101 Important Questions To Ask Yourself

Question mark on sand

“The key to wisdom is knowing all the right questions.” – John Simone

What questions do you ask yourself every day?

Believe it or not, the kind of questions you ask determine the kind of life you lead. That’s because your questions trigger its own set of answers, which lead to certain emotions, which then lead to certain actions (or inactions), followed by results. If you ask yourself limiting questions, you’ll get limited results. If you ask yourself mind-opening, forwarding questions, you’ll gain a lot more out of them.

Some people like to ask questions like “Why am I so unlucky?”, “What if I had done this earlier?” and “Why am I always in such a situation?”. Because these questions are backward looking, the answers you get with them are naturally disempowering. On the other hand, questions like “What can I learn from this experience?”, “What can I do differently move forward?” and “What am I grateful for?” are empowering. They provoke you and get you thinking, putting you on the path to a better life.

If you’re someone who normally doesn’t self-reflect, you might be stumped by questions. However, this is perfectly normal. I remember when I was a small primary school student, the teacher asked us how we would describe ourselves. The question got me stumped, because I had never thought much about it. It took me some time to find some meaningful adjectives to describe myself, but even then they didn’t seem right. That was one of the starting points of my self-exploration journey. Somewhere along the way, I became a big fan of introspection, enjoying the process of self-reflecting and thinking over questions.

Today, I believe questions are a key to self-awareness and personal growth. In my 1-1 coaching sessions, I enable my clients to discover the answers to their goals/questions by asking them the right questions. It’d be easy if I just tell my coachees what they “should” do and what they “should not” do. But that’s not the point. It’s about empowering my clients to discover themselves through asking the right guiding questions, catered to their situation and their profiles. The right questions will help them untangle the blockages in them and connect with their inner self.

It doesn’t matter if you get stumped in the beginning, or if you don’t know the answers to the questions at first. Our minds are boundless. Just because you don’t get an answer immediately, it doesn’t mean there are no answers. The answers are there — it’s just that your mind is too foggy since you’ve not consulted it before. The more you ask, the clearer your mind will be, and the more ready you’ll be to receive the answers.

Here are 101 important questions for your self-reflection, by yours truly. Many are questions that I ask my 1-1 clients during our coaching sessions to help them uncover their inner self. These questions will help you focus on what’s important to you, and what you want. They are not meant to be answered all at one shot — they are to be reflected duly over time, as part of your growth journey. Pick out a few questions to reflect on today, then bookmark and check back a week later to think over the others. Check back regularly to reflect on the questions.

Remember, there is no one final answer. It’s a continuous discovery process. Your answers to the questions today will be different from your answers one month, three months, six months, and one year down the road. Add these important questions to your weekly review sessions. This is a highly important article for your growth journey.

Here they are:

  1. Who are you?
  2. What are you passionate about?
  3. What are the achievements you are most proud of?
  4. What are you most grateful for in life? (Day 14 of Live a Better Life in 30 Days Program is about expressing gratitude.)
  5. What are the most important things to you in life?
  6. How would you describe yourself?
  7. What are your values? What do you represent? What do you want to embody? (On Day 15 of Live a Better Life in 30 Days Program, you will identify your values.)


  8. Do you love yourself?
  9. … Why or Why not?
  10. How can you love yourself more today?
  11. What is your ideal self? What does it mean to be your highest self?
  12. Look at your life now. Are you living the life of your dreams?
  13. If you have one year left to live, what would you do?
  14. If you have one month left to live, what would you do?
  15. If you have one week left to live, what would you do?
  16. If you have one day left to live, what would you do?
  17. If you have an hour left to live, what would you do?
  18. If you have one minute left to live, what would you do?


  19. What would you do today if there is no more tomorrow?
  20. What are the biggest things you’ve learned in life to date?
  21. What advice would you give to yourself 3 years ago?


  22. If you are yourself 1 year from the future, how would you advise the you now? (On Day 22 of Live a Better Life in 30 Days Program, we travel to the future to give advice to the us today.)
  23. Is there something you’re still holding on to? Is it time to let it go?
  24. What are you busy with today? Will this matter 1 year from now? 3 years? 5 years?
  25. What are your Quadrant 2 tasks?
  26. What opportunities are you looking for?
  27. How can you create these opportunities?
  28. What are your biggest goals and dreams?
  29. What’s stopping you from pursuing them? …Why? How can you overcome them?
  30. If you are to do something for free for the rest of your life, what would you want to do?
  31. What would you do if you cannot fail; if there are no limitations in money, resources, time or networks?

    Girl with balloons

  32. What do you want to achieve 1 year from now?
  33. … 3 years?
  34. … 5 years?
  35. … 10 years?
  36. How important are these goals to you?
  37. What if these goals are doubled? Tripled? Magnified by 10? How would you feel? Would you prefer to achieve these or your previous goals?
  38. Who are the people who have achieved similar goals? … What can you learn from them?
  39. Are you putting any parts of your life on hold? … Why?
  40. What’s the top priority in your life right now?
  41. What are you doing about it?
  42. If you were to die tomorrow, what would be your biggest regret? What can you do now to make sure that doesn’t happen?
  43. For every experience you get: What are the biggest things you have learned?
  44. How can you do this better the next time?
  45. If you have 1 million dollars, what will you do with it?

    Money notes

  46. Do you love your job?
  47. What is your ideal career?
  48. How can you start creating your ideal career starting today?
  49. What is your ideal diet?
  50. What do you need to do to achieve your ideal diet?
  51. What is your ideal home like?
  52. What do you need to do to achieve your ideal home?
  53. What is your ideal physical look?
  54. What do you need to do to achieve your ideal physical look?
  55. What is your ideal life?
  56. What can you do to start living your ideal life?
  57. What would you want to say to yourself 1 year in the future?
  58. … 3 years?
  59. … 5 years?
  60. … 10 years?Birthday
  61. What do you fear most in life?
  62. Is there anything you are running away from?
  63. Are you settling for less than what you are worth? … Why?
  64. What is your inner dialogue like? (Day 26 of Be a Better Me in 30 Days Program is about uncovering your limiting thoughts.)
  65. What limiting beliefs are you holding on to?
  66. Are they helping you achieve your goals?
  67. If not, is it time to let them go?
  68. What empowering beliefs can you take on to help you achieve your goals?
  69. What bad habits do you want to break?
  70. What good habits do you want to cultivate?
  71. What are the biggest actions you can take now to create the biggest results in your life?
  72. Where are you living right now – the past, future or present?
  73. Are you living your life to the fullest right now?
  74. What is the meaning of life?
  75. What is your purpose in life? Why do you exist? What is your mission?


  76. How can you make your life more meaningful, starting today?
  77. What drives you?
  78. What are the times you are most inspired, most motivated, most charged up?
  79. What did you do during those times? How can you do more of that starting today?
  80. How can you change someone’s life for the better today?
  81. Who are the 5 people you spend the most time with?
  82. Are these people enabling you or holding you back?

    Reading book on a field

  83. What qualities do you want to embody? (Refer to Q7: Values and Q11: Ideal Self) Where can you meet people who embody these qualities?
  84. Who inspire you the most?
  85. How can you be like them?
  86. What is your ideal life partner like?
  87. Where can you find him/her?
  88. How can you get to know him/her?
  89. Are you afraid of letting others get close to you?
  90. … Why?


  91. Who is/are the most important person(s) to you in the world?
  92. Are you giving them the attention you want to give?
  93. How can you spend more time with them starting today?
  94. What kind of person do you enjoy spending time with?
  95. How can you be this person to others?
  96. Who do you want to be like in 1 year?
  97. … 3 years?
  98. … 5 years?
  99. … 10 years?
  100. Who are your mentors in life? (formal or informal)
  101. What is one thing you’re going to do differently after reading this article?
Get the manifesto version of this article: The Self-Reflection Manifesto

Other Articles in the 101 Series

If you like this post, you’ll love the other posts in the 101 series:

  1. 101 Things To Do Before You Die
  2. 101 Most Inspiring Quotes of All TimeVol 1 | Vol 2 | Vol 3 | Vol 4
  3. 101 Ways To Live Life To The Fullest
  4. 101 Important Life Principles To Live By Every Day
  5. 101 Ways To Be a Better Person

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This is part of the Inspiration & Motivation series. Check out the other articles in the series:

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