57 Questions for Reflection

The period of time from Rosh Hashana to Yom Kippur, known as the Aseret Yemei Teshuva is a time for reflection.   When we are honest with ourselves, we learn things about ourselves we never knew, find answers to questions we had been too afraid to ask and discover unexpected solutions to problems we feared to acknowledge.  Please use these questions from Areyvut as a way to reflect and engage family and friends in meaningful conversation.  

1. Who are you?

2. Do you like who you are?

3. Are you at peace with the person you see in the mirror?

4. Do you practice ‘self love’ or ‘self loathing’?

5. What does praise and admiration sound like to you?

6. What do you owe yourself?

7. Would others agree with your description of yourself?

8. Do you want to know how other’s see you or is ignorance bliss?

9. Who is someone you trust who could provide valuable perspective on how others see you?

10. From whom do you need to ask forgiveness?

11. Whom do you need to forgive?

12. For what mistakes do you need to forgive yourself?

13. Have you ever felt embedded in a community? What were those experiences like?

14. Have you ever felt left out of a community?

15. What does it take to become a member of a community?

16. Do you have to personally like, or feel connected to, everyone in your community?

17. How do you know who is in your community?

18. Have you ever clearly known what the world, or part of the world, needed from you?

19. What do you want to give the world?

20. Do you believe in the possibility of change?

21. What are the 3 things in your life that you would like to change?

22. What was your biggest worry five years ago? Did it come true? Do you still feel the same about it at this minute?

23. What are your biggest worries and fears today?

24. If your biggest fears came true, would it matter in five years from now?

25. How often do you let your fears hold you back?

26. What is your biggest dream in life?  Is it something possible to achieve?

27. What is the first step in making the dream come true?  

28. What stops you from making the first step towards your dream?

29. Whose permission are you wanting for to achieve your goals? Will it actually come?

30. If you woke up tomorrow with no fear, what would you do first?

31. Forget your real age for a second – How old are you at heart?  Do you like that age or do want to change it?

32. Can you picture the child you once were, what were they really good at?

33. What advice would you give the 5 year old you? The 10 year old you?  The 20 year old you?

34. What have you seen or experienced that you would want your children to know about?

35. What would you like to be remembered for?

36. What are the miracles that you see in your life?

37. What is a promise that you made that you still need to fulfill?

38. What concrete steps can you take to fulfill that promise?

39. What advice do wish you had received five years ago?

40. What blessing would you like to receive in the coming year?

41. What songs would you put on the sound track of your life?  

42. If your life were a movie, would you enjoy watching it?

43. What would you regret not doing in your life?

44. If you could live one day over and over again, what would you choose to do?

45. What does success mean to you?

46. What do you look forward to most in life?

47. What bad habits do you want to ditch?

48. What inspires you?

49. Whom do you look up to and why?

50. Do the people you love most know how much you love them?

51. Based on your current day-to-day life, what do you expect to achieve in 5 years from now?

52. Are you holding onto something that you need to put behind you?

53. Is there any you consider to be unforgivable?

54. Who do you need to get in touch with because it’s been to long?

55. What do you need to learn but won’t admit to?

56. What are you thankful for, this moment?

57. What questions here have you skipped over because they are too hard for you to handle?