100 Questions: How well do you know you?


Self-Awareness is the cornerstone of maturity. Without it, a person will not see herself clearly, will lean toward characterizing herself as a perpetual victim or as self-appointment champion (unproven without temperance or merit), and fail to harness her true impact on others and the world around her. In short, if you manage to skip intentional self-awareness work, you’ve cheated yourself and the rest of us are likely suffering because of it. 


By the same token, tribalism is real. Tribalism is how we consciously and subconsciously surround ourselves with people who are a lot like us. Tribalism makes us feel safe, and it can also insulate us from reality. If you are walking a dangerous path and your tribe is doing the same, who is there to sound the alarm, to raise difficult questions?


The questions below have two purposes. First, I dare you to answer them for yourself. Yes, it’ll take you a while. Thankfully, self-awareness is the kind of thing that you do in chunks. Pondering a topic is sometimes the kind of thing you pick up, set down, and come back to. The second purpose is a list of questions to pose to your sister-friends. Find out what you’re working with and whether you all are closely aligned. By studying them, you might be amazed at what you learn about yourself.



  1. What is greatness?
  2. What would make you great?  
  3. What do you desire your legacy to be?
  4. What’s your greatest insecurity about your hope of greatness?
  5. Who, in your life, personifies greatness?  Why?  How?
  6. What is beautiful?
  7. What is ugly?
  8. Where do you encounter beauty on a regular basis? 
  9. Where in your life/world have you created beauty?
  10. What have you defiled or desecrated? 
  11. What is the most beautiful quote, scripture, or passage that you’ve ever read?



  1. What does death represent to you? 
  2. Describe what you would like your funeral to be like. 
  3. Describe what you think it would be like to be an unrecognized attendee at your own funeral. What do you think people’s spoken memories of you would include?
  4. How would you plan the funeral of someone you loved (a parent, a spouse, lover, child, dear friend, etc)?  How would you honor their life?
  5. Whose death has been deeply impactful for you? Why?
  6. What experiences or achievements must you have, lest you pass away feeling as if you weren’t finished living? (Put differently, What things must you accomplish in order to feel like your life is full?  Complete?)



  1. What would you like to be asked?
  2. What do you hate to be asked?
  3. What question(s) do you ALWAYS have a difficult time answering?
  4. What makes you feel embarrassed?
  5. What are the contradictions in your life?
  6. Where are those places where there are gaps between what you think and what you feel?
  7. If someone, not necessarily romantically, wanted to get to know you really well, what should they know?
  8. What do you need to feel/be confident? 
  9. What makes you feel threatened or insecure?
  10. What do you love about your body? What would you change?  Why?
  11. How do you honor your body? 
  12. How do you manage your feelings? 
  13. What are your hobbies? What hobbies would you like to cultivate?


Dating and Sex:

  1. How do you flirt?
  2. What is your sexual orientation? How do you know?
  3. Describe the kind of people whose company you enjoy romantically?
  4. What is pleasure?
  5. What attracts you FIRST to someone?
  6. What do you love about the body of your lover? That person’s mind?
  7. Do you feel confident and comfortable during sex? What strengthens or diminishes your confidence and comfort during sex?
  8. What makes sex great?
  9. What is romance?
  10. What is love?
  11. What was your first sexual encounter like?
  12. Describe your first orgasm.
  13. Describe your first sexual disappointment.
  14. Describe your first adult dating/romantic relationship.
  15. Have you ever been celibate for an extended period of time (1 year or more)? Why? Would you do it again?
  16. What is your opinion on casual sex?
  17. What is sexy? What/who helped you to define sexy?
  18. Are you sexy?
  19. What is sensual? Is there a difference between sexual and sensual?
  20. What do you wish your partner knew about you? Have you told them?
  21. Is there a past partner or lover who you think of as “the one who got away”?



  1. Do you believe in a higher power, i.e., God?
  2. What does God mean to you?
  3. What’s your opinion of organized religion?
  4. How does your belief or disbelief about God and or religion inform your life?
  5. How do you explain the inception of humanity and the world? Creationism, Evolution, Big Bang, something else?  Why?
  6. What is something about life that you just believe although you cannot point to a sacred text or other “substantiating belief system”?
  7. What is the most beautiful quote, scripture, passage that you’ve ever read?
  8. What makes your spiritual beliefs and practices meaningful to you?
  9. Did you consciously choose your spiritual practice?


Relationships and Community

  1. What makes you feel loved?
  2. How do you show love?
  3. What scares you?
  4. What do you crave?
  5. Who are you?
  6. What makes you feel understood and embraced?  Misunderstood?
  7. How (well) do you fit in with your blood family?
  8. What do you owe family?
  9. What do you think is the first thing others notice about you?
  10. What, if anything, is your obligation to your fellow man?
  11. Have you ever felt immediately connected to someone, like an instant friendship burst into your heart? What explains that connection?



  1. Have you ever disliked someone nearly immediately upon meeting them? Why and what did that feel like?
  2. What causes you to ignore and disregard someone?
  3. Who has campaigned to be part of your life that you have locked out? Why are they campaigning and why have you locked them out?
  4. What is hatred?
  5. Who/What have you hated?  Why? 
  6. How does your hatred of ______ (fill in the blank) impact you?
  7. What is unforgivable?
  8. Do you hold grudges? Why or why not?
  9. Who has been the hardest person in your life to love? To forgive? Why?
  10. How do you forgive? How do you know you’ve forgiven, that you’re over it?  How does someone know that you’ve forgiven them?
  11. What’s the difference between not forgiving and a “forgive and move on to cut my losses” attitude?
  12. Who have you taken a risk on restoring to love? What did you learn from that experience? 

The World Around You

  1. How do you contribute to the world?
  2. What items in your physical space most represent how you see yourself?
  3. If you were being forced to purge your living space of things you don’t use, what would you have to get rid of?  Would you find it difficult to get rid of them?
  4. What do you need to clean up?
  5. What items do you own that you would NOT re-purchase?
  6. If you had a fire and could only go back into your home once without losing your life, what would you save?
  7. Where is your favorite place to go in your neighborhood? Community? Region?
  8. What, if anything, do you like about “the great outdoors”?
  9. In terms of your neighborhood/community, what does your world look like? Do you find it strengthening, a source of peace, a reminder of things you don’t like, stressful…?
  10. Do you believe that climate change is real? Do you believe you can have an impact on it, positive or negative? 
  11. What is your favorite thing about each season of the year? What’s your favorite season?
  12. Nature is_____________________________________________________________.
  13. What parts of the world (think countries, forests, mountains, etc.) are you curious about and want to experience?



  1. What makes you feel smart? Not so smart?
  2. What areas of your sense of worldliness do you want to deepen?
  3. If you had access to only one, formal education or life’s lessons, how do you think your station in life would be impacted?
  4. What is the purpose of education? 



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