31 questions and then some…

I love questions. In particular, I love making lists of questions. Perhaps that’s because life seems like a series of questions strung together over time [What are we doing? Where are my keys? What’s next? Why did I say that? Who cares? etc.] Making lists of questions feels really empowering to me. I guess that’s a positive way to re-frame my general confusion about the world. What do you think?

When I’m all muddled up and frustrated, I start pushing really hard for the solution to my problem. Thinking and churning and turning those wheels in my brain. However, almost without exception, I’ve found that find the ‘right’ solution is really about finding the ‘right’ question first. Easing up and focusing on the questions has been so helpful — not easy, never easy — but helpful.

Questions are my all-purpose tool to help expand my imagination, sharpen my focus, sort my thoughts and priorities, stimulate creativity, delve deeper into an issue, and occasionally arrive at an answer. Of course, questions are excellent for generating art too. For me, questions are the first step in getting things done. A better question = a better solution (or a better result or a deeper conversation or a more specific plan or more focused art or etc.) Has that been your experience?

What’s your relationship to questions? Do they help you?

To celebrate the month of August — or rather, to celebrate questions during the month of August —  I offer you a list of 31 random (hopefully, thought-provoking) questions, one for each day of this month. [I realize we are a little behind since August started last week, but you can double up for a few days. Hee.] The questions below are in no particular order and have no particular focus. Just good ol’ jumping-off-point questions for self-discovery and conversation. If you want to, use them as writing prompts, conversation starters, or opportunities for getting to know yourself during a meditative walk. Let me know how you do with them. I’m so curious! If there’s a question that you find particularly intriguing, then let me know that too. Perhaps that could be the focus for a future blog post.

For more content-specific questions, check out Story Corps’ Great Questions List.


  1. Where are you going?
  2. What is the next book you would like to read? Why?
  3. How do you feel about your name? Would you like to change it?
  4. When people see you walking down the street, what do they think?
  5. What is your favorite place? Why?
  6. What makes you feel invigorated?
  7. What was your last nightmare?
  8. What do you forbid yourself to do or to feel?
  9. What can you let go of?
  10. How do you greet people?
  11. How do you spend your evenings?
  12. Why did you make that choice?
  13. Who do you wish to be?
  14. Where do you want to live?
  15. How do you feel about food?
  16. How did you learn to think?
  17. What is your biggest pet peeve?
  18. Who makes you feel important?
  19. How would you spend a day by yourself?
  20. What is the elephant in the room?
  21. How are you different now than 5, 10, 15 years ago?
  22. What is the first thing you disclose to a stranger?
  23. Have you ever been in danger? How so?
  24. What is your fondest memory?
  25. How do you feel about wildlife?
  26. Who makes you smile?
  27. What makes you laugh?
  28. What situations make your stomach churn?
  29. When do you feel authentically yourself? What does that feel like?
  30. What are you planning to do 5 minutes from now?
  31. What is the best gift you’ll give this year?

Bonus Question #32: What will you do now that you know something you didn’t know before?

Bonus Reference to 32: If you were an undergraduate female in the 1990s obsessed with the song 32 Flavors by Ani DiFranco (um, me), then this list might have triggered a yearning for that song. If so, for sentimental purposes take a look at the YouTube video of Ani singing that song, And Lyrics to 32 Flavors by Ani DiFranco.

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