Passion Struck with John R. Miles
Elizabeth Weingarten on How to Fall in Love With Questions | EP 605
Thu, 01 May 2025
What if the most important thing you could do in moments of confusion, fear, or identity crisis… was to pause and sit with the question, rather than race toward an answer?In a world that values certainty, performance, and instant solutions, Elizabeth Weingarten is offering something rare: a permission slip to not know. On this episode of the Passion Struck podcast, John R. Miles speaks with Elizabeth about her book, How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty, and the profound shift that happens when we stop treating life’s hardest questions like problems to fix — and start treating them like partners in our growth.Click here for the full show notes: Join the Ignition Room!Join the new Passion Struck Community! - The Ignition Room: https://station.page/passionstruckKey Takeaways: 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. For more information on Elizabeth Weingarten: https://www.elizabethweingarten.com/bookSponsors: Factor Meals: http://factormeals.com/factormeals50off and use code “FACTOR MEALS 50 OFF” Rosetta Stone: Unlock 25 languages for life at “ROSETTASTONE.com/passionstruck.” Prolon: Reset your health with 15% off at “ProlonLife.com/passionstruck.” Mint Mobile: Cut your wireless bill to 15 bucks a month at “MINT MOBILE dot com slash PASSION.” Hims: Start your journey to regrowing hair with Hims. Visit hims.com/PASSIONSTRUCK for your free online visit. Quince: Discover luxury at affordable prices with Quince. Enjoy free shipping and 365-day returns at quince.com/PASSION For more information on advertisers and promo codes, visit Passion Struck Deals.Speaking Engagements & WorkshopsAre you looking to inspire your team, organization, or audience to take intentional action in their lives and careers? I’m available for keynote speaking, workshops, and leadership training on topics such as intentional living, resilience, leadership, and personal growth. Let’s work together to create transformational change. Learn more at johnrmiles.com/speaking.Episode Starter PacksWith over 500 episodes, it can be overwhelming to know where to start. We’ve curated Episode Starter Packs based on key themes like leadership, mental health, and personal growth, making it easier for you to dive into the topics you care about. Check them out at passionstruck.com/starterpacks.Catch More of Passion Struck: My solo episode on The Mattering Mindset in Love – Choose the Love You Deserve Can't miss my episode with Jennifer B. Wallace on the Consequences of Prioritizing Achievements Over Mattering My episode with The Art of Listening: How to Make People Feel Like They Matter Catch my interview with Laurie Santos on How to Matter in a Busy World Listen to my solo episode on Fading into Insignificance: The Impact of Un-Mattering in Our Interconnected Era If you liked the show, please leave us a review—it only takes a moment and helps us reach more people! Don’t forget to include your Twitter or Instagram handle so we can thank you personally.How to Connect with John: Connect with John on Twitter at @John_RMiles Follow him on Instagram at @John_R_Miles Subscribe to our main YouTube Channel and to our YouTube Clips Channel For more insights and resources, visit John’s website Want to explore where you stand on the path to becoming Passion Struck? Take our 20-question quiz on Passionstruck.com and find out today!See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Chapter 1: Who are the speakers and what is the purpose of this episode?
Coming up next on Passion Struck.
Chapter 2: What inspired Elizabeth Weingarten to write 'How to Fall in Love with Questions'?
So this book is really an exploration of how to fall in love with the questions of our lives, particularly the ones that can be painful, and especially in a culture in which so many of us have become addicted to fast, easy answers. And I'll say, too, this book is really about my journey to explore this question through science, history, philosophy, poetry, religion, art.
And I wrote it because when I was facing down this really painful uncertainty in my life, I was creating a guide to help me navigate it. Not someone or something to give me the answers, but to help me understand the experience better, to share wisdom from folks who had been there and come through it.
Welcome to passion struck. Hi, I'm your host, John R. Miles. And on the show, we decipher the secrets, tips and guidance of the world's most inspiring people and turn their wisdom into practical advice for you and those around you. Our mission is to help you unlock the power of intentionality so that you can become the best version of yourself.
If you're new to the show, I offer advice and answer listener questions on Fridays. We have long form interviews the rest of the week with guests ranging from astronauts to authors, CEOs, creators, innovators, scientists, military leaders, visionaries, and athletes. Now, let's go out there and become Passion Struck. Welcome to Passion Struck episode 605.
Whether this is your first time joining us or you've been with us on this journey for a while, thank you for being part of a global movement that's all about defying limits, living with intention, and making what truly matters matter most. Before we dive in to today's episode, let's take a quick moment for reflection.
Earlier this week, I had the pleasure of sitting down with Gretchen Rubin in front of a live audience. She's the bestselling author of The Happiness Project and also her new book, Secrets of Adulthood. We explored how small truths, well-timed insights, and the courage to know yourself can shape a wiser, more intentional life. If you missed that conversation, I highly encourage you to go back.
It's one of our most meaningful yet. And I'm thrilled to share some exciting news with you. Passion Struck was just named the number three life leadership podcast by a million podcasts, standing proudly alongside shows like the Jocko Podcast and the School of Greatness. We were also honored with the Gold Stevie Award for Best Independent Podcast at the 2025 American Business Awards.
A huge thank you to all of you who made that possible. Now, let me ask you something. What if not having all the answers was actually your greatest advantage? What if uncertainty wasn't a problem to fix? but a doorway to deeper insight. And what if learning to live the questions could transform how you navigate your biggest life decisions?
These are the powerful ideas we'll explore today with Elizabeth Weingarten. Elizabeth is a journalist and applied behavioral scientist whose work has appeared in the Atlantic, Slate, and Behavioral Scientist.
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Chapter 3: What is the central idea behind embracing uncertainty and living the questions?
Because questions are such a big topic and it can be everything from what am I gonna eat for lunch, right? To who am I?
And those are the types of questions that I'm talking about in this book, these kind of big life questions, questions about purpose, meaning, relationships, identity, the questions that fundamentally don't have fast, easy answers, the questions that you're not gonna find answers to in a Google search, right?
And the book really, the idea for the book and the passion that I had for writing the book emerged during a time in my life when I was buckling under really heavy questions. These were questions about my marriage, my career, and the advice that I found again and again in self-help and pop psychology books was just to embrace uncertainty and
And to me, this felt like a really deeply unhelpful platitude. And luckily, it was around that time that I discovered a much older book that contained what was, for me, a much better piece of advice, if not a more challenging piece of advice. And that book was Letters to a Young Poet. For those who aren't familiar with this book, it's a book of correspondence between the
19-year-old aspiring poet by the name of Franz Kappes. It's from the early 20th century. And it's a book that counts people like Lady Gaga, Dustin Hoffman, Marilyn Monroe among its fans. And Lady Gaga, I learned, even has a line from it tattooed on her. Pretty amazing. The whole book is beautiful. Highly recommend that folks read it. But I was struck by one part of it in particular.
And this is a part where Cappas, this aspiring poet, is asking Rilke, who he's 27 at the time when he's writing to him. Cappas is asking Rilke for all kinds of advice, not only about how to become a poet himself, but how to live his life. And Rilke very famously responds not with an answer,
per se, but by telling Capus how important it is to love the questions themselves as if they were locked rooms or books written in a foreign language. And he also advises Capus not to search for the answers now to his questions, but talks about the importance of living the questions.
But Rilke, in this passage, he never explained what he meant by living the questions now, or even how to think about practically what it means to love the questions. And he also, unfortunately, wasn't talking or thinking about how to do this in a time of AI, Google, smartphones, social media influencers.
So this book is really an exploration of how to fall in love with the questions of our lives, particularly the ones that can be painful, and especially in a culture in which so many of us have become addicted to fast, easy answers. And I'll say too, this book is really about my journey to explore this question through science, history, philosophy, poetry, religion, art.
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Chapter 4: How did Elizabeth's background in journalism and behavioral science shape her perspective?
Absolutely. Thank you for going through that structure because I think it's good for giving people people an idea of what the book is about. And I frame my questions around the different parts of the book. So it'll be a nice segue a little bit later on.
Since you brought up books, another book that I came across through my research that you say helped redefine your path was a book by Iris Bonet called What Works. The subtitle is Gender Equity by Design. And
I've had Cass Sunstein on the show, who's the co-author of Nudge, and he called it a path breaking work packed with insights on every page, the best book ever written about behavior science and discrimination. What was so meaningful about that book that it changed so much for you?
What a great question. So this was indeed the book that made me interested in learning everything I could about behavioral science. And the reason was it was really found this book really at the right time. I was At that time, I was at the think tank New America. I had recently started a policy program focused on global gender equality issues.
And the idea was to do original research and journalism to explore underreported global gender equity issues. And Iris was going to be coming to New America for a panel. And so somebody shared her book with me so I could read about her and her work.
And it was one of those situations where I had been, that the problems and challenges that I had been trying to address through journalism, all of a sudden I saw her writing about those challenges in a totally different way. And introducing me to an entirely different toolkit for addressing particularly gender equity challenges in the workplace.
And so it was just this mind-opening experience of, oh, huh, I had been trying to solve problems with the toolkit that I possessed as a journalist. And here was this totally different way of seeing and framing problems. problems in terms of, in behavioral science, we talk a lot about context matters, right?
And so much of why we do the things we do and our behaviors are a result of our environments and the way in the kind of systems that we interact in. And so this was, at the time, a totally new concept for me and blew my mind. I just had never thought about my own behavior and the world in that way. And Eris just beautifully frames up this challenge.
And I will say that Iris and a friend of mine now, Siri Chalazi, they have a new book out, which is really exciting building on that work. But this was a book that, again, I think I had this personal and professional passion around global gender equality.
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Chapter 5: What role does behavioral science play in understanding human behavior and decision-making?
It made me think that given how many people go through divorces, perhaps more people should be asking the difficult questions, but not just asking them, really thinking through them from the standpoint of what life would look like two, three, four, five, 10 years down the line. depending on how you answer the questions.
Because I would bet more people might stay together if they looked at this over a longer term horizon and they started to choice bracket their decisions.
Well, it's a really interesting point because I think what I was feeling and I think what so many other people feel is it's so uncomfortable to be in that place of uncertainty, right? And so I think what I was craving in that moment was somebody just tell me what to do. Somebody just give me an answer, right?
And I think in these moments of uncertainty, there's really a tendency that we have to want to rush to a fast, easy answer rather than explore and sit with the questions. And I think you can look at it as, yes, this can be a really uncomfortable experience, but In a way, it's also, it can be really freeing to realize and accept that, well, I don't have to have an answer right now.
I don't need to rush to take action on this particular unknown in my life.
I remember years and years ago, I was young and had a, probably a four or five month old and our neighbors had been married for over five decades. And I remember talking to the wife, Karen, one day, and I said what's your advice about
being married and she said well they're good decades and they're bad decades and you've got to weather both of them and i know she wasn't literally saying it was decades any relationship has ups and downs but absolutely yes so your book has some interesting names in it peaches pawpaws heartwood dead leaves what are they all about
Yes. So this is the questions framework that I introduce early on in the book. And the idea is to really help frame up what are the questions that we're talking about here. Again, whenever I bring up the subject of questions, people are like, well, what questions do you mean? And so I liken different types of questions to parts of a fruit tree.
And you can think about the first category of questions as you talk about as peaches, right? These are the short-term answerable questions in your life. Just as peaches ripen quickly on the tree, you can also get answers to these questions on a shorter timeline. So these are questions like, will I get the job? The second category of questions are the paw questions.
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Chapter 6: How does gender influence question-asking behavior in social and academic contexts?
Thank you for sharing that. Elizabeth, we were just talking about the question map. And I thought maybe a good exercise would be to go through a story from the book that illustrates this map in action. Elizabeth, one of the stories that I thought was top of mind for me was the story of Miguel. And I think Miguel's journey is a common one in American history.
In his case, he ended up growing up in Mexico for the first few years of his life before he migrated to the United States and became an immigrant. And he thought that if he studied hard enough, that earning an education would allow him to work through the barriers that he might face going from a lower income growing up to the life that he wanted.
But I think one of the things that is so important here, and it's one of the core areas that I focus on, in fact, I'm writing a whole book on it, is he found himself when he finally started to reach the points that he wanted with his education of not belonging, of feeling isolated, of feeling like he didn't matter.
How do questions, if you're experiencing that, allow you to find meaning, to find a sense of belonging and to work your way out of something that I think so many people around the world today are facing?
I love that question. And one of the big things that I found in my book and in my work is that one of the most fundamental things that we need to be able to sit with our questions to commune with uncertainty is community. And so I do write extensively about lots of different types of communities that can help us exist in uncertainty and have that be sustainable for longer.
And I think one of the things to keep in mind there is that community was really, when we think about what community did for us when we were very early on in human evolution, community was there to help us feel more secure and more stable. And actually people have found that community Being in community reduces the kind of cortisol that we have, makes us feel like we are more stable and secure.
I think what I found too in my work was not only do we need community to be able to sit with an existing questions, but also that questions can connect us to entire communities. And with Miguel and with so many others, he found a lot of comfort connecting with other undocumented immigrants who had faced similar questions in their life, similar experiences of uncertainty.
And it really wasn't about getting answers from those communities. It was about accompanying each other through that uncertainty and kind of witnessing the experience that we have. And that was something that I found that questions could be this portal to belonging and to feeling like you, again, don't necessarily need to
know or find an answer to that question, but questions that connected you with groups of people that were experiencing similar things. And this was something, there was another story that I told in the book of Oliver, who was a guy who was questioning his gender identity and found similarly that
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