- What values or opinions do your enemies hold, that you would actually agree with if you were in their position?
- Are you taking enough risks in your life? What risks could you start taking?
- At what point in your life have you had the highest self-esteem?
- Consider and reflect on what might be your “favourite failure.”
- What is your biggest regret in life? Now what good came of it?
- How did you bond with one of the best friends you’ve ever had?
- How did your parents or caregivers try to influence or control your behaviour when you were growing up?
- How do the opinions of others affect you?
- How do you feel about asking for help?
- How much do your current goals reflect your desires vs someone else’s?
- If you could eliminate any one disease or illness from the world, what would you choose and why?
- Imagine that you have arrived at a closed door. What does it look like and what’s on the other side?
- In what ways are you currently self-sabotaging or holding yourself back?
- Take a task that you’ve been dreading and break it up into the smallest possible steps.
- Talk about a time that you are proud to have told someone “no.”
- The world would be a lot better if…
- Think about the last time you cried. Were they good or bad tears?
- What are some small things that other people have done that really make your day?
- What are some things that frustrate you? Can you find any values that explain why they bug you so much?
- What are some things that you could invest more money in to make life smoother and easier for yourself?
- What biases do you need to work on?
- What could you do to make your life more meaningful?
- What did you learn from your last relationship? If you haven’t had one, what could you learn from a relationship that you’ve observed?
- What do you need to give yourself more credit for?
- What do you wish you could do more quickly? What do you wish you could do more slowly?
- What does “ready” feel like to you? How did you know you were ready for a major step that you have taken in your life?
- What happens when you are angry?
- What is a boundary that you need to draw in your life?
- What is a made-up rule about your life that you are applying to yourself? How has this held you back and how might you change it?
- What is a positive habit that you would really like to cultivate? Why and how could you get started?
- What is a question that you are really scared to know the answer to?
- What is a reminder that you would like to tell yourself next time you are in a downward spiral?
- What is a view about the world that has changed for you as you’ve gotten older?
- …
P.s Since I published this post I’ve added additional questions to this list…
Download all x110 questions plus my AI skills for journal review
Subscribe for instant access to the full list of prompts & my AI prompts for journal analysis.
How do I use these journal prompts?
I’ve baked them into a Claude skill which grabs x3 questions from this list, and inserts them into my daily journal prompts every day, alongside some “evergreen” questions which occur everyday.
I find this keeps my journal fresh, instead of robotically answer the same questions everyday it actually triggers new responses, and more importantly, new actions from me everyday.
I have discovered I’ve been terribly guilty of endless journalling, and overthinking, but not actually doing anything about my worries. So I have a solution for that too…
Steal my Claude skills & AI prompts for journal analysis
I’m sure opinions will be divided on analogue vs digital journals;
On one hand, analogue journalling has a restive quality to it, and drives deeper reflection for me.
However there are HUGE benefits to a digital journal when it comes to retreospection and analysis…
Claude automatically inserts my daily journal responses into my digital journal in Obsidian. I then use Claude to scan my digital journal for my weekly and monthly reviews in my personal consistency system.
When connected to Claude, AI helps me surfaces recurring thought patterns & highlights contradictions in my thinking that I was completely unaware of myself. For example:
I might find myself stressing about how many garden chores I have to do, only for my daily flashback to surface a journal entry from last winter, where I’m yearning for some good, honest, outdoor labour!
My Claude skill for AI journal review does x4 things:
- A series of prompts
- Analysis and summary
- Suggestions and actions
- Flashback of same time period in previous years
I find these kind of serendipitous surfacing of old thoughts incredibly valuable, they reveal the gaps in my own self-awareness. I hope these have triggered some great responses for you. If you feel comfortable sharing, let me know in the comments, and feel free to suggest your own questions, which I’ll add here with credit!
You can grab the AI prompts that I created for my journal reviews here:
Download all x110 questions plus my AI skills for journal review
Subscribe for instant access to the full list of prompts & my AI prompts for journal analysis.
