In this powerful episode of Passion Struck, John R. Miles is joined by journalist and applied behavioral scientist Elizabeth Weingarten, author of How to Fall in Love with Questions. Together, they explore the transformative potential of living with uncertainty — and why our biggest, most uncomfortable questions might be our most valuable teachers.
Drawing on insights from her own life, cutting-edge research, and the timeless wisdom of Rainer Maria Rilke, Elizabeth argues that our culture’s obsession with easy answers is failing us. Instead of avoiding uncertainty, she encourages us to embrace it — not just intellectually, but emotionally and behaviorally.
What if the most powerful tool for bridging divides isn’t a better argument, but a better question?
In a time when certainty is idolized and moral clarity often masquerades as moral superiority, Elizabeth Weingarten invites us to reconsider the role of questions in our lives. On this episode of the Passion Struck podcast, we explore how falling in love with questions — rather than rushing toward answers — can reshape the way we engage with the world and with ourselves.
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Introducing The Ignition Room
Last week, we officially introduced The Listening Room—a dedicated community platform for Passion Struck listeners and supporters. It’s designed to deepen audience engagement around the podcast and provide a space for more meaningful interaction beyond the episodes.
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“A powerful question can change a life — because it changes the way we think about our stories, our struggles, and our strengths.”
Elizabeth Weingarten
In case you didn’t already know it, John R. Miles (@John_R_Miles) takes your comments and questions for Momentum Friday right here every week! If you want him to answer your question, register your feedback, or tell your story on one of our upcoming weekly Momentum Friday episodes, drop us a line at [email protected]. Now, let’s dive in!
Listen to the episode on Apple Podcasts, Spotify, Podcast Addict, Pocket Casts, Stitcher, Castbox, Google Podcasts, Listen Notes, Amazon Music, or on your favorite podcast platform. You can watch the interview on YouTube below.
Unlock the Power of Asking Better Questions with Elizabeth Weingarten
In this enriching conversation, John R. Miles speaks with Elizabeth Weingarten, a leading voice at the intersection of behavioral science and human connection. Together, they delve into the practice of asking deeper, more meaningful questions—not as a means of control, but as a pathway to self-awareness, empathy, and resilience. Elizabeth shares the pivotal moments and personal stories that have shaped her perspective, and how working with researchers and thought leaders helped her understand the role of inquiry in thriving through complexity. Whether you’re navigating change, leading a team, or simply trying to become a better listener, this episode offers a transformative lens on the art of thoughtful questioning.
Key Takeaways from This Episode with Elizabeth Weingarten:
- Reframe uncertainty as an opportunity to grow, rather than a threat to avoid.
- Ask questions that invite reflection, not just answers—especially in relationships and leadership.
- Learn to pause and observe before reacting, and let curiosity lead in difficult moments.
- Shift from problem-solving to sense-making, especially when navigating emotional or ambiguous situations.
- Discover how silence and space in conversations can foster deeper understanding.
- Explore how behavioral science can offer practical tools to rewire how we handle doubt and discomfort.
WHY IS THIS EPISODE WITH ELIZABETH WEINGARTEN A MUST-LISTEN?
This episode goes far beyond the typical conversation about personal growth. Elizabeth Weingarten challenges us to see questions not as a sign of weakness, but as a superpower—especially in uncertain times. Her insights blend real-life vulnerability, scientific wisdom, and practical tools that will change how you think, speak, and lead. Whether you’re looking for clarity in your life or connection in your relationships, this episode is an empowering invitation to pause and start asking better questions.
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STARTER PACKS
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How Asking the Right Questions Can Help You Thrive in Uncertainty
In this inspiring Passion Struck interview, Elizabeth Weingarten explained how embracing uncertainty begins with something deceptively simple: learning to ask better questions. Drawing on insights she shares in her book How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty, Elizabeth reframes questions not just as tools for acquiring information, but as essential instruments for growth, connection, and clarity.
During the conversation, she illuminated how our cultural obsession with certainty and quick answers can hinder our ability to sit with ambiguity—something she believes is deeply necessary in today’s complex world. Instead of viewing uncertainty as something to conquer, she encourages a shift: to see it as fertile ground for insight, creativity, and emotional resilience.
Elizabeth also unpacked how questions can act as mirrors, revealing our assumptions, blind spots, and values. When we ask ourselves the right kinds of questions—open-ended, reflective, and nonjudgmental—we create space for deeper self-awareness and more intentional decision-making. She explained that falling in love with questions means letting go of the need to fix, diagnose, or even fully understand, and instead, leaning into the vulnerability of not knowing.
Through personal anecdotes and behaviorally science-backed strategies, she offered practical ways listeners can begin to integrate this mindset into daily life—whether it’s pausing before responding to a challenge, replacing judgment with curiosity in relationships, or navigating change without a rigid roadmap.
Ultimately, Elizabeth made a compelling case for why cultivating a questioning mindset isn’t a weakness—it’s a path to thriving, especially in uncertain times.
What You Will Learn about How to Fall in Love with Questions
Here are six key takeaways from the Passion Struck episode with Elizabeth Weingarten on How to Fall in Love With Questions:
- Uncertainty Isn’t a Problem—It’s a Portal
Life’s hardest questions aren’t meant to be solved immediately. They’re invitations to grow, reflect, and connect with your truest self over time. - Our Obsession With Certainty Can Be Harmful
Fast, tidy answers—especially from influencers or institutions—often suppress deeper truths and can lead us further from what we truly need. - Questions Hold the Key to Meaningful Change
Embracing open-ended inquiry helps us better navigate identity shifts, career transitions, moral dilemmas, and emotional upheaval. - Living in the Question Requires Emotional Stamina
Sitting with not-knowing is psychologically demanding but ultimately expansive. It asks for patience, vulnerability, and a tolerance for ambiguity. - Behavioral Science Supports the Power of Inquiry
Research shows that reflective questioning enhances decision-making, strengthens relationships, and deepens personal resilience. - You Don’t Need to Be an Expert to Explore Your Life
“Question literacy” is a skill we can all build. The most important answers often emerge not from authority, but from curiosity and self-trust.
THANKS, ELIZABETH WEINGARTEN
If you enjoyed this interview with Elizabeth Weingarten, let her know by clicking on the link below and sending her a quick shout on Instagram
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If you want us to answer your questions or you want John to discuss a topic on one of our upcoming Momentum Friday episodes, drop us a line at [email protected].
RESOURCES FROM THE SHOW WITH ELIZABETH WEINGARTEN
Please note that some of the links on this page (books, movies, music, etc.) lead to affiliate programs for which The Passion Struck podcast receives compensation. It’s just one of the ways we keep the lights on around here. Thank you so much for being so supportive!
- Elizabet Weingarten’s Website
- Elizabeth Weingarten’s Linkedin
- BUY Elizabeth Weingarten’s Book ‘How to Fall in Love with Questions’
- Passion Struck Core Value System: https://passionstruck.com/the-passion-struck-core-belief-system/
- Listen to Passion Struck’s interviews with New York Times bestselling authors Gretchen Rubin and Seth Godin.
- Check out Passion Struck’s Episode Starter Packs on Spotify or Passion Struck starter packs to get started with the podcast.
My solo episode on The Mattering Mindset in Love – Choose the Love You Deserve
Can’t miss my episode with Topaz Adizes on Asking Better Questions Is the Key to Love
Listen to my interview with Alison Wood Brooks on How to Make Every Conversation Matter
My episode with The Art of Listening: How to Make People Feel Like They Matter
Catch my interview with Charles Duhigg on the Hidden Power of Supercommunicators
About Today’s Guest, Elizabeth Weingarten
Elizabeth Weingarten is a renowned writer, speaker, and thought leader at the intersection of behavioral science, curiosity, and personal growth. She is the author of How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty, a groundbreaking book that explores how asking better questions can transform our lives, relationships, and society—especially in moments of doubt and change. Elizabeth currently serves as Head of Behavioral Science Insights at Torch, where she uses science-backed strategies to help individuals and organizations foster growth through meaningful reflection.
Her work has been featured in major publications including The Atlantic, Slate, and The New York Times, and she hosts the podcast Why We Question, which delves into the power of curiosity and how it shapes our world. A former managing editor at behavioral science think tanks and a passionate advocate for inclusive leadership, Elizabeth brings depth, empathy, and intellectual rigor to every conversation she leads.
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