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The Wrong Questions You’re Asking AI

Sent on February 19, 2026

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    Everyone is using AI to think less.

    But the highest-leverage AI prompts do the exact opposite. They make you think more.

    The most common AI prompts make us comfortable:

    • “Summarize this article.”
    • “Write this email for me.”
    • “Tell my girlfriend it’s over.”

    But, the best prompts force you into discomfort.

    Here’s what I mean.

    This prompt went viral last year:
    “Based on everything you know about me, what are my biggest blindspots?”

    Decent.

    But watch what happens when you engineer psychological pressure into the structure:

    ROLE: You are an expert psychologist with a keen eye for spotting human patterns.

    OBJECTIVE: Based on everything you know about me, what are my biggest blindspots? How are they holding me back? What potential am I wasting? What should I be paying attention to but I’m not?

    INSTRUCTIONS:
    – Reason from first principles
    – Do not make large leaps—stick to what’s most likely
    – Go deep, don’t hold back
    – Be brutally honest

    OUTPUT:
    1. Summary: 3–5 sentences describing my patterns
    2. Top 3 Blindspots with:
    – Current belief
    – Why it’s flawed
    – Harm pattern (how it shows up)
    – Upgraded belief (clear, testable)
    – One micro-experiment to validate the new belief
    3. Next 14 Days: One behavioral test I can apply

    TONE: Curious, incisive, non-judgmental. Challenge assumptions without shaming.

    Here’s what just happened:

    → “Be brutally honest” strips politeness filters.
    → “First principles” blocks generic BS.
    → “Upgraded belief + micro-test” forces action.
    → “Next 14 days” removes the “someday” excuse.

    People won’t shut up about optimizing prompts for clarity, when really they should be optimizing for inescapability.

    We’ve democratized access to world-class coaching—
    And most people are using it to write breakup emails.

    If your AI conversations don’t occasionally make you uncomfortable…
    You’re just having a very expensive echo chamber conversation.

    See you Monday,
    Mark Manson

    #1 New York Times Bestselling Author
    My Website – My Books – My YouTube Channel – My Podcast – My Community