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

0:00Coming up next on PassionStruck. 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.

0:44Welcome to PassionStruck. 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.

1:23Now, let's go out there and become PassionStruck. Welcome to PassionStruck, 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.

1:57We 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. PassionStruck was just named the number three life leadership podcast by 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.

2:32Now, 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 in behavioral scientist. She's led research at North America, Ideas 42, 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.

3:15In 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. And if you're just discovering the podcast, check out our episode starter packs at either Spotify or passionstruck.com slash starter packs curated playlists to help you dive deeper into themes like mindset, leadership, purpose, and emotional mastery.

3:52And if you're interested in watching these instead of listening to them, we have two YouTube channels, one at John R. Miles and also a Clips 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.

4:29I am absolutely thrilled today to welcome Elizabeth Weingarten to PassionStruck. Welcome, Elizabeth. Thank you so much, John. It's great to be here. 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 has it always been Elizabeth? 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.

5:08So 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. 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? Yes. So exactly as you said, I grew up with actually two parents who are journalists. And at night at dinner, my dad would both recount the exciting experience he had as a journalist at work that day.

5:56And 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 changes. So my dad became a journalist in the 1970s, a heyday of journalism. And think about kind of the Watergate scandal, Woodward and Bernstein, right? These kind of golden days of investigative journalism.

6:37And 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 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.

7:18Fundamentally, 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 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.

8:03But 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 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?

8:45This 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. 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 that this was in the early days. And I was talking to this former SEAL, Mark Define, and we were having the same type of conversation.

9:28And he had started out working for Deloitte & 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 Marshall art 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. I'm so glad to hear it.

10:11And that is, you articulated so much of what the book aims to express and talk about. 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. 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?

10:54Because 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 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 had for writing the book emerged during a time in my life when I was buckling under really heavy questions.

11:31These 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 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 Rilke and a 19-year-old aspiring poet by the name of Franz Kappes.

12:16It'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, 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.

13:09And 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. 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.

13:52And 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, 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.

14:33A 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. 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.

15:16Part 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 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.

15:55Absolutely. 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 on every page, the best book ever written about behavior science and discrimination.

16:44What 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.

17:35And it was one of those situations where I had been, 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 in terms of, in behavioral science, we talk a lot about context matters, right?

18:17And 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 Eris 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.

18:55And this book came at the right time to really change the way that I saw how I could address those challenges and made me want to pursue that in my own career. 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 behavioral scientists who were examining all these reports that were coming out of SAS and micro strategy and trying to understand what made customers tick.

19:48And we were very good at it because I think at that time in 2005, 2006, 2007, Lowe's was really ahead of the curve on 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 Yadin, and David says, John, neuroscience is going to work for people, but it's going to take significantly longer to impact change.

20:35What 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. 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 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 there's endless learning because we humans are strange and complicated individuals.

21:18So always something to learn in the behavioral science field. 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 scientists to Charles Duhigg and Andy 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.

22:02And I found myself as the editor-in-chief of this publication called Bold Business, 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 long way of wanting to ask you this question, you must have covered a ton of different interesting topics at Behavioral Scientist.

22:45Is there one that really stood out for you as unique or that really piqued your interest? 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, D.C.

23:30And I was going on all these dates with men and was having this experience where the 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 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.

24:12And that's a topic that I do pick up in the book as well. But one of the pieces that I wrote for behavioral scientists 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. A lot of the research that's been done is in academic settings. 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.

24:55And so the question that researchers were 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 scientists that continues to be really intriguing and important to me is this question of technology addiction. And 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.

25:36And that was also an audio piece that I recorded. I really enjoyed those two topics in particular come to mind. 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 a hundred 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? 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.

26:32And 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 of 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, 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.

27:12And 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 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.

27:50I 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 this 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, I was questioning about whether or not we should stay married, what I was doing with my life, whether I'd ever have the success as a creative person that I was craving.