Okay, it’s not just one question, it’s a bunch of questions, as in 64!

(For the quick, “Get to the questions already!” Click here: 2019 Year in Review.)

Those of you that know me, know about these annual questions. Around twenty years ago, they were passed along to me and I dove head in. I’ve worked with these questions at the end of every year and the beginning of the new year, ever since.

I love looking back on the past twelve months, for better or for worse. I like to scroll back and ponder what I did, how I spent precious time, what made me ridiculously happy and where I screwed up royally. I also love dipping into the future and imagining what’s to come! As I maneuver my way through these questions, I predictably find myself shaking my head a little bit and murmuring under my breath, “Oh my goodness, I forgot about that!” 

Nonetheless, I find this process really enlightening and rich. 
I think you will too.

It’s something for you to have fun with, to share with others (cut them up into strips and toss them in a bowl at a holiday party!) or just for you: gather the questions around you, grab a huge mug of hot coffee and drop in. (That’s what I do.) 

Here’s the full list:


1. What was the smartest decision you made in 2019?

2. What decision have you made for 2020 that you are really intent on and proud about?

3. What is one dumb thing you did in 2019 for which you are willing to forgive yourself?

4. What one word best sums up your 2019 experience?

5. What was your single biggest success of 2019?

6. What do you imagine, or expect, will be your biggest success of 2020?

7. Name three disappointments you had in 2019?

8. List ten of your greatest 2019 pleasures. Circle the ones you’d like to repeat in 2020.

9. What was the most outrageous adventure you had in 2019?

10. What was the wisest advice you received in 2019?

11. What advice do you give to yourself for 2020?

12. Name three people who had the most impact on you and your life in 2019?

13. If you could go back and do one thing differently in 2019 what would it be?

14. What was the biggest talent you demonstrated in 2019?

15. What is one, as of yet, undeveloped talent you possess and are most willing to explore in 2020?

16. Who was the one person, other than yourself, you most loved at the beginning of 2019?
How do you feel about this person right now?

17. Who is the one person you love most at the beginning of 2020? Explain briefly why.

18. Name the single event you are most looking forward to in January 2020?

19. Give one reason you are better at commitment in relationship than you were a year ago?

20. Name the three areas of your life you feel moved forward in 2019?

21. Name the one activity you are most willing to delegate more time to in 2020?

22. What was something that turned out better than you expected in 2019?

23. Name one major indulgence you gave yourself in 2019?

24. What new major indulgence are you willing to experience in 2020?

25. Name one object you bought in 2019 that gave you the most pleasure and satisfaction?

26. Name the one person that gave you the most pleasure and satisfaction in 2019?

27. What do you expect will be your greatest source of pleasure and satisfaction in 2020?

28. What was the best idea you had in 2019?

29. What are you most happy about having completed in 2019?

30. What would you most like to complete in 2020?

31. What is the one thing you are most committed to for 2020?

32. What was the biggest financial surprise of 2019?

33. What are you now planning that you think will most affect your personal wealth in 2020?

34. What one friend didn’t you connect with in 2019 that you’d most like to see in 2020?

35. Who were three people in your life you most enjoyed getting to know in 2019?

36. What was one compliment you received in 2019 that really pleasured you?

37. What one compliment would you pay yourself about your 2019 performance?

38. What one compliment would you most like to receive and from whom in 2020?

39. What is one way you could be more open/honest/vulnerable in 2020?

40. Who is the one person you met in 2019 you would most like to get to know better?

41. What is the single biggest risk you took for yourself in 2019?

42. What is the biggest risk you are now willing to take in 2020?

43. What about 2019 totally surprised you in comparison to what you expected?

44. What was the funniest thing that happened to you in 2019?

45. What was the saddest thing that happened in your life in 2019?

46. What new thing did you do in 2019 that you would most like to repeat in 2020?

47. What new thing do you think you will do in 2020 that you have never done before?

48. What one single thing are you most willing to eliminate from your life in 2020?

49. If you could choose one day in 2019 to completely duplicate in 2020, which day would it be?

50. What is the biggest change in you that someone who hasn’t seen you in the past year would notice?

51. What do you expect will be the biggest change you will undergo in 2020?

52. Name your three greatest entertainment pleasures in 2019? – movies, tv, live performances, etc

53. What was your most memorable and pleasurable meal in 2019?

54. What was the most loving experience you had in 2019?

55. What workshop, tape, or book most impacted your personal growth in 2019?

56. What new workshops, courses or books are you planning to use for yourself in 2020?

57. Name something new and extravagant you are willing to do for yourself early in 2020?

58. What is one brand new way to earn money you are willing to consider in 2020?

59. What was most exciting about your work in 2019?

60. What about your work are you most looking forward to in 2020?

61. What about your work are you most committed to changing in 2020?

62. What is the one place you most enjoyed spending time in 2019?

63. What new place would you most like to visit in 2020?

64. What one word would you most like to have as your theme in 2020?

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