Deep Dive Problem-solving Journaling Prompts

Pick one problem you're facing. Write it down. Then create a priority matrix: Draw 4 boxes labeled 'Urgent & Important', 'Important but Not Urgent', 'Urgent but Not Important', 'Neither'. Place this problem in a box. Then write about why it belongs there and how to prioritize it.

Think of one challenge you want to solve. Write it down. Then explore: What resources do I need? What do I already have? What's missing? Who could help? What information do I need? Then write about what resources you need and how to get them.

Think of one situation you're trying to figure out. Write it down. Then explore: What do I know? What don't I know? What information would help? Where could I get it? Who might have insights? Then write about what information would help you understand it better.

Think of one obstacle you're working through. Write it down. Then think of a similar obstacle you've faced before. Write about: What strategies worked then? What didn't work? How is this obstacle similar or different? Then write about what strategies might work now.

Think of one decision you need to make. Write it down. Create 2-3 columns for your options. Under each option, write pros and cons. Then, turn the page (or wait 5 minutes) and without looking back, write the pros and cons you remember. Compare: What did you forget? What does that say about what matters? Then write about what criteria matter most.

Think of one issue you're addressing. Write it down. Then think of another issue. Write about: How are they connected? Do they have a common root? How does addressing one affect the other? Then write about how your issues connect to each other.

Think of one conflict you're navigating. Write it down. Then explore it from 3 perspectives: Your perspective, the other person's perspective (as you understand it), and an outside observer's perspective. Then write about what perspectives help you understand it better.

Think of one question you're trying to answer. Write it down. Then explore: What do I already know? What don't I know? What questions would help me find the answer? How can I explore this? Then write about how curiosity helps you find answers.

Think of one difficulty you're facing. Write it down. Then explore: What support would help? Who could provide it? What do I need to ask for? How can I receive support? Then write about what support would help you through this.

Think of one barrier you want to overcome. Write it down. Then explore: What strengths do I have? How have I overcome barriers before? What strengths can I use here? How can I leverage them? Then write about what strengths you can use.

Think of one puzzle you're trying to solve. Write it down. Then break it into smaller pieces: What are the components? What do I understand? What's unclear? What's one piece I could solve? Then write about how breaking it down helps you solve it.

Think of one dilemma you're working through. Write it down. Then explore: What are my options? What values does each option connect to? What matters most to me? What would each choice mean? Then write about what values guide your choice.

Think of one stuck point you're at. Write it down. Then explore: Why am I stuck? What have I tried? What haven't I tried? What would someone else see? What's a completely different approach? Then write about what perspectives would help you move forward.

Think of one solution you're exploring. Write it down. Then create a test plan: What would I try? How would I know if it works? What would success look like? How long would I test it? Then write about how you can test this solution.

Think of one way forward you're considering. Write it down. Then break it into steps: What's the first step? What's the second? What comes after? What do I need for each step? Then write about what steps you can take to move in that direction.