self improvement tips

101 Thought Provoking Questions to Ask Yourself Before It’s Too Late

This is your chance to live the life you wish you had.

You could close down this article right now, pretend that you never saw it, and go on living your life as usual – but when do you plan on challenging yourself to live an even ‘bigger’, more meaningful, more fulfilling and deeper life?

You see, many of us live our lives on autopilot.

We are no longer piloting and steering our life and rather, we get into patterned and routined ways of living.

The worst part is – we stop challenging ourselves to live a meaningful life – and we ‘settle’ for a comfortable life.

If you feel that you are living on autopilot, then perhaps it’s time you asked yourself a few important questions.

We often avoid asking ourselves ‘thought provoking’ questions because they could potentially push us out of our comfort zone.

Once you become aware of the things in your life that require change – you become conflicted and can no longer pretend that everything is fine the way it is.

The good news is that it’s never too late to change the direction of your life, to do something meaningful and to feel completely fulfilled in life.

These 101 thought provoking questions are the first step to realizing what you need to change and do differently in your life.

Make sure you really dig deep and don’t avoid difficult or conflicting emotions – these are necessary to provoke the much needed change in your life.

1. Do you like who you are?

2. What would people say about you at your funeral?

3. What would you regret not doing in your life?

4. What’s the wisest thing you have ever heard someone say?

5. What lessons in life did you learn to hard way?

6. How often do your biggest worries and fears come true?

7. If you had one year left to live, what would you try to achieve?

8. Do you serve money or does money serve you?

9. Are you afraid of being your true self around others? Why?

10. What are you grateful for?

11. Have you done anything you are proud of lately?

12. Have you made any recent acts of kindness?

13. If you knew that you would die tomorrow, what questions would you ask yourself?

14. If your biggest fears came true, would it matter in five years from now?

15. How would you describe yourself?

16. Do you take people’s advice?

17. Do you get quickly offended?

18. Do you consider yourself to be a likable person?

19. ‘We make a living by what we get, we make a life by what we give’ – What does this mean to you?

20. Are you enriching the lives of others?

21. Are you living a meaningful life?

22. What makes a meaningful life?

23. Would you ever give up your life to save another?

24. How much would you be willing to sacrifice for people in poverty?

25. If you could live one day over and over again, what would you choose to do?

26. Do you think you are important and worthy of affection and love?

27. What would make you feel more worthy? What do you believe needs to be different about you?

28. What brings you down the most often?

29. Would you rather work less (and do the things you enjoy) and have less money?

30. Where do you find peace?

31. What is the most important quality you look for in another person?

32. What is your biggest dream in life?

33. What is your biggest fear?

34. How would the world be different if you had never been born?

35. What life lessons do you wish you knew 10 years ago?

36. If you could tell your younger self one thing, what would it be?

37. If your life was a movie, what would the title be?

38. If your life was a movie, would you enjoy watching it?

39. What does success mean to you?

40. If you could be a different person, who would you be?

41. What was the best day of your life? Why?

42. What do you look forward to most in life?

43. What bad habits do you want to ditch?

44. Who do you look up to and why?

45. Do you know your partners love language?

46. Do the people you love most know how much you love them?

47. Are you satisfied with the depth of your relationships?

48. What do you owe yourself?

49. Based on your current day-to-day life, what do you expect to achieve in 5 years from now?

50. Do you say ‘yes’ too often when you really want to say ‘no’? Why?

51. What did you learn yesterday?

52. What do you like about yourself?

53. Would you consider yourself to be a generous person?

54. Do you really listen when people talk to you?

55. What is the number one change you need to make in your life this year?

56. How many hours per week do you spend on the internet?

57. What are your most common negative thoughts? Are they logical?

58. Do you think it’s too late to do certain things in your life? Why?

59. If you could be the most influential person in the world, what would you change?

60. How much time do you spend with your family and friends?

61. Where do you want to be in 5 years from now?

62. Is your life complicated by unnecessary things?

63. How can you simplify your life and focus on the most important things to you?

64. What stresses you out?

65. What makes life easier?

66. How often do you give without expecting anything in return?

67. What is your greatest challenge?

68. What is most important to you in life? Are you giving it the time it deserves?

69. If you could send a message to the world, what would you say in 30 seconds?

70. What do you most regret never telling someone?

71. When was the last time you tried something new?

72. Are you afraid to speak your own opinion?

73. Do you give into others too often and feel resentful because of it?

74. Are you holding onto something that you need to put behind you?

75. How often do you let your fears hold you back?

76. Do the people in your life bring the best out of you?

77. How often do you make excuses?

78. What is one mistake that you will never do again?

79. Which is worse, failing or never giving it a shot?

80. What has grown you the most as a person – your challenges and trials or the comfortable yet enjoyable moments in life?

81. If you could choose to have no more challenges or obstacles in life, would you?

82. In one word, what is standing between you and your biggest goal?

83. How often do you go to bed feeling angry?

84. Would it be wrong to steal in order to feed a starving child?

85. If you paid more attention to the sad things in this world, would you feel more conflicted about it?

86. If we learn from our failures, then why is it so bad to fail?

87. What could you pay more attention to in life?

88. Why do we think of others the most when they’re no longer around?

89. What does it look like to make the most of your life?

90. What have you given up on?

91. How many people do you truly love and what are you doing for them?

92. Do you ask enough questions, or are you happy to settle for what you already know?

93. What were you doing when you last lost track of time?

94. Do you think you would be happy if you never had to work again?

95. How old would you be if you didn’t know how old you are?

96. If you could ask for one wish, what would it be?

97. What inspires you in life?

98. What can you not live without the most?

99. What do you enjoy doing over and over again?

100. When did you last laugh so much it hurt?

101. What is stopping you from living the life you want to live?

Hopefully after reading these questions, your mind is going absolutely crazy with all sorts of thoughts and ideas.

That’s what you want!

By taking the time and effort to ask yourself these questions (and answer them), you will most certainly be able to find more depth to your life.

If we always avoided questions that provoke change in our lives, we would stay in the same place! We wouldn’t move forward and find deeper meaning and fulfillment, but rather feel rather empty inside.

Just remember – We only live life once but if we do it right, once is enough.

So I challenge you….make the most of all your precious moments in life.

Once their gone, you can never get them back.

Push yourself further and ask yourself all sorts of thought provoking questions so that you can live a rich, meaningful and fulfilling life!

About the Author: Chantalle Blikman is a writer and co-founder of Want2discover. Visit her website for more great articles on self-improvement and how to live a fulfilling and meaningful life. Be sure to download a copy of her Free Ebook: 52 Simple Steps Towards Happiness and Success.


Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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