Work through a tough decision without going in circles

Stuck between two big life choices? Let the AI help you think it through with questions, pros and cons, and a framework β€” without just telling you what to do.

Getting the hang of it

Copy this prompt

I'm trying to decide between [option A] and [option B]. The situation: [brief context β€” what led to this choice]. What I'm worried about: [your main concerns]. What a good outcome looks like: [what you're hoping for]. Please help me work through this. Start by asking me 5 clarifying questions, then help me weigh the pros and cons. I don't need you to decide for me β€” just help me see it more clearly.

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When to use this

You're facing a big decision β€” stay in your job or leave, move cities or stay put, go back to school or not. You've been turning it over in your head for weeks and keep landing in the same place: nowhere.

Why this works

When we're stuck, we tend to repeat the same few thoughts. The AI breaks that loop by asking questions you haven't considered and framing the choice in a way that separates emotion from logic. It doesn't make the decision for you β€” it helps you think about it more clearly.

Follow-up ideas

  • "What's the worst-case scenario for each option, and how would I handle it?"
  • "If I look back in 5 years, which choice would I regret more?"
  • "Walk me through what the first month would look like for each choice."

Copy the prompt above and paste it into ChatGPT, Claude, or any AI tool. Tweak the words to fit your situation β€” most prompts include follow-up ideas below.