How to tell if you're asking the right question

Not knowing the answer can feel unsettling, but what if uncertainty was actually something to embrace? In this episode, Michael sits down with Elizabeth Weingarten to explore that idea. Elizabeth, whose work spans top publications and research programs, shares insights from her book How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty. Their conversation unpacks why we often resist uncertainty and how curiosity, community, and authenticity can transform the way we approach life’s biggest unknowns. She also reflects on the role of genuine self-expression in relationships, inviting listeners to see how asking better questions might open the door to a more fulfilling life.

Listen and Learn: 

• Why certain uncertainties unsettle us most, and how our brains and biology shape our struggle to live with the unknown
• Elizabeth’s powerful "question tree" metaphor that categorizes the types of questions we ask in life, from quick-answer "peach" questions to lifelong "heartwood" questions, and how letting go of "dead leaf" questions helps us grow
• How our search for quick answers can keep us stuck in uncertainty—and why learning to sit with unanswerable questions and ask better ones is key to real growth and self-understanding
• Embracing open-ended questions instead of binary ones for deeper self-understanding, growth, and freedom from the need for control
• What it truly means to “live” and “love” life’s big questions, moving beyond the shallow advice to “embrace uncertainty” and instead learning how our questions can guide growth, clarity, and connection to our future selves
• Recognizing and refining the right questions in your life, ones that lead you back to your values, open new possibilities, and move you forward instead of getting stuck in fear, “shoulds,” or rumination

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Resources: 

• Elizabeth’s Book, How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty: https://bookshop.org/a/30734/9780063335134
• Elizabeth’s Website: www.elizabethweingarten.com
• Elizabeth’s Substack: Time Travel for Beginners
• Yael’s Article: How Practical Wisdom Helps Us Cope with Radical Uncertainty (By Yael Schonbrun and Barry Schwartz)

About Elizabeth Weingarten

Elizabeth Weingarten is a journalist and applied behavioral scientist who works at the intersection of science and storytelling. She has been part of the editorial staffs of The Atlantic, Slate, and Qatar Today, and also served as managing editor of Behavioral Scientist. Her writing has appeared in outlets including The Atlantic, Slate, CNN, Financial Times, Harvard Business Review, and TIME. Beyond journalism, she has led research programs at the think tank New America, the consultancy ideas42, and the tech companies Torch and Udemy. Elizabeth lives in Northern California with her husband and son. You can learn more about her work at www.elizabethweingarten.com.

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