100 Journal Prompts from 5 Years of Weekly Reflection

I have written a reflection every week for more than five years. Not daily, not perfectly, but every week, on the same set of questions, refined each time one of them stopped earning its place. The prompts below are what survived that filter.

Most journaling prompt lists are written by someone who has not kept the habit. You can tell, because the questions are pleasant and produce nothing. A prompt earns its spot when it makes you write something you did not want to write. That is the only test I applied here.

They are grouped by when you would use them, because that is how the practice works week to week: a different question on a rushed Tuesday morning than at a genuine crossroads. Start anywhere. If you are trying to build a daily habit, read why daily journaling failed for me and the 90-second set that survived first. If you want the weekly review that produced this list, jump to group three.

100 journal prompts

Prompts 1 to 10: morning

Before the day gets its hands on you.

1. What is the one thing today that, if it goes well, makes everything else negotiable?
2. Which task am I avoiding, and what is the fear underneath it?
3. What could go wrong today, and how do I want to react when it does?
4. Who will I speak to today, and what do I want them to leave with?
5. What am I doing today only because somebody expects it?
6. If today were an ordinary Tuesday in the life I say I want, what would be in it?
7. What can I do before 9am that I will be glad about at 9pm?
8. Which of today's problems are inside my control, and which am I renting space for?
9. What did I sleep badly about, and is it a problem or a mood?
10. What would make today good enough, and can I stop optimising past that?

Prompt 3 is the oldest one in my rotation. The Stoics called it premeditatio malorum, picturing the bad outcome on purpose so it has less power when it arrives. It is also the least pleasant question here, which is usually a sign a prompt is working.

Prompts 11 to 20: five minutes, on a busy day

Short journaling prompts for the days when the honest choice is five minutes or nothing.

11. Summarise the day in one sentence, no editing.
12. What is on my mind right now, before I start explaining it to myself?
13. One thing that went better than expected.
14. One thing I would do differently, in ten words.
15. Where did my attention go today that I did not choose?
16. Who helped me today, and did I tell them?
17. What am I pretending not to notice?
18. What is the smallest next step on the thing I keep postponing?
19. What am I grateful for that I also had last week and stopped seeing?
20. If I remember one moment from today in a year, which should it be?

Prompts 21 to 30: the weekly review

This is the group that became my weekly reflection template. Somewhere between five and thirty minutes, depending on the week.

21. Where am I writing this from, and what did the week look like from the outside?
22. What happened this week that I will still care about in a year?
23. What disturbed my inner peace this week?
24. What did I do that does not match the person I say I am?
25. Which habit would have prevented the worst moment of my week?
26. What did I finish, not just start?
27. Where did I spend time that bought me nothing?
28. Which relationship got my attention this week, and which got the leftovers?
29. What did I learn the hard way?
30. Reading this entry in five years, what will I wish I had written down?

Prompt 30 is the one that changes how you write. Once you have an archive going back years, and you have gone back and read your own worst weeks, you write differently: less performing, more recording.

I do believe life operates in cycles, kind of like a rollercoaster. Sometimes it goes up, sometimes it goes down.

From one of my own weekly reflections, quoted in full in five years of weekly stoic reflection

Prompts 31 to 40: anger, envy, and what upset you

The section of my template I resisted longest and now consider the most useful. Triggers are information about what you expect from the world.

31. What made me angry this week, and what does that say about what I expected?
32. Whom did I envy, and what specifically do they have that I want?
33. Which comment stayed with me longer than it deserved, and why that one?
34. Where did I confuse being disrespected with being disagreed with?
35. What would I have needed to believe for that situation not to upset me?
36. When did I last feel defensive, and what was I protecting?
37. Which trigger keeps coming back wearing different clothes?
38. Who would not have been bothered by what bothered me, and what do they understand that I do not?
39. What did I want somebody to say that I never asked for?
40. Where am I still keeping score?

Prompts 41 to 50: failure, and where you can improve

41. What failed this week, and was it execution or judgement?
42. What did I get wrong that I predicted correctly a month ago?
43. Where was I hard on myself in a way that helped nobody?
44. What am I calling a setback that is closer to information?
45. Which mistake have I now made twice, and what changes before the third?
46. What did I avoid learning because it would mean admitting something?
47. Where did I choose comfort and call it patience?
48. What would the version of me from five years ago be impressed by, and what would disappoint them?
49. What am I good at that I have quietly stopped practising?
50. Which failure am I still explaining instead of using?

Weekly Reflection Template (Word)DOCX ↓ Weekly Reflection Template (PDF)PDF ↓

Prompts 51 to 60: gratitude, without the platitudes

51. Three things, and let one of them be small enough to be embarrassing.
52. What do I have right now that I once wanted badly?
53. Who reached out to me first, and how long has it been since I did?
54. What did my body do for me today without being asked?
55. What would I miss most if it vanished tomorrow, and have I noticed it this month?
56. Which ordinary thing today would have amazed me at sixteen?
57. What went wrong that could have gone much worse?
58. Who taught me something I now use without crediting them?
59. What is good about this exact phase of life that I will only recognise later?
60. What am I grateful for that money did not buy?

Prompts 61 to 70: goals and progress

61. What did I move forward this week, professionally and privately?
62. Is this goal mine, or did I inherit it from a room I wanted to impress?
63. What am I optimising for, in one word, and is that honest?
64. What would I stop doing if I trusted the main thing to work?
65. What does done look like, specifically, and how will I know?
66. Which number am I watching because it is easy rather than because it matters?
67. What is the goal behind this goal?
68. If the outcome is not in my control, what is the effort I can fully own?
69. Which small step, repeated weekly for a year, would change the most?
70. What am I building that I would keep building with no audience?

Prompt 68 is the trichotomy of control, the Stoic habit of separating what you fully control, partly control, and do not control at all. Applied to goals it means setting the target on your preparation rather than the result.

Prompts 71 to 80: self-discovery

These are the journal prompts for self-discovery I used when I was working out what I wanted to do next, and they work better on paper than in your head.

71. What do I do when nobody is watching and nobody is paying?
72. What could I talk about for thirty minutes with no preparation?
73. What did I do at ten years old, before rewards existed?
74. Which work makes me forget to eat?
75. Which people leave me with more energy than I arrived with?
76. What comes easily to me that others find hard, and have I dismissed it for exactly that reason?
77. What would I still do if I never had to work for money again?
78. Which compliment do I receive repeatedly and keep waving away?
79. Where do I have an unfair advantage: knowledge, network, timing, or taste?
80. What makes me angry about how things are done, and could I be the one to fix it?

Prompts 81 to 90: the big crossroads

Deep journal prompts for the once-in-a-decade decisions. This group is the one I ran before quitting a six-figure job at 27.

81. Which path feels heavy, and which feels light?
82. What would I choose if I could tell nobody about it?
83. If both options failed in five years, which failure would I be proud of?
84. Can I live with the worst realistic case? If not, what would make it survivable?
85. Will I regret not having tried this when I am old and explaining my life to somebody?
86. What am I afraid people will think, and whose opinion is that specifically?
87. What have I outgrown but not yet put down?
88. Which story about myself is no longer true?
89. What am I waiting for permission to do?
90. If I had to decide today with no further information, what would I choose?

Prompts 91 to 100: when life is hard

The questions worth having ready before you need them.

91. What is this phase trying to teach me?
92. What is in my control right now, even if it is only the next hour?
93. What have I already survived that was worse than this?
94. Who can I tell the truth to this week?
95. What am I numbing, and what would I feel if I stopped?
96. What would I say to a friend in exactly this situation?
97. What is the smallest thing that reliably makes tomorrow easier?
98. What will I be glad I did not do during this period?
99. What is this costing me, and what is it buying?
100. If this is the down phase of the cycle, what do I want to have built by the time it turns?

We will also find that we are spending less time than we used to wishing things could be different, and more time enjoying things as they are.

William B. Irvine, A Guide to the Good Life

Turning prompts into a practice

A list of journal questions is easy to enjoy and easy to abandon. Three things made mine survive five years:

• A fixed cadence beats a good mood. I picked weekly, because daily made me write filler and monthly made me forget the details. Sunday evening, most weeks. The full argument for weekly is a separate piece.
• The same questions every time. Rotating prompts feels productive and destroys the thing that makes this valuable, which is comparing this week against last year on the same axis.
• Write it where you will find it again. The archive is the product. Rereading my own entry from the worst month of a given year has changed more decisions than any single new insight.

If you want the version I use myself, with the sections in order and space to write, the template above is the same file I open every week. It is free, and there is nothing to sign up for.