Retrospective Questions

TL;DR

Here’s a very long list of retrospective questions which, if used wisely and seldomly (at least twice per year; at most monthly), can help you spot patterns and behaviors you may want to address.

As a pro tip, get a notebook where you’ll be answering all these questions. Yeah, I know, probably a better idea nowadays would be to store it digitally and then feed it into ChatGPT for some conclusions, but there’s still something with actually writing stuff down by hand (you can still OCR it if your writing is readable 🙂).

Anyways, hope this proves to be useful on your improvement path 💪

Disclaimer: I’m not the author of these questions. But, for the life of me, I can’t remember where I got these from (yes, I Googled and ChatGPT-ed). If you do, please ping me an I’ll update the post.

The Questions™

1. Who am I?
2. Am I living the life I want? Why yes or why no?
3. If I had 1 year to live, what would I do?
4. If I had 1 month to live, what would I do?
5. If I had 1 week to live, what would I do?
6. If I had 1 day to live, what would I do?
7. If I had 1 hour to live, what would I do?
8. If I had 1 minute to live, what would I do?
9. What would I regret the most if I died right now?
10. What advice would I give to myself 3 years ago?
11. What advice would I give to myself 1 year ago?
12. What advice would I give to myself 1 month ago?
13. What advice would I give to myself 1 week ago?
14. What had to be done yesterday, and I didn’t do it?
15. What do I want to achieve until the end of my life?
16. What do I want to achieve in 5 years?
17. What do I want to achieve in 3 years?
18. What do I want to achieve in 1 year?
19. What do I want to stay remembered for?
20. Why are these things important to me?
21. What is stopping me and how can I achieve them?
22. Do I know people that achieved similar goals?
23. What opportunities am I seeing in my environment, and how can I use them?
24. Have my recent activities brought me closer to my goals?
25. What do I need to do in the next week to get closer to completing my goals?
26. What’s my biggest priority for next week?
27. What will I do about it?
28. What can I do so that the following week will be less stressful?
29. What was I avoiding to do, and it had to be done?
30. What prevented me from doing that?
31. What were my wins in the last week?
32. What did I learn in the last week?
33. What moment was unforgettable in the last week and why?
34. What am I grateful for?
35. Do I love my self, and why?
36. What is the one thing I could do for free till the rest of my life?
37. Do I like what I do, or am I at least trying to make it work?
38. What’s my biggest fear? How can I overcome it?
39. Who are the 5 people that I spend the most time with?
40. Do these people motivate or limit me?
41. Who inspires/motivates me the most currently? Why?
42. Who’s the most important person in my life, and have I dedicated her/him enough of my time?
43. Who am I going to dedicate the time in the next week?
44. Who deserves my gratitude this week?
45. How, whom and why can I help?
46. Have I dedicated enough time to myself?
47. Which habits should I keep on enforcing?
48. Which habits should I get rid of?
49. What was the time sink last week?
50. Is this what I do today be important in 1 year?
51. Is this what I do today be important in 3 years?
52. Is this what I do today be important in 5 years?
53. What can I simplify in my life?
54. What can I delegate in the next week and to whom?
55. If life is so short, why do we do so many things we don’t like and like so many things we’re not doing?
56. When all’s said and done, will you have the feeling that you said more than did?
57. If the average human life span would be 40 years – how would you live your life?
58. How much of your life’s path are you controlling?
59. If you could offer one advice to the newborn (presuming it could understand you I guess), what would it be?
60. Who would you like to have as a mentor in your life? How can you get to this person?
61. Is there something you didn’t do, and you really want to do it? What’s stopping you?
62. What would I do if I had no limits in terms of money, time and resources?
63. If you had to move to a different country, what would it be?
64. Would you rather be a worried genius or a happy fool?
65. Are you the sort of friend you’d like to have?
66. Has your greatest fear ever come true?
67. Do you remember a time 5 years ago when you were really stressed about something – is this important today?
68. If you win a lottery would you quit your job and why?
69. Do you feel like you’ve lived today’s day 100 times?
70. If I had a million $, what would I do and why?
71. If everyone you know would die tomorrow, who would you visit today?
72. Would you be willing to lower your life expectancy for 10 years in an exchange for being extremely pretty and famous?
73. Where did you live primarily in the past week? In the past, present or future?
74. If I had more guts, willing to take any risk, what would I do?
75. Decisions are made here and now. Are you making your decisions or are they being made for you?
76. What’s the purpose of my life?
77. What will I do right now so that I would live a life with purpose?
78. Is the current work I do meaningful for me?
79. Is this job going to give me a chance to develop?
80. Am I going to learn new things?
81. Will I have the opportunity for recognition and achievement?
82. Am I going to be given responsibility?

Dude, this is too much

If these feel too much, it’s because they should. Improvement doesn’t come from thinking about your life for 2 minutes. Nor 20 (although a great step up from 2, or worse yet: 0). It usually takes me about an hour and a half to go through these and write them down. YMMV.

However, since you won’t be going through the whole list weekly, here are a few to ask yourself on a weekly basis (ideally when you prep your next weeks’ agenda):

1. What’s my biggest priority for next week?
2. What will I do about it?
3. What can I do so that the following week will be less stressful?

Protip: work on that biggest thing (as Brian Tracy says: eat that frog!) first thing in the morning!

Conclusion

Really, there’s not much to say here other than to challenge you to do it and see if it moves the needle for you in your life. Good luck!