When we are not sure of ourselves, we often turn to family, friends, and mentors for advice. We ask them what we should do about our jobs, relationships, opportunities, and dilemmas. We often seek the approval of the majority, and use the opinions of others to make assessments of ourselves.

While we love the people in our lives from whom we seek advice, they are not always objective. In fact, it's pretty hard for anyone to be objective and truly offer great guidance. That's why great mentors and coaches are such game-changers: They help silence the noise of society and unearth your own truth.

I believe it's easier to find your truth than you expect. The answer always lies within us--it just takes some time to excavate. Asking questions is a great way to be more objective about your situation and to discover new things about yourself and the path you want to be on.

These 100 questions will help you understand where you are in your career versus where you want to be and help you to identify actionable steps towards making a powerful vision a reality. Answer them honestly. Step away and then come back and read your answers with a fresh slate. You'll know what you need to do.


  1. What do you like to learn?
  2. What do you do in your spare time for fun?
  3. Do you do certain activities because you think it's what you have to do?
  4. Are you creating a career for your parents, for society, from your own excitement, or for money?
  5. Do you believe that making money will make you happy?
  6. What is your definition of work?
  7. Do you believe that you can love what you do and make money doing it?
  8. What is your dream?
  9. Is that dream realistic?
  10. Do you believe in yourself?
  11. What challenge excites you the most in your life right now?
  12. What impact do you want to have on other people's lives or in the world?
  13. Do you feel confident that you are exceptional at something?
  14. Whom can you count on for support?
  15. Do you believe that with hard work and focus you can do whatever you set your mind to?
  16. Do you think your intelligence is set?
  17. If you think it is, how does that affect your career choices?
  18. If you think it's not, how does that affect your career choices?
  19. Whom do you get career advice from?
  20. Can these people be objective about you? (i.e., are they family or friends?)
  21. When you were in college, what did you envision for yourself and your career?
  22. What do you want: more joy or more power?
  23. Do you want to be like your parents?
  24. Why or why not?
  25. What do you do that builds your confidence?
  26. Can you do that more often?
  27. If you can't, why not?
  28. Do you exercise, eat healthy, and take care of yourself?
  29. If not, why not?
  30. Do you like your job?
  31. Do you feel like you are valued?
  32. Do you trust your superiors and your colleagues?
  33. Do you wake up excited to be working in this job?
  34. If no, why not?
  35. What excites you about the work you are doing?
  36. How often are you bored?
  37. Are you proactive about sharing your ideas with your team and managers?
  38. How would you describe the work culture?
  39. Does that culture work for you?
  40. Do you laugh at work frequently?
  41. Are you inspired by the leaders in the organization?
  42. Do the leaders talk to you?
  43. Are you clear about what the next level is for you at this organization?
  44. Does that excite you?
  45. How important is loving your job to you?
  46. How important is it that people you work with love what they do?
  47. Do you have a career vision?
  48. Do you think of that vision often?
  49. How important is security to you?
  50. Are you willing to take a risk with your career and your comfort zone?
  51. When was the last time you did something that scared you?
  52. Was that exhilarating?
  53. Do you feel fulfilled by your work?
  54. Do you care about being fulfilled?
  55. What is the advantage of being purpose driven, if you are not currently?
  56. Whom do you admire most?
  57. Are they passionate and purpose driven by their work?
  58. Do you think you deserve to have a job you love and get paid well?
  59. Are you confident most of the time?
  60. What is your number-one confidence barrier?
  61. What can you do to work on that barrier?
  62. What is your greatest fear?
  63. What new behavior would help you achieve your goals?
  64. Do you think you are the best at what you do?
  65. Why or why not?
  66. Do you care what other people think of your success?
  67. When you make decisions about your career, do you often consider what other people will think of your decision?
  68. Are you money- or power-driven?
  69. Why or why not?
  70. What advice would you give yourself today about where you are in your career based on where you want to go?
  71. If you are an entrepreneur, have you always believed you were meant to be an entrepreneur?
  72. What is your favorite part of running your own business?
  73. Least favorite?
  74. Are you in your dream job?
  75. If not, do you know what your dream job is?
  76. Do you feel confident most of the time or do you struggle a lot?
  77. Do you enjoy working alone?
  78. How do you do your best thinking?
  79. Where do you do your best thinking?
  80. Do you feel fulfilled by the work you are doing?
  81. If you don't, why not?
  82. Do you give yourself time to think?
  83. Do you feel like you are efficient with your time?
  84. If not, what is your main distraction?
  85. How can you eliminate that distraction?
  86. Do you have a clear vision for yourself and your business?
  87. Is the work you are doing a reflection of your greatest strength?
  88. If not, can you hire someone to support you in doing work that is not in line with your strengths?
  89. What do you think your performance barriers are? What behaviors are holding you back?
  90. Do you have a plan for eliminating the performance barriers?
  91. If no, why not?
  92. If yes, what is it? Can you start that today?
  93. Are you pushing your comfort zone at least once a week?
  94. What can you do to ensure you are getting out of your comfort zone more regularly?
  95. Do you feel successful?
  96. What does success mean to you?
  97. What is driving you?
  98. Do you use that driving force in your business?
  99. If you don't, how can you bring more of that to your daily work-life?
  100. What have you learned about yourself and your status by answering the above questions?