“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?"

    • 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 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