30 questions to ask yourself every year

Every year, Spotify gives you your Wrapped. Your most-played songs, your favorite artists, all laid out for you.

But life doesn’t have this feature. (One of my many unfinished app ideas. Feel free to build it.)

Last year I came across Steph Ango’s (Obsidian CEO) 40 questions on his blog. I loved the concept. It’s like doing a comprehensive Wrapped for yourself.¹

So I tried to answer them, but hit a lot of resistance.

Many questions I couldn’t answer. Some I didn’t care about. Others I had no idea how to even approach.

That questionnaire never got finished. It’s still sitting in some folder. But reading what I did answer is still interesting.

This year I decided to start fresh, but this time I wrote my own questions.

The purpose is simple:

1. Summarize the year and adjust course
2. Leave a time capsule/save file so my future self can “return” to this year

If you have a habit of keeping records, this will be quick. If not, it might be painful. But that pain itself is a signal. Use this as an opportunity to start.

Feel free to use or modify this however you like.

# 30 questions to ask yourself every year

### 01 Input | What did you feed yourself this year
1. Favorite book or article
2. Favorite show or anime
3. Most-played songs
4. Best game you played
5. New creators or content sources you discovered
6. Places you visited

### 02 Output | What did you do this year
7. Did you hit your goals
8. Three most important things this year
9. New things you tried
10. Good habits you built
11. Things you quit or gave up
12. Best purchase (or what you spent the most on)

### 03 Experience | What did you feel this year
13. Most grateful for
14. Most sad about
15. Most excited about
16. Biggest regret
17. Any births, deaths, or major health events around you
18. New people or communities you met

### 04 Awareness | What did you learn this year
19. Most important quote or lesson
20. Old beliefs you changed
21. How are you different from last year (finances, health, happiness)
22. Weaknesses or blind spots you discovered
23. What turned out to be unimportant
24. What deserves more of your time

### 05 Looking ahead | What do you want next year
25. If you could only do 3 things, what would they be
26. What do you most want to remind yourself
27. Experiments you want to try
28. Things you want to do less or stop doing
29. Habits you want to do more
30. What kind of life do you want in 5 years