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

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Coming up next on Passion Struck.

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, but to help me understand the experience better, to share wisdom from folks who had been there and come through it.

Welcome to Passion Struck.

Hi, I'm your host, John R.

Miles, and on the show, we decipher the secrets, tips, and guidance of the world's most inspiring people and turn their wisdom into practical advice for you and those around you.

Our mission is to help you unlock the power of intentionality so that you can become the best version of yourself.

If you're new to the show, I offer advice and answer listener questions on Fridays.

We have long-form interviews the rest of the week with guests ranging from astronauts to authors, CEOs, creators, innovators, scientists, military leaders, visionaries, and athletes.

Now, let's go out there and become Passion Struck.

Welcome to Passion Struck episode 605.

Whether this is your first time joining us or you've been with us on this journey for a while, thank you for being part of a global movement that's all about defying limits, living with intention, and making what truly matters matter most.

Before we dive in to today's episode, let's take a quick moment for reflection.

Earlier this week, I had the pleasure of sitting down with Gretchen Rubin in front of a live audience.

She's She's the best-selling author of The Happiness Project and also her new book, Secrets of Adulthood.

We explored how small truths, well-timed insights, and the courage to know yourself can shape a wiser, more intentional life.

If you missed that conversation, I highly encourage you to go back.

It's one of our most meaningful yet.

And I'm thrilled to share some exciting news with you.

Passion Struck was just named the number three life leadership podcast by million podcasts, standing proudly alongside shows like the Jocko Podcast and the School of Greatness.

We were also honored with the Gold Stevie Award for Best Independent Podcast at the 2025 American Business Awards.

A huge thank you to all of you who made that possible.

Now, let me ask you something.

What if not having all the answers was actually your greatest advantage?

What if uncertainty wasn't a problem to fix, but a doorway to deeper insight?

And what if learning to live the questions could transform how you navigate your biggest life decisions?

These are the powerful ideas we'll explore today with Elizabeth Weingarten.

Elizabeth is a journalist and applied behavioral scientist whose work has appeared in The Atlantic, Slate, and Behavioral Scientist.

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.

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.

And if you're just discovering the podcast, check out our episode Starter Packs at either Spotify or PassionStrike.com slash starter packs.

Curated playlists to help you dive deeper into themes like mindset, leadership, purpose, and emotional mastery.

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 a Clips channel at Passionstruck 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 is my conversation with the brilliant Elizabeth Weingarten.

Thank you for choosing Passionstruck and choosing me to be your host and guide on your journey to creating an intentional life.

Now, let that journey begin.

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

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?

For Elizabeth, it's always been Elizabeth.

I love 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.

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.

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 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.

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 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 kinds 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 when 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.

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 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 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.

This was in the early early days, and I was talking to this former SEAL, Mark Devine,

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 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.

I'm so glad to hear it.

And 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 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 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.

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 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 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 Cappas, this aspiring poet, is asking Rilke, who he's 27 at the time when he's writing to him.

Cappus 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 Cappas 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 Cappas 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 he never explained what he meant by living the questions now or even how to think about practically what it means to love the questions.

And he also, unfortunately, wasn't talking or thinking about how to do this in a time of AI, Google, smartphones, social media influencers.

So this book is really an exploration of how to fall in love with the questions of our lives, particularly the ones that can be painful, and especially in a culture in which so many of us have become addicted to fast, easy answers.

And I'll say too, this book is really about my journey to explore this question through science, history, philosophy, poetry, religion, art.

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 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.

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 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.

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 on every page, the best book ever written about behavior science and discrimination.

What was so meaningful about that book that it changed so much for you?

What a great question.

So this was indeed the book that made me interested in learning everything I could about behavioral science.

And the reason was it was really, 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 in journalism to explore underreported global gender equity issues.

And Iris was going to be coming to New America for a panel.

And so somebody shared her book with me so I could read about her and her work.

And it was one of those situations where I had been 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?

And so much of why we do the things we do 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.

I mean, 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.

And 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 the 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 MicroStrategy and trying to understand what made customers tick.

And 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 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 Yadin and David says, John, neuroscience is going to work for people, but it's going to take significantly longer to impact change.

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.

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 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.

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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 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, 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?

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.

And 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 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 and question asking, particularly in romantic contexts.

And I ended up writing about that for courts.

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 the pieces that I wrote for Behavioral Scientist was 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 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, 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 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 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.

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 of factors.

For years, I'd had doubts about my relationship with him.

We loved each other, but we both fundamentally 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 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 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.

And I just felt crushed under all of that.

And it was around that time that I came across Rilka 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 scientists, but this comfort with questions completely broke down in my personal life.

I Rilka talks about loving the questions.

Well, I had never felt further from loving the questions in my life.

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.

It made me think that given how many people go through divorces, perhaps more people should be asking

the difficult questions, but not just asking them, really thinking through them from the standpoint of what life would look like two, three, four, five, 10 years down the line, depending on how you answer the questions.

Because I would bet more people might stay together if they looked at this over a longer term horizon and they started to choice bracket their

decisions.

Well, it's a really interesting point because I think what I was feeling and I think what so many other people feel is it's so uncomfortable to be in that place of uncertainty, right?

And so I think

what I was craving in that moment was somebody just tell me what to do.

Somebody just give me an answer.

And I think in these moments of uncertainty, there's really a tendency that we have to want to rush to a fast, easy answer rather than explore and sit with the questions.

And I think you can look at it as, yes,

this can be a really uncomfortable experience, but.

in a way it's also it can be really freeing to realize and accept that well i don't have to have an answer right now i don't need to rush to take action on this particular unknown in my life.

I remember years and years ago, I was young and had

probably a four or five month old, and our neighbors had been married for over five decades.

And I remember talking to the wife, Karen, one day, and I said, what's your advice about being married?

And she said, well, they're good decades and they're bad decades.

And you've got to weather both of them.

And I know she wasn't literally saying it was decades, any relationship has ups and downs, but

absolutely.

Yes.

So

your book has some interesting names in it: peaches, pawpaws, heartwood, dead leaves.

What are they all about?

Yes.

So this is the questions framework that I introduce early on in the book.

And the idea is

to really help frame up

what are the questions that we're talking about here.

Again,

whenever I bring up the subject of questions, people are like, well, what questions do you mean?

And so I liken different types of questions to parts of a fruit tree.

And you can think about the first category of questions, as you talk about, as peaches, right?

These are the short-term answerable questions in your life.

Just as peaches ripen quickly on the tree, you can also get answers to these questions on a shorter timeline.

So these are are questions like, will I get the job?

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.

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.

When these are the dead leaves, right?

These are the questions that we eventually need to release.

I mean, 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, it may be time to let it go.

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

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?

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 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

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,

through

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.

So I found it also interesting that you both went to the same high school a few years apart.

Just a few years, yeah.

About 50 years, I think, apart.

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.

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 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 it really took about two years asking myself a lot of the difficult questions and really not liking the answers 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.

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?

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 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 and true for many people 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 to

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

guide folks through the flow of different potential questions 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've

the question, how do you maybe take action on learning about that question, figuring out what you may already know, 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 key to strengthening that sense of integrity.

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.

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 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?

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.

I mean, this is something that I've felt that fear too.

And so 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 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 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?

Thank you for sharing that.

Elizabeth, we were just talking about the question map.

And I thought maybe a good exercise would be to go through a story from the book that illustrates this map in action.

Elizabeth, one of the stories that I thought was top of mind for me was the story of Miguel.

And I think Miguel's journey is a common one in American history.

In his case, he ended up growing up in Mexico for the first few years of his life before he migrated to the United States and became an immigrant.

And he thought that if he studied hard enough, that earning an education would allow him to work through the barriers that he might face going from a lower income growing up to the life that he wanted.

But I think one of the things that is so important here, and it's one of the core areas that I focus on, in fact, I'm writing a whole book on it, is

he found himself when

he finally started to reach the points that he wanted with his education of not belonging, of feeling isolated, of feeling like he didn't matter.

How do questions, if you're experiencing that, allow you to find meaning, to find a sense of belonging, and to work your way out of something that I think so many people around the world today are facing?

I love that question.

And

one of the big things that I found in

my book and in my work is that

one of the most 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 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 within existing questions, but also that questions can connect us to entire communities.

And with Miguel and with so many others, he found a lot of comfort connecting with other undocumented immigrants who had

faced similar questions in their life, similar experiences of uncertainty.

And it really wasn't about getting answers from those communities.

It was about accompanying each other through that uncertainty and kind of witnessing the experience that we have

and that was something that i found that questions could be this portal to belonging and to feeling like you again don't necessarily need to know or find an answer to that question but questions that connected you with groups of people that were experiencing similar things.

And this was something, there was another story that I told in the book of Oliver, who was a guy who was questioning his gender identity and found similarly that 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 again are 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.

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?

So,

one of the most powerful ways that I've found to really explore: is this the right question for me?

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 that question was one that fundamentally wasn't giving me that open space to explore.

It was leading me down two paths, 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 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?

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

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?

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.

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.

Thank you so much, John.

It was such a lovely conversation.

I appreciate all of your thoughtful questions.

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 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, 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.

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.

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.

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