100 Questions

by Michael Simmons on Mar 14, 2009

When I was in high school, I read the book “How to Think Like Leonardo Da Vinci” by Michael Gelb, which I highly recommend. One of the exercises in the book was listing the first 100 questions that come to your mind via your stream of consciousness. The presumption was that the questions would reveal themes in your life that are important to you, which you might want to look into further. Here’s mine now:

FYI – If you want to do this, block at least 20-30 minutes aside.

1. How does one live life to his her fullest potential?
2. How can I be focused on what’s important to me and leverage new technologies like facebook, twitter, and email without getting distracted?
3. How can I surround myself with more people who are committed to living question #1?
4. How can I build a self-development program for myself that answers question #1?
5. How can I experience the time with Halle and not feel that I’m getting behind on work?
6. How can I most fully express myself without losing important current or potential clients?
7. What are the most important questions I should be asking myself on a daily basis?
8. How can I build the closest relationships possible with my family?
9. What are my blind spots?
10. What’s right in front of me that I want to see, but can’t see for some reason?
11. What books should I read that best answer question #1?
12. What movies should I watch that best answer question #1?
13. What mentors should I have that best answer question #1?
14. What mentors are in my life right now that I don’t see?
15. How can my life be a living prayer?
16. How do I overcome life’s ‘little’ temptations, which lead to distraction?
17. How can I have the biggest impact on the world?
18. What are my biggest strengths?
19. How can I most effectively let go of fear, jealousy, and anger?
20. What is the best way to meditate?
21. Should I use an air purifier at home?
22. How can I have the most healthy diet and that is the cheapest and takes the least amount of time to prepare?
23. How can I setup my work environment to have better posture?
24. What would the ideal exercise program for my lifestyle and health goals look like?
25. If I were to pursue question #1 1,000%, what would my life look like?
26. What would an idealized version of myself look like?
27. How can I be that person everyday?
28. How can I be the best father?
29. How can I be the best son?
30. How can I be the best husband?
31. How can I be the best friend?
32. How should I prioritize my life?
33. Should I get two computer monitors?
34. How can I be more fashionable? :)
35. What are my deepest fears?
36. How can I maximize my courage?
37. How should I draw the line between what I know at more core and fulfilling different roles I play as a citizen, entrepreneur, etc.?
38. How much of a rebel do I want to be?
39. How can I most effectively share myself with others?
40. What should I hold back when sharing myself with others?
41. How do I know when I’m unintentionally turning people off or unexpectedly resonating with them?
42. How does one gain basic competency as an engineer or scientist without any academic training in these? Is it worth it?
43. How will technology change the identity of what it means to be human in the 21st century?
44. How I can maximize positive and minimize negative black swans in my life?
45. How can I ensure Halle’s safety while maximizing her freedom?
46. How can I help Halle find her passions and become world-class at the one(s) that are most important to her?
47. At a core level, what is money?
48. Is watching TV series that I like a good relaxation technique that is sometimes inspiring or is it a distraction?
49. How can I help our cat get over his sickness?
50. What is the best age for a child to get a dog?
51. Should I respond to all of my emails?
52. How can I make meditation a lifestyle?
53. How can I remember what’s important to me as I go through the busyness of life?
54. How can I feel the emotion of grattitude, forgiveness, easygoingness, and unconditional love on a moment-to-moment basis?
55. How I can more easily role with the punches of life instead of trying to fight them?
56. How can I judge myself and others less?
57. Am I over-thinking things or am I afraid that others will think I’m over-thinking things, or both? Does it matter?
58. What should I be saying ‘no’ to?
59. What people in my life should I be spending more time around?
60. What people in my life should I be spending less time around?
61. How much should I cater my lifestyle to what my mom wants?
62. How can I practice sleeping on my back?
63. How can I find a local masseuse / chiropractor / etc. who is effective that I am aligned with and who I can visit regularly?
64. How can I find someone who I would trust to watch Halle?
65. How can Sheena and I most effectively live question #1 with and for each other?
66. Is the most effective way to have a positive impact on the world to be the best person you can be or is it to build a scalable organization with a culture/product that helps billions of people? Are these the same question?
67. What questions will I be asking about life 10 years from now?
68. How can we scale Extreme Entrepreneurship to impact billions of people?
69. What salary do I need to live my ideal life?
70. What role does luck play in my life?
71. What is luck?
72. Am I overly cynical of energy work?
73. What am I too skeptical about?
74. What am I not skeptical enough about?
75. How can I be a better driver?
76. What is the ideal number of hours of work per week to do?
77. What toll is the number of hours I work taking on my body, if any?
78. How can I spend three hours per day for ten years focused on question #1?
79. How can I recontextualize what it means to do nothing?
80. How can I be fully present when I’m with Halle?
81. What Halle trying to communicate to me when she makes sounds?
82. How can I be a tough love person with Halle as she gets older?
83. When should I give feedback to someone else? When should I keep the feedback to myself?
84. How can I feel awake and fully energized every day?
85. How can I make our home more energy efficient?
86. What should I be doing with my time with Halle?
87. Are multi-vitamins bad for you?
88. How can I bring stillness into my life?
89. How can I be more true to myself?
90. How can I recontextualize my life around be productive and not just feeling productive?
91. How can I be a better speaker?
92. How can I be a better salesperson?
93. How can I recruit people to the team who aligned and who deliver?
94. How can we have awesome events when Sheena and I aren’t there?
95. How can we create a bug-free, usable, fast-loading web site?
96. How can I learn Chinese? Should I learn Chinese?
97. How can we webcast our events to a larger audience?
98. How can we most effectively market our events?
99. How can we more effectively partner with our clients?
100. What is the best way to teach entrepreneurship?



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I'm the co-founder of Empact, one of the leading entrepreneurship education organizations in the world. I'm obsessed with understanding how we all can lead meaningful lives that have a positive social impact. I love probing into the truth of how we experience life. I believe that challenges are what make us grow the most, and I openly share my experiences. Continue reading…


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