
Journalist and behavioral scientist Elizabeth Weingarten — whose career has taken her from The Atlantic to New America — joins Nicole to unpack the superpower of curiosity, how to build a “questions practice,” and why embracing uncertainty may be the secret to unlocking clarity, confidence, and deeper connection.
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I am Nicole Khalil and you're listening to the this Is Woman's Work podcast. We're together. We're redefining what it means, what it looks and feels like to be doing woman's work in the world today. And in order to redefine something, you've got to get really curious about it. Deeply, wildly curious. In this case, curious about why some things were labeled woman's work and others were not. About the history and the evolution about what you consider doing woman's work and how that might be different from what I consider to be woman's work. I could ask questions about this topic for days. And now I do. But I didn't. Always for a long stretch, let's call it most of my 20s and early 30s, I was much more focused on knowing things than wondering about them. I wasn't so much curious as I was convinced. Convinced I had the answers, busy proving myself tightly gripping to certainty like it was my very special security blanket. But here's what I've learned, especially as a coach and a leader. Curiosity is the power, skill, and asking good questions. That's where the real magic happens. Because when we tell, we're offering our answer. When we ask, we invite theirs. And people don't often take meaningful action from being told. They take action from feeling seen, understood and connected to their own solutions. Now, this hasn't always been easy for me. It still isn't today. I can be a bit of a tell monster because telling feels efficient. And you know, I love me some efficiency, but it's not effective. So I've been on a long, imperfect journey of learning to ask instead of tell asking questions in those moments where I really Want to give advice? Asking instead of assuming. Asking when it's awkward, maybe especially when it's awkward. And let's be honest, culturally, we're kind of terrible at asking good questions. We reward hot takes, extreme opinions and clickbait, not thoughtful inquiry. And none of that is making us better humans. We could all use some practice. So today we're going to do just that. We're going to get curious about why asking questions might be one of the most rebellious and impactful things you can do in a world full of answers. Our guest is Elizabeth Winegarden, a journalist and applied behavioral scientist who's worked everywhere from the Atlantic to Slate. And her new book, how to Fall in Love with Questions, is both a call to curiosity and a toolkit for making it applicable in everyday life. She's challenging the idea of embracing uncertainty and unpacking the dangers of chasing fast, easy answers, the kind that make us vulnerable to what she calls the charlatans of certainty. If that phrase made your ears perk up, same friend, same Elizabeth. Thank you for being our guest. And I think that the best place for us to start is to ask you what made you fall in love with questions? Why you made this your focus of your work?
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Yeah, well, thank you so much for having me and I'm so excited to talk about this. And your intro was just a perfect, I think, encapsulation of not only the experience of kind of curiosity as individuals, but what you laid out in this kind of the society that we're living in and why this can be so, so challenging. But as far as what made me fall in love with questions, I'll back up for a moment and just say too, the book is really about how to get unstuck from. From uncertainty, which is something that I think so many of us have experienced in our lives. And my favorite definition of uncertainty actually is a sense of doubt that stops or delays progress. And so when you kind of think about that, think about that definition of uncertainty, it's an experience that I think so many of us kind of can relate to. Right. That that sense of I don't know what to do next. I have this big question in my life. I don't know how to move forward. And what comes up is, how do I move forward? How do I take action when you don't have all the answers? And so the book is really about that, how do you move forward and how do you take action without having all the answers? In part by forming a different relationship to the big questions of our life. As far as kind of how I got so interested in questions. It actually goes back quite a ways about a decade ago, and I got interested in questions kind of in an unlikely way. I was going on dates in Washington, D.C. and I kept having this experience again and again, going out on dates with men. And the experience that I kept having was that they didn't ask me a single question throughout the whole date. And so I started wondering, you know, is there something about me? Is there something about these guys? What's going on? And as a. And as a journalist, I got really, really curious about what was happening. And it kind of started me on this path to doing a lot of research and writing about questions. And what I discovered, as you said, is questions are kind of this superpower, right? But a superpower that we don't value as a society. Fast forward several years from that time when I was dating, and I had done all of this kind of research and writing about the superpower questions. But I found myself at a time in my life when I was asking myself big questions. And I was kind of in this real season of uncertainty in my life. It was during the pandemic. I had recently gotten married, and I had recently left my job to pursue a new creative project. And both of these things felt like they were failing. And so I was asking myself, should I get a divorce? I was also asking myself, what am I doing with my life? Why did I leave my job? This is really scary. And I was really buckling under the weight of these questions. They were big, heavy questions. And I, as somebody who had done all this writing and research about the power of questions, how great questions were, all I wanted were answers in that moment. But at that time, I came across a book that really changed my life. And I'm sure we'll talk about it a little bit more, but it was called Letters to a Young Poet. I love that book. Yes, it's an amazing book. A book by the poet Rainier Maria Rilke. And it's a book of correspondence between Rilke and this aspiring poet who at the time was 19 years old. He's asking Rilke for all kinds of advice about how to live his life. Um, and Rilke very famously doesn't give him answers. He tells him to, quote, love the questions themselves, as if they were locked rooms or books written in a foreign tongue. And so when I read this passage, I was really struck, because it was beautiful, of course, but it was also striking to me, as somebody who claimed to love questions, was so interested in questions. And yet I Had never felt further away from loving the questions of my life. And so what really kicked this off was my curiosity about, is it possible to love the questions of our life? How do we do it? And how do we do it in a world in which so many of us, as you alluded to, have become kind of addicted to fast, easy answers? And so the book is really a combination of behavioral science and philosophy and history and art, all to answer that central question.
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Okay, there are a lot of things swirling through my brain as you were talking. First. There are so many places where it be has become obvious that we're just not good at asking questions. Right. Like the dating thing. I think every person can relate to that, where it's like, seriously, you don't have a single question for me. But I also think in work environments, like, if I do a seminar or speaking engagement, how often there is space for Q and A and people don't take advantage of it. And I'm always fascinated. I'm like, you don't have a single question about this, you know, big topic or from this person who's on stage who's at least somewhat of an expert on it. I mean, it just. It's very confusing to me. So I guess that leads to the question of, why do you think people are uncomfortable asking questions both internally and also in front of other people? Yeah.
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So it's interesting. When I started doing my research and writing on questions, one of the questions that I was asking was, how do identity and question asking intersect? And so I did a lot of writing on gender, because that was kind of where I started wondering, you know, is this. Is there. Is there a gendered aspect of question asking? And there's some research that suggests there is, and that in. Especially in professional contexts, women tend to ask fewer questions than men. There are all sorts of reasons that you can point to for why that might be. But I think one of the things that we find is that, you know, asking questions, especially in a. In a professional context or in a context where the stakes might be kind of high for you, you want to appear to be a particular way. Asking questions can be a formal vulnerability because you're acknowledging that you don't know something. And as you said, in a world and in a culture in which we are valued for what we know, admitting, hey, I don't know, something can feel. Can feel scary, and. And I think, you know, so there's kind of that aspect of it, and I think it's not. It's not a skill that's taught either. Right. So I think we also aren't kind of trained as, as professionals and as people to, to really kind of dive deeply into the questions of our lives and to be in a space when we're at work to really think, what's a better question that I can ask here versus continuously trying to, to seek the answers.
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Okay. One of the other things that popped up while you were talking about the book is, you know, that it was about getting unstuck from uncertainty. And I think if we read a lot of other books or articles on that topic, a lot of the advice would be taking us toward certainty. Right. Like how to get certain when you are feeling uncertain. Whereas, and you correct me if I'm wrong, my understanding of your work is to love the uncertain parts of your life. That's a great place to ask the questions and sit with the questions and be with the questions versus trying to get out of it so quickly. Is that am I on track? And then my second part is why are we so frickin uncomfortable with uncertainty?
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Yeah, So I think that's exactly right. And I, and I should say there's nothing wrong with searching for answers, but what happens when we, when we feel uncomfortable with uncertainty, particularly about the big questions of our lives? And let me just take a step back here to talk about what type of questions am I really talking about? Because there are questions like what am I having for dinner? And then there are questions like who am I? Or you know, how do I live? Right. I'm moving a purpose. Exactly. And those are the types of questions that it really is going to benefit you to continuously kind of ask and stay curious about and sit a little bit longer in that uncertainty. And that's because when we are, you know, trying to quickly seize on answers, it can make us really vulnerable to the people and industries in our culture that I call the kind of charlatans of certainty. You know, they're everyone from kind of the influencers that you might see and gurus. Right. That, that really claim to have all of the answers for these big meaningful questions in your life. And again, there's kind of nothing wrong, kind of searching for answers and seeking out really trustworthy sources and great coaches and all of these things. But what happens is, I think we get so uncomfortable with uncertainty in our life that we replace reflection and introspection that only we can do with the answers that other people are serving us. So there's nobody who can answer the question for you of what is my purpose? Right. Like that's a question that you need to do the exploration to find out yourself. But it can feel so uncomfortable and that we seek out these other places and these other sources to do that. And so I think there's a real kind of balance that we have to find between kind of searching for. Searching for answers and getting more comfortable kind of in that uncertain place. And one of the things that I recommend in the book and that we can talk about a little bit later, too, is to develop your own questions practice. And I have in the book something called the Questions Map. And it's really designed to help you find clarity in the unknown. So it's not necessarily this is going to give you answers, but it's going to help you in that space where you don't have the answers and you don't know how to move forward. What does it look like to be able to kind of move and do something so you don't just feel like you're stuck, you know, thinking back to that definition of uncertainty, Right. Stopping or kind of delaying your progress. We don't want that. We want to feel like we're kind of moving through our questions and our uncertainty. And so the map and the prompts are really designed to help you do. Do just that.
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It makes me think of being active versus in this uncertainty and sitting with the questions and letting the questions sort of live through us. It's like more of an active process. Whereas when I think of uncertainty, that stops progress. I think of inaction, like we're just stuck. So I'm. I'm thinking out loud. I'm not sure if I'm making the most sense, but to me, it's that feeling of even if it's the smallest step forward, we're in motion, we're active toward asking questions and curiosity.
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Exactly. And I think it really. It starts with, in a lot of cases, just getting curious about what are the big questions in my life right now? And going back to kind of, you know, why we don't ask questions, what's going on? I think so many of us, we don't. We just don't even take, you know, five minutes to sit down and think, what are the big questions that are guiding my life? And often what I've found and what I've found from many of the people that I talk to in the book, and I've talked to everybody from kind of Buddhist, Zen, Buddhist practitioners, to activists, to scientists, to artists. Right. And. And what we often feel is we feel anxiety, we feel worry, we feel fear, and we're feeling these things sometimes every day for, for various people. And a lot of times there's a question that's kind of crouching underneath that feeling, right? You're feeling anxious. And maybe it's because you have this big question about your career, about, you know, being a parent, about a transition that you're going through. Maybe you're, um, you know, trying to, maybe you're, you're, you're, you're retiring or you're entering the workforce or you're becoming a parent or you're losing a parent or, you know, any number of things that can kind of create that sense of, of stuckness, of anxiety, you know, any of these types of challenging emotions. And so often just getting clear on like, what's the uncertainty here? What's the question? That's really kind of the first part of the questions practice and the first part I found to really getting unstuck.
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Okay, I love that. So what is the question, right? What is all of this unearthing or uncovering? If that's step one, I would imagine for many of us, either because we've been socialized to do this or because it's so easily accessible, that the next step is to sort of outsource, right. To leverage experts, books, articles, social media. When we're uncomfortable, it's really easy to want to fix it and it's really easy to go out there and there where these, there are these fast answers or these one size fits all solutions. Now, as you said before, it's not a bad thing to want to find an answer or to get a solution, but I wonder if there's a way of looking at that information differently. So rather than an answer, looking at it as a clue, I'd be like, oh, this might be something that would support me, let's find out. Or like breadcrumbs versus the final destination. And I do worry that that's where we lose a lot of our agency and where we lose a lot of these big questions is we latch so quickly onto somebody else's answer.
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That's exactly right. And I think the way that I would distinguish it, there are a couple of things that you said that I think are totally right on. The way that I would distinguish it is, is it a thought starter or a thought stopper? Right. And so, you know, are you using somebody else's kind of five step process to say, okay, I don't need to think about this anymore, I've got it, I know what my purpose is, or I know who I am, or you know, any of these questions, answers, or is it inviting you into kind of more profound and deeper inquiry? And so I think that's, that's a big part of it to me. And the other part of it is, and part of getting kind of getting clear on what question you're asking is knowing what source to trust for that question. So a big part of the book is, you know, talking about how it's. Again, it's not necessarily, it's not wrong to search for answers, it's not wrong to follow, you know, your favorite influencer. Right. I have many that I think are really smart and interesting people. But it's about knowing which source to trust with a particular question and answer. And I found this out kind of the hard way myself when I write in the book about how when I was going through some struggles in my relationship, I went to an astrologer mostly for what I thought was entertainment. Somebody had gifted me an astrology session. At the time I was very adamant that I did not believe in astrology. I didn't think it was, you know, a science. I was very kind of against the idea that it would. It would tell me anything. And yet I took this question to the astrologer about my relationship, this really important, kind of heartfelt question. And this astrologer told me that she didn't think that my partner was right for me, and she didn't think it was gonna. It was gonna last between us. And this insight that she told me, even though I had said, oh, I don't believe in this. Right. It kind of reverberated throughout kind of my relationship. And I only later talking to another astrologer who was really smart, and I talked to her for the book, Jessica Lanyato. She kind of pointed out to me that I had asked kind of the wrong. I had asked the wrong question of the wrong source. And her analogy, which I think was a really good one, was you wouldn't ask a friend who is always choosing the wrong person for a relationship. You wouldn't ask that friend for relationship advice. Right. And similarly, you need to be really clear about what is the question that I'm asking and what source am I choosing to trust for an answer to this question? And I think so many of us. And I'm going to pick up on a word you use. So many of us kind of give up on our agency, right, when we're searching for answers because we're so, you know, we're so anxious, we're so eager to get out of that discomfort that we're just so seizing on an answer rather than really doing the work to figure out, well, a, what is my question? B, and this is something we can also talk about. Is this the right question? Is this the question I want to be asking and see what are the sources that I want to trust for this? And how do I be really discerning about that?
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Okay. I love the distinction of which source and kind of asking yourself that before you go out there. Like, I think of the example, if I am having some sort of physical ailment, one of my sources might be a nutritionist or a medical doctor, but my source might not be, you know, my hypochondriac friend who minds the Internet for all sorts of information. And I also think I'm curious your thoughts. In most cases, we should be one of the sources. There might be multiple sources, but. But we should be one. I think of your example with the astrologist, it sounds like, and maybe I'm misinterpreting this, that she said something that your inner knowing already believed or knew, which is why maybe it resonated with you. And so sometimes Being open to unlikely sources, but always passing it through you as the primary source. Thoughts?
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Yes, I think. I think you're absolutely right. You always also need to be that source that is determining is this right for me? Is this something that makes sense for my life and for me? When the astrologer said that, it pointed to something, it pointed to the challenges of my relationship in a way that felt really scary because I hadn't fully acknowledged to myself and to those around me kind of what we were going through. And I also. I didn't want to believe it, but I was kind of in this pattern of avoidance about it. I didn't want to. I didn't know what to do. I was. I was feeling stuck, right? And so I didn't. At the same time, I didn't like the way that this particular astrologer told me that it just wasn't going to work out. And so I think what I only realized later was what she told me scared me, but at the same time, I didn't want it to be true. So it confirmed this fear that I had. But ultimately, it was not something that, you know, I wanted the relationship to work out. And so over the course of the book, I talk about my relationship and I talk about how what was really core to shifting my relationship was actually reframing and changing the question that I was asking. And so, you know, early on, I had been asking this question of should I get a divorce? And what I realized was that that question was really limiting in possibilities, right? It's a binary question. And so one of the things that I talk about is, you know, not only identifying your question, but also identifying, is it the right question for you? Is it the question that you want to be asking? And for me, that question and, you know, I probably posed some kind of a binary question to this astrologer, right? Like, should we be together? Or kind of what, you know, some kind of a yes or no. And ultimately, where I ended up was feeling like yes and no weren't good answers for me. Yes, we should get a divorce. I didn't want to get a divorce. And no meant not acknowledging the challenges that we were facing. And so where I ended up was asking a question that was something like, you know, what would it look like for us to stay together? Or how do we both need to change for us to be able to stay in a relationship? And so I think that's really core to this process, too, is figuring out how do we. How do we sometimes change the question and change the frame such that it opens up greater possibilities for our life. And then, you know, to this point about sources, opens up more sources for us to be looking at. And one final thing that I'll say here, too, is that a lot of times when we're feeling stuck in uncertainty and we have this big, heavy question, one of the most significant things that I've found and that I talk about in kind of the four elements of what makes up a great questions practice is the importance of community. So, yes, you know, you can kind of search out these, like, sources, you know, these kind of expert sources. But it can also be really, really helpful to find, you know, friends or family or others in your community who aren't necessarily going to be there to give you the answer because they may not have the answer, but just to go through that uncertainty with you, to kind of accompany you on that journey. So that's a really big part of it, too, is how do you stay comfortable enough kind of in the uncertainty while you're on that journey to find the answer?
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Okay, Elizabeth, I could take this conversation in one million different directions. I want to make sure we talk about a questions practice. I'm wildly curious about these four steps. I had it on my questions list to talk about some tactical tips about asking good questions. You already gave one. Don't have the question be binary. It's not yes or no. Right. Like having a more expansive, open question. Oh, you actually gave a couple, too. And then having that community. I couldn't agree more. Sometimes just having a listener, like, they don't even need to say anything or do anything, just a listener or a witness or a sounding board or whatever you want to call them, sometimes that helps me really get to the better, bigger question that I'm wrestling with. So where should we go here?
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Yeah. Yeah. So I'm happy to share kind of the four elements of a questions practice and share another thing that I learned about what makes for, you know, a really powerful question that you can ask yourself. And I think this also gets to something that we as women tend to, to, to do more of. So I'll, I'll start with the questions practice and then some of the kind of ideas about how to ask their questions. So I mentioned kind of the first part of the questions practice is curiosity, and that's really getting curious about the questions that are guiding your life. Which is easier said than done. Right? Because a lot of times we feel anxious and fearful about some of these big questions. And so again, kind of the, the, the map and the book are really designed to give you prompts and to share stories and ideas to help you get more curious about those questions. So that's kind of step one. Step one is conversation. Conversation. You know, you can think about the questions that we're asking as parts of conversations that we have with ourselves and that we have with others. And so step two is, once you're asking this question, how do you get better at having a conversation with yourself? One thing we know is that during really uncertain times. I don't know about you, Nicole, but I have a tendency, or I've had a tendency to kind of do like an anxiety spiral, right? Like we get in our heads, we're asking this question, or maybe we're just feeling kind of nervous or anxious about the future, and it can not be the most productive conversation that we're having with ourselves. So how do we talk to ourselves differently so that we feel more comfortable in that time of uncertainty?
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I have never spiraled, ever.
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Right.
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Last night.
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Unusual experience. Yeah. The. The third part of a questions practice, as we just brought up, is community. And it's really kind of finding the right relationships and people around you to help you feel safe and secure while you're holding these big questions. And one thing I'll say is that, you know, community really evolved to help us feel more secure. And there is great neuroscience research to show that feeling connected and enmeshed in community actually reduces our cortisol and lights up the parts of our brain that makes us feel like we're getting a reward. The fourth part of the practice is commitment, and that's really about, you know, committing not only to kind of holding onto your questions and exploring them as they evolve throughout your life, but also knowing when to let your questions go. And one of the things that I have in the book is kind of a framework to identify what are the types of questions that we're asking. And I actually liken the questions to parts of a fruit tree. And so the first type of question that you can imagine is like, the peach. And that's a question that you're going to get answers to pretty quickly. Peaches ripen quickly, right? So it's like the will I get the job? Question. The second type of question is the pawpaw question. Pawpaw fruit takes, like, five to seven years to ripen. So maybe you're asking a question about, you know, will I enjoy this new career change? The third type of question, that's your heartwood question. And these are the questions that stay with you across your whole life. So the Questions like, who am I? What is my purpose? And these are kind of. That's the part of the tree that lends its stability and gives it kind of its ability to balance. The fourth part of the questions Tree questions framework are dead leaves. And this is why I bring this up now, because the dead leaves are questions that are no longer serving you. They're kind of keeping you locked in patterns of regret and rumination. It's the why didn't I take that job? Or, you know, what if I had broken up with this person? Or, you know, these, these questions keeping you locked in the past. And so those are the types of questions that sometimes we need to let them go.
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Right?
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Like dead leaves from a tree. And so commitment is both about committing to the kind of the long term of a question, knowing when to let it go. And one of the things that can help a lot with kind of discerning when to do these things is ritual. Right? And one ritual that you can build for yourself is a questions practice. And so those are the kind of four elements of a questions practice. And the final thing that I'll say here about kind of what makes for a great question, in addition to making sure that it's not a binary question, you're also going to want to make sure that your question is serving as a kind of internal gps that it's leading you back to yourself, to what you want to what you need to thrive versus And I've heard you talk about this, Nicole, kind of connecting you back to the expectations that other people might have. Right? So I think sometimes we ask should questions or we ask questions that actually aren't about what we want and what we need, but they're about things that other people have decided that we should want or should need. So really understanding is this a question that comes from. Comes from me. Is it a question that comes from someone else? And how can I make sure that it's a question that is leading me back to myself?
C
Okay, I love everything about that. I'm going to, of course, get your book and go through this myself. And you said at the onset that these are questions that are guiding our lives. And I had the thought that we all have questions that are guiding our lives. It's whether or not we're choosing the questions or being purposeful or asking better questions. I think of, you know, a question that I think was guiding my life for a very, very long time is, am I good enough? Am I worthy? And that's not the question I want to be asking, but it was unconsciously what I was asking myself all the time. And so what kind of was a light bulb moment for me while you were talking is giving ourselves the opportunity to ask better, more meaningful questions as opposed to defaulting to the crap ones that have been fed to us from the shoulds and the supposed tos and all the stuff. Okay, I have 1 million more questions. My last one was around. I'm going to call it back pocket questions. I just have some questions that I like to keep in my back pocket when I don't know what else to say or when I catch myself wanting to default to telling or giving advice. I mean, something as simple as can you tell me more about that? But are there any just good questions that we can keep in our back pocket for ourselves and each other when we want to default to something else?
A
I love that question. And I think I want to reflect just briefly on what you just shared too, about the am I enough? Am I worthy? And just to say that there are several characters and stories that I tell in the book of people who had those same questions and came to the same realization that you did of, wow, I'm asking these questions that are not leading me to a place that I want to go. And so through questions practice, we're able to get back to that place where they, they recognized A, their question and B, that they could ask a different and better question. And that transformed their life in a lot of ways. And, and just to reflect on the right kind of the. Are there different or are there questions that we can keep in our back pocket? You know, I do love. There are a couple of questions that I would point to here. One question that I think can be fun is what would I do if I wasn't afraid? Right. Or if I wasn't afraid of failing? I think that's a question that can kind of open up possibilities for folks. And that's another. That's a big part of you want your question to. In the words of a Zen Buddhist practitioner that I, that I spoke to, Joan Sutherland, a good question should kind of open up the windows and doors in a room, right? So it should really just make your life feel bigger. So that's one. And I think one of the questions that I've been kind of living through my whole life that I think is particularly important for, for folks, especially if you're somebody that has a strong relationship to your career or to your work, is how can we define our worth and value outside of our achievements or accomplishments? So this is one I think that can be really, really hard, especially in our culture, which tends to kind of valorize the things that we can show on our resume. But what does it look like to be able to do that outside side of what somebody can read on your resume? Right. So I think that's a big question that I continue to kind of live. And so I would, I would share those two, but I would be really curious to hear more of your back pocket questions, too.
C
Yeah. So as you were talking, I think probably the biggest back pocket question I use in my day to day life is what would I want jj, my daughter to do in this situation or. Or what, you know, would I hope for her? Because I hope the best for her. Like, I want all the possibilities. I am the most open about what is big and possible when I'm thinking of her. And so if I put it in that lens, then it sort of forces me because I have it in the, you know, this is my opportunity to be an example. And if I want it for her, I should want it for myself. And sometimes that is what opens up the most for me. That. That came to mind. I love that.
A
That's such a. That's such a great one. And now I'm thinking about how I can do that for. With my. With my son, who I also want the best for. And so maybe that'll become one of my back pocket questions.
C
Well, I love that. That would make me very happy. Okay. Well, Elizabeth, I could talk to you all day long and I genuinely have so many more questions, but I am going to immediately, once we stop recording, go get my hands on the book. It's how to Fall in Love with Questions. I know our listeners are going to be all over it, too. And a reminder to those of you listening in, Elizabeth also has a substack, time travel for beginners. Again, I'm going to be subscribing right when we finish here, too. So, Elizabeth, thank you for falling in love with questions and then bringing it to the world. I, for one, am genuinely appreciative.
A
Well, thank you so much for having me and thank you for your very thoughtful questions. It was so much fun to talk to you.
C
My absolute pleasure. All right. I wonder, friend, what would happen if we stopped pretending that we have or always need to have the answer and started getting better at asking really good questions? What if we stopped chasing certainty like it's going to save us and got more comfortable living in wonder in the in between, in the not yet known, where so much more is possible? Today was a reminder for me and hopefully for you, that curiosity isn't just cute or quirky, it's powerful, it's connective, and it's leadership of self and others. And asking good questions isn't a soft skill, it's a smart one and frankly, much harder than just having somebody give you the answer. So I hope this episode invited you to slow down your certainty, challenge your inner tell monster, and fall a little bit more in love with not knowing and being curious. Because sometimes the most honest, brave and world changing thing that you can say isn't I know, it's tell me more. And that is woman's work.
B
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C
Hey girl, this is a legging emergency. My favorite Lululemon leggings, the ones you got me years ago. I think they're lined maybe.
A
Well, I just got back from my.
C
Trip and I think I left them.
A
At the B and B. Girl, I need to replace these.
C
Could you send me the link to where you got them? I need a pair asap. Also, my birthday's coming up, so. Anyways, thanks girl. Talk soon. Looking for your newest? Go to's Lululemon. What's new gear drops on Tuesdays. Every Tuesday, head to Lululemon.com to shop. What's new gear?
B
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Episode: How To Ask Better Questions with Elizabeth Weingarten | 347
Date: September 24, 2025
Host: Nicole Kalil
Guest: Elizabeth Weingarten (journalist, behavioral scientist, author of How to Fall in Love with Questions)
In this episode, Nicole Kalil dives deep into the value, power, and practice of asking better questions with guest Elizabeth Weingarten. The conversation challenges our cultural obsession with certitude, highlights the dangers of certainty “charlatans,” and provides practical strategies for cultivating a meaningful questions practice in our personal and professional lives. The episode is rich with personal stories, actionable tips, and memorable quotes, all wrapped in a tone that’s both insightful and candid.
“Questions are kind of this superpower, right? But a superpower that we don’t value as a society.”
— Elizabeth Weingarten (05:50)
Nicole and Elizabeth discuss how asking questions is culturally undervalued and often seen as vulnerability, especially for women in professional settings (09:24).
Research shows women tend to ask fewer questions than men in high-stakes environments, in part due to fear of being perceived as less competent or knowledgeable.
“Asking questions can be a form of vulnerability because you're acknowledging that you don't know something. And...in a culture where we are valued for what we know, admitting ‘I don't know’ can feel scary.”
— Elizabeth Weingarten (10:10)
Elizabeth outlines a questions practice designed to help people get unstuck and move forward in ambiguity.
The Four Elements:
Curiosity
Conversation
Community
“Community actually reduces our cortisol and lights up the parts of our brain that makes us feel like we're getting a reward.”
— Elizabeth Weingarten (30:28)
Commitment
Beware binary (yes/no) questions, which can close off possibilities. Expansive questions invite deeper exploration (27:13).
Be discerning about external sources: Are they thought starters or thought stoppers?
Always filter advice through your own inner wisdom and agency.
“Is it a thought starter or a thought stopper?”
— Elizabeth Weingarten (19:27)
Example: When facing marital uncertainty, shifting the question from “Should I get a divorce?” (binary) to “What would it look like for us to stay together?” (open-ended) led to more valuable insight.
It’s easy and tempting to seek fast fixes through experts, books, or influencers—but this risks giving away your agency.
“So many of us give up on our agency...we’re so eager to get out of discomfort that we seize on an answer rather than really doing the work to figure out, is this the right question?”
— Elizabeth Weingarten (21:00)
Instead, treat others’ answers as “breadcrumbs” or clues, not the final destination.
For yourself:
Back Pocket Questions (for yourself or others):
“What would I do if I wasn’t afraid?”
— Elizabeth Weingarten (34:45)
“How can I define my worth and value outside of my achievements or accomplishments?”
Nicole’s go-to: “What would I want for my daughter in this situation?” (37:05)
“If I put it in that lens, then it sort of forces me...if I want it for her, I should want it for myself.”
— Nicole Kalil (37:20)
“Can you tell me more about that?” for deeper listening and discovery.
The best questions feel expansive—they “open up the windows and doors in a room,” as Zen practitioner Joan Sutherland says.
This episode offers a powerful call to challenge certainty, ask better questions, and take ownership of the inquiries that shape your life, all while honoring your own intuition and building supportive relationships along the way.