top of page

Challenge Yourself - 100 Must Ask Questions to Create Your Best Ever You

Most of us would rather do just about anything than sit with ourselves and ask ourselves a series of questions aimed at self-improvement. However, it's that continual assessment of ourselves that enables change. Sitting down and soul-searching helps you become clear. Chances are, if you've set aside the time to do the work, it means that you are open and are in the process of allowing the discomfort that accompanies growth.

Your moments matter. I'm never entirely sure I agree with the idea of not living some part of life in the future mindset. I think future thinking, in some forms, is very healthy as long as you stay out of anxiety and "what will happen" mode. If you are positive in your approach, future thinking can be fun and very productive. The futurist pattern to paying attention to your passion and keeping things in line with it, gives you moments with deeper meaning, presence and purpose. Don't underestimate your moments. In your moments you create an opportunity to think, behave, choose and relate accordingly.

Pick the questions below that inspire you and grab your journal. It's time to write down your vision for creating the Best Ever You and Creating Your Best Life.

Self-Evaluation: Your Vision for Your Best Life and Best Ever You

The Big Picture & Setting Goals:

1. What am I doing now?

2. What footprints am I leaving?

3. What matters most to me?

4. Am I positive?

5. Do I keep things in perspective and let the small things go?

6. Where am I going?

7. What do I want in the future?

8. What steps am I taking to get close to my dreams?

9. What has changed this past year?

10. What are my goals and have I written them down?

11. Has there been a change in your life making it necessary to change?

Attitude and Inspiration:

12. What is my outlook on life?

13. What are my core values?

14. What are my coping mechanisms? Do they work for me or against me?

15. What values and attitudes do I want to embody within myself and project to others in the world?

16. Am I practicing forgiveness?

17. Do I apologize?


18. Do I accept responsibility for myself?

19. Do I blame others?

20. Am I angry or impatient?

21. What is my mindset and how do I maintain it?

22. How do I keep my mindset intact despite outside differing influences?

23. How much do other people’s opinions matter and influence my mindset?

24. Do I believe anything is possible?

25. Have I failed a few times or more and how do I respond to failure?

26. Am I coachable and teachable?

27. Am I open to listen to others?

Motivation and Action:

28. Do I have exemplary character and integrity?

29. How am I spending my precious time and energy?

30. Am I practicing gratitude?

31. Have I got perspective on what really is important?

32. What do I need to change?

33. When I don't know how to do something do I seek assistance?

34. Am I feeling stuck?

35. Do I lead by example or is example leading me?

36. Am I polite, considerate and mannered?

37, Is my behavior online supporting my values, beliefs, goals, personality and in person being?

38. Do I practice random and unrecognized acts of kindness?

Substances and Environment:

39. Who surrounds me and am I surrounded by love?

40. Am I substance free?

41. Are those around me substance free?

42. Can I maintain my goals, beliefs and value system around others without being excluded?

43. What are my values, beliefs, and goals and does my behavior match them?

44. Am I avoiding or ignoring pain by using substances?

45. Am I trying to fit in or be accepted by joining the crowd and using substances?

46. Can I say no to a substance at a party, celebration, team event, family event or other event and be confident in myself, even if others create pressure of any kind.


47. Am I in good health?

48. Am I 20 or more pounds overweight and what am I doing about it?

49. What am I eating and drinking?

50. Have I had all relevant medical checkups and exams in the past year?

51. How do I manage my emotions?

52. How do I cope with chronic conditions?

53. Are self-love and self-worth abundant in my life?


54. What is my relationship with money?

55. What has changed in the my financial life in the past year?

56. Does my budget accurately reflect my means and my priorities?

57. Do I have the insurance I need?

58. Can I make a plan to pay off debt or at least move it to a lower-interest account?

59. If I've done well, what have I done to solidify my financial position?


60. How can I incorporate a healthy amount of exercise into my schedule?

61. Do I need to meet with a doctor to start an exercise plan or a trainer to tune up my workouts?

62. How do I manage stress?

63. Can I find a healthier way to handle stress?


64. How do I care for my appearance?

65. What do my looks say about me?

66. What do I want my appearance to say?

67. What do I like about my face and body?

68. Is the time and energy I spend on my appearance appropriate to my life at the moment?


69. What are my goals for where I want to live this year? Am I content with my home and neighborhood?

70. Do I want to find a better or more suitable home or make changes to my current one?

71. Do I feel "at home" where I live? If not, what would it take to get me to feel that way?


72. How is my relationship with myself?

73. Do I have a healthy balance of relationships in my life with my partner, friends, children, siblings, parents and others?

74. What is one change I would like to make in the way I relate to others?


75. What type of work would I like to do?

76. What has changed about my work life?

77. What am I doing to deal with those changes?

78. What am I doing to move closer to my career goals?


79. What do I do for fun?

80. Do I have enough fun or too much fun?

81. What relaxes me and renews me?

82. What excites me and enlivens me?

83. How can I find more leisure time in my schedule?

Religion and Spirituality:

84. What is my relationship with the Divine or with the human spirit?

85. What beliefs guide my life?

86. Am I closer or further from my spiritual center that I was a year ago?

87. Do I have people in my life who share my spiritual outlook or who can offer guidance in this area?

88. Do I experience a sense of community or lack of it?

Food and Nutrition:

89. What is my relationship with food?

90. Do I allow myself to eat something delicious but unhealthy once in a while?

91. Do I stay connected to my feelings of hunger and fullness?

92. Do I deny myself food when others are eating?

93. Does food run my life?


94. What do I do to help others?

95. What would I like to do to help others?

96. Do I readily volunteer to help or wait until someone asks?

The Long Run:

97. Have I made legal arrangements for what would happen to my kids or spouse if I became disabled or died?

98. Do I have life insurance?

99. What id my financial plan for retirement and old age?

100. Have a I created a living will, health-care proxy or power of attorney and discussed these plans with others?

You, your life and your moments matter. Each day, each hour and each moment you have the opportunity to stop and reassess how you are and how you feel. Start over if you need to. Examine the areas of your life that you wish were different and take meaningful and specific action to begin making each moment your best. Life is precious. Savor the moments.

About Elizabeth Hamilton-Guarino

Elizabeth Hamilton-Guarino is a 19-year veteran of the financial services and regulatory compliance training industry. Now, a recognized leader in personal development, Elizabeth is the founder and CEO of The Best Ever You Network, a brand with more than one million followers in social media and two million radio downloads on The Best Ever You Show.

With a mixture of humor and grace, Elizabeth helps people root in gratitude, discover motivation and implement positive, lasting change. An expert in mentoring people to market their strengths and achieve brand excellence, she works with clients worldwide to illuminate their light within, develop their best life and become their Best Ever You with gratitude-based behavior and belief systems.

Elizabeth’s book PERCOLATE – Let Your Best Self Filter Through (Hay House, 2014) has been called “charming” by Publisher’s Weekly, with “an ingenious extended coffee metaphor.” Guarino also ranks consistently as one of the top 40 social CEOs on Twitter and was just named a favorite by Oxford Said Business School. Her hashtags #BestEverYou and #TipstoBeYourBest are widely circulated.


bottom of page