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Weigh Pros & Cons

When to use this

You're sitting with a decision and can't see it clearly. Maybe you're too close to it, or the upsides and downsides are all mixed together in your head. A few seconds with this prompt cuts through the noise.

The prompt

You are a balanced thinking partner. I'm weighing a decision and need a clear pros-and-cons breakdown.

The decision: [DESCRIBE WHAT YOU'RE CONSIDERING — e.g. "whether to accept a job offer that pays more but requires relocating"]

Context that matters: [SHARE RELEVANT DETAILS — e.g. "I have a young family, own my home, and value stability. The new role is a step up in seniority."]

Please give me:
1. A pros list (genuine upsides, not just surface ones)
2. A cons list (genuine downsides, including ones I might be avoiding)
3. One or two tensions — trade-offs where a pro and a con are in direct conflict
4. One question I should answer before deciding

Keep it honest and don't try to make one side look better than the other.

Before and after

Before — what you bring to the prompt:

  • Deciding whether to go freelance after 8 years at the same company
  • Context: steady income matters, but I've been bored for two years; I have savings; no dependents

After — what the AI returns (excerpt):

Pros - Control over your schedule and the work you take on - Higher earning potential once you build a client base - Two years of boredom suggests real alignment risk staying put

Cons - Income becomes variable — feast-and-famine cycles are common early on - You lose institutional knowledge, team, and the low-stakes safety net - Benefits (health, retirement) require active management

Tensions - The same savings that give you a runway also make the status quo feel safe enough to stay — that comfort may delay a decision you'd eventually regret.

Question to answer first - Do you have one or two clients you could approach before you give notice?

Make it yours

  • Ask the AI to weight each item (High / Medium / Low) based on your stated priorities.
  • Add "Now give me the counterargument to each pro" for a stress test.
  • If you already know which way you're leaning, say so and ask the AI to push back.
  • Ask for a "one year from now" framing: "Which regret would sting more?"

Watch out for

AI is good at surfacing considerations you've suppressed, but it doesn't know your life. The cons list may feel impersonal. Push back if something doesn't fit your situation, and treat the output as a starting point for your own thinking, not a verdict.