“I would rather have questions that can't be answered than answers that can't be questioned.” ―Richard Feynman

"In all affairs it's a healthy thing now and then to hang a question mark on the things you have long taken for granted." ―Bertrand Russell

“To ask the 'right' question is far more important than to receive the answer. The solution of a problem lies in the understanding of the problem; the answer is not outside the problem, it is in the problem.” ―Jiddu Krishnamurti

Useful questions:

  • When facing a tough situation (or dealing with sunk cost) use the wise outsider question:

    • Imagine a wise outsider has come to make a decision for you (not burden with the baggage, the cost, the backstory). What would he do?

    • Andy Grove: if we got kicked out, what would our successor do?

  • To be more productive: "What one task can I do now that will make the rest irrelevant or easy?"

  • Avoiding confirmation bias: "Under what conditions would my idea be a bad idea?"

  • Gaining claritiy: "What is the real truth of the situation that is not yet obvious to me?"

  • When you want different results (in life/business/etc) than everyone else, ask questions no one else has the courage or will to ask.

    • "What is currently not possible in my life/industry that if it was possible, would change the game?"

  • "What would your life look like if you measured every decision you made against your future vision?"

  • “What does it mean?” is often impractical. It's better to ask:

    • "How can I use it?"

    • "What can I learn from this?"

  • What is working and what could be working:

    • "What brings me satisfaction in my life? How can I do more of it?"

    • "What could I be happy about?"

  • When a question triggers anxiety or fear, ask kaizen questions - small, gentle, action-oriented questions:

    • When you are trying to reach a goal, ask yourself every day: "What is one small step I could take toward reaching my goal?"

    • After Epictetus: What is it I want that is not within my power?

    • When you are unhappy but aren't sure why: "If I were guaranteed not to fail, what would I be doing differently?"

  • When stuck on something challenging: What might it look like if it was easy?

  • "Via Negativa" questions like:

    • What kind of person I don't want to be?

    • What is my not-to-do list for today?

  • To avoid survivorship bias when presented with a new statistic, inference, assessment, ask:

    • What's the process that generated that data?

    • What are the things that could have happened that might have led them to not measure something?

    • What's the data that's not present?

  • The Hamming Question: What are the most important problems in your field, and why aren’t you working on them?

The question you most often ask yourself (or others ask you) can either guide or control you:

"If they can get you asking the wrong questions, they don't have to worry about the answers." ―Thomas Pynchon

Seeking the right questions beats seeking answers. Answers are fragile. Questions forge a path. Answers can lead you astray.

"The right question at the right time can change the course of a life, can still a turbulent mind, or heal an angry heart." ―Ryan Holiday

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