this time next year?
57. What do you want most out of life?
58. What habits are holding you back from success?
59. What is the biggest frustration you’re facing now?
60. What is your greatest strength?
61. What story are you telling yourself about your life?
62. What would you do differently if you knew that no one was judging you?
63. When was the last time you had an exciting idea that kept you awake most of the night? Are you pursuing that idea today?
64. Which bad habits do you want to break?
65. Who are your professors in the school of life?
66. Are you holding onto something that you need to let go of? What’s stopping you?
67. Did you say “I love you” to the most important person in your life today?
68. Do you consider yourself worthy of love and admiration?
69. Do you trust your own instincts?
70. How do you express your gratitude for good things and people you have in your life?
71. How many times a day do you check your email?
72. If karma was coming back to you, would it help or hurt you?
73. If you could only speak one word today, what would you say?
74. If you dropped everything to pursue your dreams, what would you be risking?

Related:  Top 20 Best Personal Development Authors of All Time


Thought Provoking Questions (75-99)

75. If you received enough money to never need to work again, what would you spend your time doing?
76. What are the chances you’ve passed up on that you regret?
77. What did failure to reach your goal teach you about yourself?
78. What do you want your life to look like in 5 years? Do you have a plan to get there?
79. What have you done that you’re most proud to have achieved?
80. What is the difference between living and existing?
81. What is your greatest weakness?
82. What terrifies you the most?
83. When did you last push the boundaries of your comfort zone?
84. When was the last time you travelled somewhere new?
85. Which books have influenced you the most?
86. Whose life have you had the greatest impact on?
87. Are you open to experiencing something outside your comfort zone everyday?
88. Do you ask enough questions, or are you happily settling for what you know already?
89. Do you fear rejection? What are you doing to overcome this fear?
90. Have you ever invested in yourself financially? Why or why not?
91. How do you keep a sense of perspective when life gets difficult?
92. How much control do you really have over yourself?
93. If today was the last day of your life, what would you want to do?
94. If you could send a message to the entire world, what would you say in 30 seconds?
95. If you had a friend that you spoke to the same way you speak to yourself, how long do you think that person would allow you to be your friend?
96. If you were asked to describe yourself in one word, what would it be?
97. What are the things that stand between you and complete happiness?
98. What did you want to be when you were a kid?
99. What gets you excited and driven to achieve?

Related:  6 Great Tips When Dealing With Frustration


Thought Provoking Questions (100-107)

100. What have you done to pursue your dreams lately? How about today?
101. What is the last thing that you’ve done that’s really worth remembering?
102. What makes you smile?
103. What were you doing when you last lost track of the time?
104. When did you not speak up, when you know you really should have?
105. When was the last time you tried something new?
106. Who are the people you surround yourself with?
107. Would you be a martyr and risk your reputation by standing up for what is right in front of your peers? Or is it better to be pragmatic and do nothing?



The questions featured in this article are some of the best thought provoking questions of all time. Forcing you to question you career, your personality, your relationships, your happiness, your true purpose.

Hopefully, they’ll help you to think differently about things, and use that information to improve your life!

Which of these 99+ thought provoking questions impacted you the most? Leave a comment below.

Dan Western is the founder of Wealthy Gorilla. Dan has been running Wealthy Gorilla and studying self-development, personal finance and investment for the last 7 years, whilst traveling the world and being able to call Bali, Indonesia, his HQ. To this day, Wealthy Gorilla has become one of the fastest growing self-development sites in the world; with over 160 million views worldwide, and more than 200,000 followers on social media. Dan's mission is simply, to inspire others to live their dreams and be the person to whom they say; "Because of you, I never gave up."

1 Comment

1 Comment

  1. Sim Campbell

    Jan 6, 2017 at 2:07 am

    These are definitely some great questions, Dan.

    I think the best way to tackle these would be to actually WRITE THEM DOWN and as well as the answer. Don’t just think about it, write. Writing causes you to be introspective and thoughtful, allowing you to further hone in on answers to how to live your best life.

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