Elizabeth Weingarten on How to Fall in Love With Questions | EP 605

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/PASSIONFor 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

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

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• 0:30John R. Miles?

  Coming up next on Passion Struck.

• 0:32Speaker 02

  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.

• 1:14John R. Miles?

  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.

• 1:57John R. Miles?

  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.

• 2:42John R. Miles?

  Passion Struck was just named the number three life leadership podcast by Million Podcasts, standing proudly alongside shows like The Jaco 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.

• 3:24John R. Miles?

  Elizabeth is a journalist and applied behavioral scientist, whose work has appeared in The Atlantic, Slate, and Behavioral Scientist. She's led research at North America, Ideas42, Udemy, and Torch. And now she's the author of How to Fall in Love with Questions, a bold, paradigm-shifting book that invites us to rethink our relationship with uncertainty. In today's episode, we unpack why our brains crave closure and why that craving often leads us astray. How embracing curiosity can foster resilience, creativity, and deeper connection. What it means to live the questions and how that mindset can shift everything. Elizabeth offers a fresh, compassionate, and practical roadmap for anyone wrestling with indecision, ambiguity, or the pressure to have it all figured out.

• 4:09John R. Miles?

  And if you're just discovering the podcast, check out our episode starter packs at either Spotify or passionstruck.com/starterpacks, curated playlists to help you dive deeper into themes like mindset. Leadership, purpose, and emotional mastery. And if you're interested in watching these instead of listening to them, we have two YouTube channels, one at John R. Miles and also Eclipse channel at Passion Struck Clips. Go check them out and subscribe. Now get ready for a perspective shifting conversation on how to rethink uncertainty, unlock your growth, and yes, fall in love with life's most powerful questions. Here's my conversation with the brilliant Elizabeth Weingarten. Thank you for choosing Passion Struck and choosing me to be your host and guide on your journey to creating an intentional life. Now let that journey begin.

• 4:59John R. Miles?

  I am absolutely thrilled today to welcome Elizabeth Weingarten to Passion Struck. Welcome, Elizabeth.

• 5:05Speaker 02

  Thank you so much, John. It's great to be here.

• 5:08John R. Miles?

  Well, I always love interviewing Elizabeth because it's my mom's name, although everyone knows her as Betty. Did you have a shorter name growing up? Or Elizabeth? It's always been Elizabeth.

• 5:20Speaker 02

  I love that. I have had many nicknames in my life, having a very long name like Elizabeth Weingarten, you have to expect that. But different people in different parts of my life have given me different nicknames. My high school friends used to call me Dubs and my college friends called me Eliz. So I've never had like traditional Elizabeth nicknames. I've never really been a Liz or a Lizzie or a Betsy. But yeah, people choose more eccentric nicknames for me in my experience.

• 5:52John R. Miles?

  As I was doing research on you, I heard you tell this story that when you were growing up, your dad used to tell you quite frequently, whatever you don't become a journalist. And in fact, that's what you ended up studying. Can you share a little bit more about that journey?

• 6:09Speaker 02

  Yes. So exactly as you said, I grew up with actually two parents who were journalists. And at night at dinner, my dad would both recount the exciting experience he had as a journalist at work that day. And so I was hearing and seeing how much he loved. His job. And at the same time, I think the challenge for him was feeling like, well, journalism was so meaningful and satisfying to him, but it wasn't the most financially lucrative job in the world. And so I think what he was getting at was he wanted me to find some financial stability. And this was also a time that journalism was undergoing really significant

• 6:54Speaker 02

  changes. So my dad became a journalist in the 1970s, the heyday of journalism. And to think about kind of the Watergate scandal, Woodward and Bernstein, right? These kind of golden days of investigative journalism. And so when I was growing up in the, or when he was having these conversations with me in the early 2000s, this was a time that the internet was coming. People didn't really know how it was going to shape media. It was already starting to change media quite a bit. And he saw that this was maybe not the most stable career path in the world. And so that was what he was trying to impart to me. But unfortunately, I loved it. I loved the

• 7:35Speaker 02

  experience of interviewing people, of starting out not knowing anything about a topic and a few having the excuse to call up people from all different kind of walks of life and to learn from them. Fundamentally, that's the thing that has always really excited me and interested me about journalism is you just get to talk to the most interesting people and you get an excuse to do that. In high school, I was the editor of the paper and that was really my passion. And then I ended up studying journalism in school and college and started out more traditionally in journalistic organizations. So I worked at The Atlantic and Slate. But over time, I

• 8:15Speaker 02

  found myself interested in journalism and other subjects and wanting to navigate a career where I could use my journalism skills to explore, for instance, kind of policy and eventually behavioral science, which we'll talk about. But I think I've really worked now at the intersection of science and storytelling, doing journalism. And applied behavioral science research everywhere from these traditional media outlets to the think tank New America, to the applied behavioral science firm Ideas 42, and now in the tech world. And I think maybe another way to wrap up this career path is by sharing some

• 8:57Speaker 02

  of the questions that have really motivated me throughout my career. So questions like, why do we humans do the strange things we do? How can we change our behavior to benefit ourselves and those around us? And how through a deeper understanding of psychology can we all live more meaningful lives? Journalism has really given me a lens through which to understand the world and ask questions and has guided me to some of these other passions that have now really informed where my career is at this moment.

• 9:30John R. Miles?

  And we're going to be discussing here in a couple of questions, your new book, How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty, which you just set up by asking those questions. I love this concept of falling in love with the questions. And I remember I was doing this interview on the podcast, this was in the early days, and I was talking to this former SEAL, Mark Divine, and we were having the same type of conversation. And he had started out working for Deloitte and Touche and was in the middle of getting a master's degree when he started to have extra time and he started to go to martial

• 10:10John R. Miles?

  arts classes and mindfulness questions. And one of the things that one of his mindfulness teachers told him was that your life is all about asking the right questions and that you need to constantly challenge yourself over your life with those questions, because that's how you find meaning and purpose, and that's how you find your values and your intrinsic motivation and other things. So I love this topic.

• 10:40Speaker 02

  I'm so glad to hear it. And that is you articulated so much of what the book aims to express and talk about.

• 10:47John R. Miles?

  You really, since we're right here, I'm going to go into it and then I'm going to come back. In the book, you are really challenging the way that we approach uncertainty. What's the central idea behind that approach? And why did you feel it was so important to write the book now?

• 11:04Speaker 02

  Absolutely. So to take a step back here, as you said, the book is really all about how we can develop a different and healthier relationship with the uncertainty in our lives and with these kind of big questions in our lives. And I'll pause for a moment to just really clarify, what are the questions that we're talking about? Because questions are such a big topic, and it can be everything from what am I going to 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

• 11:46Speaker 02

  that you're not going to find answers to in a Google search, right? And the book really, the idea for the book and the passion that I have 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 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

• 12:30Speaker 02

  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 Austrian poet Rainier Maria Wilka and a 19 year old aspiring poet by the name of Franz Kappas. 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 Kappas, this aspiring poet, is asking Rilke,

• 13:14Speaker 02

  who, he's 27 at the time when he's writing to him. Kappas 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 Kappas 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 Kappas 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.

• 13:59Speaker 02

  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. And I wrote it because when I was facing down this really painful uncertainty in my life, I was craving a guide to help me navigate it. Not someone or something to give me the answers necessarily,

• 14:44Speaker 02

  but to help me understand the experience better and to share wisdom from folks who had been there and come through it. To research this book, interviewed scientists, artists, religious scholars, historians, philosophers, talked to a professor with a mysterious illness who devoted her life to figuring out how to live better in uncertainty, a woman who was paralyzed in a car accident, who was rediscovering her identity, the grandson of a very famous public figure, who was determining how to live his life and who he was outside of that shadow of fame, renowned teachers of Zen Buddhism, psychedelic therapy researchers, so many more.

• 15:21Speaker 02

  And I'll just say, finally, just to give folks a sense of how this journey unfolds, divided the book into three big parts. So part one is all about how the search for easy answers can fail us. And we look at why we crave certainty, how our current culture has exacerbated our desire for certainty, and how it really hurts our minds, our bodies, and societies. Part two is all about the rewards of committing to our questions and curiosity. And that's where I'm sharing a lot of stories of folks who show us what are the benefits of being able to live and love the questions, and how did their lives transform when they

• 16:01Speaker 02

  changed their relationships to uncertainty. And finally, in part three, talking about how to start your own questions practice, ways to begin living and loving questions yourself. And that's where we get into some evidence-backed tools to develop that practice and to help navigate your own experience in uncertainty. So I'll pause there. I'm sure we'll chat about many different parts of that.

• 16:25John R. Miles?

  Absolutely. Thank you for going through that structure, because I think it's good for giving 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 in every page, the

• 17:09John R. Miles?

  best book ever written about behavior science and discrimination." What was so meaningful about that book that it changed so much for you?

• 17:20Speaker 02

  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, I 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 under-reported 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.

• 18:05Speaker 02

  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, 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 in terms of, in behavioral science, we talk a lot about

• 18:45Speaker 02

  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 Iris 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. And this book came at the right time to really change the way

• 19:29Speaker 02

  that I saw how I could address those challenges and made me want to pursue that in my own career.

• 19:37John R. Miles?

  So interesting. I really got into behavior science from two different perspectives. One, when I was with Lowe's, I was over all of our big data and all the software developers. And I was working very closely on really getting into metadata and what is driving our products, our customers, et cetera. And specifically for the customer side, we had a whole team. I say team, it was like three or four data scientists who were all behavior scientists, who were examining all these reports that were coming out of SAS and MicroStrategy, and trying to understand what made customers tick. And we were very good at it because I think

• 20:20John R. Miles?

  at that time in 2005, 2006, 2007, Lowe's was really ahead of the curve on and out analyzing that. And then when it came to understanding this on a more personal level, I was really trying to figure out, how do you get people to change? What makes people go from being stuck to unstuck? And I started going down the path of really getting into neuroscience. And so I was studying Andrew Newberg and Vago and a bunch of neuroscientists, Jay Lombard and a few others. I remember I was talking to neuroscientist David Yaden. And David says, John, neuroscience is going to work for people, but it's going to take significantly longer to impact change.

• 21:05John R. Miles?

  What really is going to impact quicker change is behavior science. And so that really clicked for me and has really been where my focus has been over the past five years, really learning as much as I can about all different elements of it. So just thought I'd share that as well.

• 21:24Speaker 02

  I love that. It sounds like we had a similar experience there of just something clicking on, right? And all of a sudden you see, oh, this is a, this is a set of tools that can really help me in a way in my work. And once you start learning about it, at least from my experience, it's just the most fascinating world. And it's, it is, and there's endless learning because we humans are strange and complicated individuals. So always something to learn in the behavioral science field.

• 21:52John R. Miles?

  So I'm going to take a detour from the book and then I'll come right back to it. So we've been talking about behavior science here. And one of the positions that you held along the way was managing editor of the publication, Behavior Scientist, a publication I read on a weekly basis. So I was familiar with you long before I had you on the show. But what I love about that platform, it has allowed so many people from Behavior Scientist to Charles Duhigg and Annie Duke to express their opinions on how the science really works. And I took a step into journalism unexpectedly, never thought in a million years I would get into it. And I found myself as the editor in chief of this publication called Bold Business,

• 22:37John R. Miles?

  where by the end of it, I had written probably 400 or 500 articles myself. But similar to your experience, it really started to help me process how do different people think? I got to interview a ton of people and I got to see so many different patterns emerge in what really shapes businesses and what people, well, I guess it would be how people really shape them by the questions that they ask. So a long way of wanting to ask you this question, you must have covered a ton of different, interesting topics at Behavior Scientist. Is there one that really stood out for you as unique or that really piqued your interest?

• 23:22Speaker 02

  Gosh, so many things. And I do have to just give a tip of the hat to Evan Nestorak, who's the editor in chief of Behavioral Scientist. And he, over the years, has just built such a fantastic publication. And so he deserves so much credit for his vision. And it's been so fun to work alongside of him and see that come to life. I would say For me, one of the most fun topics that I got to explore, I'll actually take you back in time a little bit to about 10 years ago, actually, when I was dating in Washington DC. And I was going on all these dates with men and was having this experience where the

• 24:07Speaker 02

  men that I was going on dates with were not asking me a single question the entire date. And at first I thought, is this me? What's going on here? And eventually I became really curious about what was happening. And it led me to do a lot of reporting about if there were any type of kind of gender or sex differences in question asking, particularly in romantic contexts. And I ended up writing about that for quartz. And indeed, there are. But that really set me on the path to being very curious about question asking and identity. And that's a topic that I do pick up in the book as well. But one of

• 24:46Speaker 02

  the pieces that I wrote for Behavioral Scientist was all about question asking behavior in different contexts. And really looked at, what does it mean when we do or don't ask questions? In a lot of the research that's been done is in academic settings. And so it's really about understanding if you have folks who are, if you, let me start over, sorry. What the research is trying to understand is, a lot of times in academic environments, women and men would ask questions at different rates, right? And a lot of times, women would not ask questions at the same rate as men. And so the question that researchers were

• 25:28Speaker 02

  asking is, well, why is this happening? And does it matter? What can we learn from question asking behavior? And so that was a really interesting topic for me and something that I explored along the way to writing the book. And I'll also say another thing that, another topic that I explored at Behavioral Scientist that continues to be really intriguing and important to me is this question of technology addiction. And how do we, how do we decouple from our devices and from the often kind of addictive behavior that comes from overuse of our phones? And so that was another fun piece that I got to do. And that was also in an audio piece that I recorded. I really enjoyed those two topics in particular come to mind.

• 26:14John R. Miles?

  Thank you for sharing that. And I'm going to come back to the relationship aspect that you just brought up. So I read a ton of books, probably 100 a year. I have never started an introduction with someone talking about questioning whether they should stay married or not. And what was the reason for you opening the book that way? It obviously was a period of uncertainty for you, but it really is a gripping intro for someone reading the book.

• 26:44Speaker 02

  So I opened the book with this question of whether or not to divorce my husband, because that was one of the biggest personal factors for me that led me to want to write the book in the first place. And I'll just back up a little bit and tell folks what was happening. At that point, where, you know, when the book opens, I'd been with my husband for about five years dating, but we'd officially been married for only a few months. And what was happening at that point was really a confluence of a lot of factors. For years, I'd had doubts about my relationship with him. We loved each other, but we both fundamentally,

• 27:28Speaker 02

  we expressed care in different ways. And to me, care was all about validation. To him, care was about critical exploration. And that difference for us led to a lot of fighting and hurt on both sides. And at the same time, we had this connection over inquiry and a willingness to explore uncomfortable questions. But that connection unfortunately could also create a lot of tumult and conflict. Part of me thought that getting married would somehow absolve me of the questions I had about our relationship. But unfortunately, it just seemed to amplify those questions. The other thing that was happening at that time and in that

• 28:09Speaker 02

  kind of scene that we drop into in the first part of the book, is I had recently left my job to work on a creative project, but it wasn't panning out. So I was burning through my savings. I was in this place of not knowing what to do next of not Knowing what I was going to do next, I felt deflated that this project hadn't worked out. And at the same time, my husband was, he was working at the startup that was really demanding a lot of his time. And at this basic level, I didn't feel like he was giving me the care I wanted and needed. And he felt the same way. And so it was this perfect storm. And so when I opened up, I was in the book, was questioning about whether or not we should stay married,

• 28:52Speaker 02

  what I was doing with my life, whether I'd ever have the success as a creative person that I was craving. And I just felt crushed under all of that. And it was around that time that I came across Rilke and Letters to a Young Poet and was struck in that moment by how comfortable I felt with uncertainty and questions in my professional life. As we were talking about, this was a topic that was fascinating to me and that I wrote about in Behavioral Scientist, but this comfort with questions completely broke down in my personal life. I, Rilke talks about loving the questions. Well, I had never felt further from loving the questions in my life.

• 29:33Speaker 02

  I hated the questions. I hated these questions about what am I doing with my life? And should I stay married to this person? And so it made me really want to understand what would it look like to change that? And to learn what people were doing who had learned this way of being in the world. So that was really, I wanted readers to experience early on the personal impact and the stakes for me in this journey.

• 30:01John R. Miles?

  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.

• 30:34Speaker 02

  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. 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, it's, 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.

• 31:19Speaker 02

  I don't need to rush to take action on this particular unknown in my life.

• 31:25John R. Miles?

  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, there are good decades and there are 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.

• 31:57Speaker 02

  Oh, absolutely.

• 31:59John R. Miles?

  Yes. So your book has some interesting names in it. Peaches, Papa's, Heartwood, Dead Leaves. What are they all about?

• 32:09Speaker 02

  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, when I, 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 is 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?

• 32:53Speaker 02

  The second category of questions are the paw questions. And this is a fruit that takes a pawpaw tree five to seven years to grow this fruit. And so these are longer term answerable questions. So an example of a question like this might be how you might stay in a relationship if a new fertility treatment will help you get pregnant. You know, these types of questions that might take a little bit longer to answer, but you will still ultimately get an answer to the question. The next layer of questions is the heartwood question. And heartwood is the inner wood of the tree and its purpose is to help with balance, stability and security.

• 33:34Speaker 02

  So heartwood questions are the ones that really stay with you throughout your life. They help you come back to your core sense of equilibrium. And these are the questions like, who am I? How do I live a life of meaning and purpose? And finally, there are questions that don't ripen into answers and we don't ultimately want to love or live or carry with us anymore. And these are the dead leaves, right? These are the questions that we eventually need to release. And these are often questions about past decisions that drive rumination and suffering. Like, why did I break up with this person? Or what would I, what if I had done it differently? And I think the rule here is if a question isn't helping you grow and move forward,

• 34:19Speaker 02

  it may be time to let it go.

• 34:22John R. Miles?

  I want to jump to one of the stories that you share in the book. You talk about a young man at the time named Parker Palmer, who you describe as a golden boy. He attracted powerful mentors. He ends up getting a PhD in sociology in Berkeley. And you describe him as

• 34:43John R. Miles?

  Having this big question hovering over his life, the people who knew him best, his friends and mentors, found different ways to ask him, "What on earth are you doing with your life?" And I know that's a deep question that many of us ponder. Could you perhaps explore his story in more depth and how he came to that answer?

• 35:06Speaker 02

  Absolutely. So Parker is such a special person. He's an educator and activist who has written so many books and has carved out such a wonderful life for himself. But as you were saying, as he was finding his way in his career, he was really struggling under the weight of expectations, right, of his family and friends for him to follow a more traditional path. They really saw him as somebody who was headed for this path of becoming a university professor, pursuing this traditional academic path. But that never felt right to him. And so he was struggling with this question of what are you doing with

• 35:47Speaker 02

  his life? And what are you doing with your life, right? And in part, he was struggling with it because he hadn't yet learned to sit with and explore some of the hidden parts of himself, the parts that didn't conform to the expectations of others. And what I talk about in the book, in Parker's story, is how through a deeper relationship with questions, he used questions as tools, as an internal GPS, to find his way back to himself, what he really wanted, his own evolving truth. And so he really needed to understand

• 36:30Speaker 02

  that before he talked to others about it, before he communicated that truth with other people. But for much of his life, it was really submerged under this sense of, well, this is what I should be doing, and I need to pursue this path that other people think I should. And so the story that I tell is really about how he threw

• 36:53Speaker 02

  Asking different questions and through his own kind of journey of self-discovery, was able to understand the way that those expectations had been guiding him versus his own needs and desires and really understanding how he could let those guide him along that path.

• 37:15John R. Miles?

  So I found it also interesting that you both went to the same high school. Few years apart, but.

• 37:20Speaker 02

  Just a few years.

• 37:23Speaker 02

  About 50 years, I think, apart.

• 37:27John R. Miles?

  So one of the parts of this chapter I really liked is you wrote, just to follow up with what you were just saying. For Palmer, wrestling out loud with honest, open questions became a critical tool in his journey towards psychological well-being. And he ends up saying, is the way you wrote it is, I ended up living some of these questions. They aren't questions you can answer the way you answer a math problem. They are questions you wrap your life around, questions that increase your awareness of how you're living and why. This kind of question is a constant probe into your experience and a way of stirring the pot to see what else is in there.

• 38:08John R. Miles?

  And I brought that up specifically because one of the things that you really go into in the book is the importance of self-awareness. And through all the conversations that I've had on this podcast and interviewing lots of people outside of it, one of the conclusions I have come to is so many of us believe we're self-aware, yet the vast majority of us lack true self-awareness. And it is really the paradox of life. And I know I did personally, and it wasn't until I got an extreme wake-up call and really took about two years asking myself a lot of the difficult questions and really not liking the answers

• 38:52John R. Miles?

  that I made a number of concerted efforts to change how I was living my life. But I think so many people fail to go through exercises like that because let's face it, some of the things you ask yourself when you look in the mirror, you don't answer that's coming back.

• 39:11John R. Miles?

  So what is your advice to someone along these lines of how do you break that pattern? And how do you delve more into that critical self-awareness that we need, not only in our personal lives, but every leader needs it?

• 39:25Speaker 02

  Wow, you articulated something that is so central to the book. And I think the first thing I will say to your point is that kind of journey to self-awareness is really a lifelong one, right? I think we can get better at knowing ourselves. But one of the things that I've found is just it helps to have a sense of kind of humility and also a sense of humor about it, because we're all learning and figuring this out every day. And so it's not necessarily a destination that you reach. And all of a sudden, you figured it out and you know, everything about yourself and you've achieved self-awareness. But a big part of it is almost the recognition that maybe I'll never fully achieve that self-awareness that I so desire. But I'll

• 40:09Speaker 02

  talk a little bit about something practical that I think folks can do. But before that, take a step back, because this kind of relationship with yourself was so central, what I found to this question of how do we live better and differently with uncertainty? And for a long time, I'd imagined that the best analogy for loving and staying committed to a big question was our love for someone else, right? Like a challenging relationship to someone else. But I learned throughout my research and the folks that I spoke to, that instead, the relationship that we have, and this was true for me and true for many people

• 40:51Speaker 02

  that I spoke to. So I'm curious how this will resonate with you and other listeners. But my relationship to my questions was not a reflection of some other kind of relationship to another person. But it was a reflection of my relationship to myself. And that was at the root of being able

• 41:11Speaker 02

  Really exist and sit with uncertainty with more ease and patience. To love the questions, we really first need to learn how to show ourselves more compassion, more love, and to commit to that first. And one of the ways that I found helpful to be able to do that, and one of the kind of tools that I bring up in the book, is the questions map. And the idea there is to share a series of prompts to help folks, not necessarily to find answers to their questions, but to find clarity and to really help guide folks through the flow of different potential questions

• 41:55Speaker 02

  that you can ask yourself, to find your way back to who am I? What do I want? What's maybe making me feel uncomfortable or anxious in this particular period of uncertainty? And so the first part of the questions practice and the questions map is really about curiosity and even becoming aware of and curious of some of the questions that might be behind some of the feelings of anxiousness or discomfort that you might have in a particular moment of transition. And then from there, it's really about, okay, once you have the question, how do you maybe take action on learning about that question? Figuring out what you may already know?

• 42:40Speaker 02

  What types of communities might you be able to rely on to help you get more clarity on that question? And then finally, it's about really coming back and reflecting on what you learned and whether you want to keep holding and living that question, or do you want to let it go? But for me, I've found that is developing that questions practice is a really crucial way of continuing to check in with yourself and deepen your own relationship to what you genuinely want, who you want to become, and is really key to strengthening that sense of integrity.

• 43:24John R. Miles?

  Thank you for sharing that. And I think the questions map is a really good tool that is worth admission for the book, just to use the tool and see how it can help with all the things that you were discussing about self-discovery and what's working in our lives and what's not. So I found it, as I was looking at it, to be something that I wish I had years ago.

• 43:47Speaker 02

  And if it's helpful also for listeners, I can share a story too, that kind of, I think, illustrates what it's like to go through some of the steps on the map. So do you mind if I share? And this is a story that I tell in the book about Tom Rockwell. He's the grandson of the famous artist Norman Rockwell. And Tom, when we meet him, he's really struggling with these questions of who he was, what he was supposed to do with his life. He was in the shadow of his grandfather's fame and even his father's success as an artist. And that shadow was really hanging over him. So he felt this tremendous pressure to contribute something big to the culture, the

• 44:30Speaker 02

  way that they had. And this really led him down this slippery slope of perfectionism, eventually becoming a workaholic. And it was a life that drove wedges between him and the people that he really cared about. Just like you're talking about Parker Palmer, he was trying to live up to a set of expectations for who he was supposed to be, what success meant, how to live his life, rather than exploring, what did those things mean for him? And so he really had to start by becoming aware of some of the questions that were running his life and driving his anxiety. Questions that he described to me as being almost primitive, like, how do I do more?

• 45:13Speaker 02

  How do I be special enough so I don't get in trouble? How do I not be terrified? And from that point, he realized he would need to start asking new questions because those other questions had been really fueling that workaholism. So he started to ask, what is this fear? How do I address it differently? And the fear was that he'd be socially rejected if he didn't work all the time, if he failed to live up to this particular standard. And this is something that I've felt that fear too. And so it really resonated with me. And this was when he Yeah, yeah, I think so many of us. And this was when he started to take action to live out one of his questions and to see what he could learn from that. And the question

• 45:58Speaker 02

  was, what would happen if I didn't work all the time? And so eventually, he found other new questions that he wanted to ask and live, like, how can I help others? But I bring up his story because I think his journey really illustrates a big part of what it can look like to have a questions practice. And it's a journey, again, not to understand necessarily what are the answers, but to clarify things like, what are the questions that are behind the anxiety that I feel? Am I asking the questions that I want to ask? And if I am, what do I already know? How can I find out? Or what might be other or different questions that I want to be guiding my life?

• 46:38John R. Miles?

  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

• 47:20John R. Miles?

  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

• 48:04John R. Miles?

  so many people around the world today are facing?

• 48:07Speaker 02

  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 kind of 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 is, was really, when we think about how, what community did for us

• 48:51Speaker 02

  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 and exist in 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

• 49:32Speaker 02

  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.

• 50:14Speaker 02

  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 these questions that he had, he found relief and kind of solace when he was able to connect with communities of people online, in his case, who were really struggling under similar questions. And so I think questions can be these connections to relationships with people that can or not necessarily going to tell us what is the answer, but can make us feel comforted, supported, and make us feel like we belong during those moments that can be really uncomfortable in our lives.

• 50:58John R. Miles?

  Thank you so much for sharing that. And we've talked a lot today about questions, and I wanted to bring this back to a listener's perspective before we end. There are probably a lot of listeners who feel stuck or overwhelmed by an unanswered question in their life. What's a way that they can begin to reframe it today?

• 51:19Speaker 02

  One of the most powerful ways that I've found to really explore, is this the right question for me? Is, is it a question that you feel opens you up to a wider field of possibilities? Or is it a question that feels like it's limiting you? That's setting you into this binary, this kind of yes or no? And for me, a big example of that was realizing that the question that I was asking at the beginning of the book, should I divorce my husband? Is this the right person to be married to? I had this realization that I talk about in different parts of the book. That question was one that fundamentally wasn't giving me that open space to explore. It was leading me down two paths.

• 52:04Speaker 02

  Yes or no? Should I get a divorce? Yes or no? Right? Neither of those answers felt like the right ones. And so I really had to consider, well, what's a better question? What's a different question? And a better and different question was, well, what would it look like for us to be able to stay together? What would have to change? How would we each need to change in order to make this relationship work? And so I would say a big, kind of a big tool that I found is really supportive. When we're facing that heavy uncertainty is, is this, do I feel like the possibilities are narrowing for me? Or do I feel like this question is opening me up?

• 52:47Speaker 02

  So that's one piece of advice I would share that has been very supportive and helpful for me.

• 52:53John R. Miles?

  Well, thank you so much, Elizabeth, for sharing that. And where can people find out more about you, your book, and how to engage with your work?

• 53:01Speaker 02

  Sure. They can visit ElizabethWeingarten.com. And the book is How to Fall in Love with Questions: A New Way to Thrive in Times of Uncertainty. And you can find links to get it on my website and really anywhere that books are sold. So grateful to you for asking.

• 53:18John R. Miles?

  Elizabeth, thank you so much for being on the show today and congratulations about your new book. It was such a pleasure to have you.

• 53:25Speaker 02

  Thank you so much, John. It was such a lovely conversation. I appreciate all of your thoughtful questions.

• 53:29John R. Miles?

  And that's a wrap on this thought provoking conversation with Elizabeth Weingarten. From reframing uncertainty to embracing curiosity as a path to growth, to the radical idea that living the questions may be more powerful than chasing the answers. Elizabeth reminds us that the unknown isn't something to fear, it's something to befriend. Here are a few key takeaways I invite you to reflect on. Our craving for certainty can often lead us away from the truth, not toward it. Growth begins when we stop demanding clarity and start asking better questions. Curiosity isn't a soft skill, it's a survival strategy. And the most transformative journeys begin not with answers, but with the courage to stay in the discomfort of not knowing. If today's episode spoke to you, I encourage

• 54:13John R. Miles?

  you to pick up Elizabeth's new book, How to Fall in Love with Questions. It's an essential guide for anyone navigating ambiguity in life, work, or relationships. And if you found value in today's episode, consider leaving a five star rating and review on Apple or Spotify. Your feedback helps us grow and bring these powerful ideas to even more people to live with deeper purpose and intention. For show notes, video highlights, and additional resources from today's episode, visit passionstruck.com or head to our YouTube channel at John R. Miles. If you're ready to go further, join the Ignition Room, our private membership community for high performers, or subscribe to The Ignited Life on Substack for weekly tools and reflections I don't share anywhere else. Links to both are in the show notes. Coming up next on Passion Struck, I'm joined by Dr. Andrew Newberg,

• 54:59John R. Miles?

  a pioneer in the field of neurotheology. Together, we'll explore the science of belief, the biology of transcendence, why mattering matters, and how spiritual practices actually reshape the brain. It's a mind expanding episode you don't want to miss.

• 55:13Speaker 03

  If you are part of a religious group that is engaged in a ritual, it could be a ceremony, it could be a meditation practice, prayer program, then you have a whole bunch of people whose parietal lobes are now quieting down. And as they engage this practice, that boundary between themselves and the other people that are with them begins to go away. They begin to feel blended, connected, again, unified, different words that people use, but a sense of oneness with the individuals, with the other individuals that are part of this process.

• 55:47John R. Miles?

  Until then, remember, the courage to question is often the first step to living a life that truly matters. Live boldly, lead with intention, and above all, live life passion-struck.