The One Question You’re Avoiding Could Change Your Life | Scott Simon & Gregory Stock – EP 824

Scott Simon, founder of the Scare Your Soul Courage Movement, and Dr. Gregory Stock, creator of the bestselling Book of Questions, reveal how asking the questions we avoid can unlock courage, connection, and meaningful change.

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

• 0:01John R. Miles?

  Hey friends, what if your biggest problem isn't that you're not doing enough, but that you've spent too long proving that you are enough? You can be successful, needed, and surrounded by people and still feel completely unseen. That's the problem I explore in my new book, The Mattering Effect. I show you how we become hyper-visible for what we produce while quietly becoming invisible to ourselves, and introduce the matter framework to help you reclaim meaning, autonomy, trust, time, energy, and reciprocity. Stop auditioning for your worth, start living from it. The Mattering Effect is available for preorder now at matteringeffect.com. What if courage isn't about doing something you're afraid to do? What if it begins with something much harder?

• 0:44John R. Miles?

  Asking yourself a question you may not want to answer? We often think of courage as taking action. But Scott Simon told me that the place people struggle most isn't physical courage or even ethical courage. It's the ability to ask and answer hard questions. Because a great question can take you beneath the surface to the parts of yourself you may have been avoiding, rationalizing, or simply never stop to examine. And sometimes the question itself can be the beginning of change. Take a listen.

• 1:21Speaker 01

  In my courage work, the number one area where people struggle the most isn't about physical courage or even ethical courage. It's the ability to ask and answer hard questions. And that comes from deeply inside of each one of us. And I think that's where a beautifully crafted question comes into play. A great question kind of allows us to get below the surface, to connect with deeper parts of ourselves.

• 1:52John R. Miles?

  Hey, it's your friend John, and welcome to Passion Struck. I'm so glad you're here. Whether you're a longtime listener or someone who just discovered the show, thank you for pressing play today. Maybe you've built the life you were supposed to want, but you've quietly wondered why it still doesn't feel like enough. If that's you, you're in the right place. Every week, I sit down with the world's top scientists, researchers, and thinkers to uncover what it actually takes to build an intentional life that matters. Thanks for joining me. Let's get into it.

• 2:33John R. Miles?

  Welcome back to Passion Struck, episode 824. In this series, we've been exploring what it means to become more adaptive, to change, grow, and navigate a world that constantly asks us to evolve. Over the past conversations, we've looked at adaptation from some very different angles. Angela Duckworth challenged us to think about how much our situations shape who we become. Marty Seligman took us deeper into agency, the belief that our actions can make a difference. David Epstein explored how we navigate uncertainty, develop our capabilities, and find focus in a world full of possibilities. And last week, Cole Brouwer showed us what adaptation looks like when you're 27,000

• 3:18John R. Miles?

  miles from home, alone at sea, and there's no one else who can take the helm. But there's a question underneath all of that. How do you know what needs to change if you're not willing to ask yourself the questions that reveal it? That's where today's conversation begins. I'm joined by Scott Simon and Dr. Gregory Stock, two people who have spent decades approaching the same human problem from very different directions. Scott is the founder of the Scare Your Soul Courage Movement, where he has helped people practice courage by stepping beyond their comfort zones. You may remember him from a few years ago in episode 300.

• 3:58John R. Miles?

  Gregory is the creator of the Book of Questions, the groundbreaking book that has spent decades getting people to stop, think, and have conversations that go deeper than the ones we normally have. Now, they've brought those two worlds together in their new book, The Book of Questions, Courage. And I love the premise because courage isn't always dramatic. Sometimes courage is having the conversation you've been avoiding. Sometimes it's admitting what you really want. Sometimes it's questioning a belief you've carried for years. And sometimes it's simply being honest with yourself. Scott told me that the area where most people struggle most isn't physical courage or even ethical courage.

• 4:44John R. Miles?

  It's asking and answering hard questions. Gregory explains why the right question can create a different kind of permission, a way to explore our values, our fears, our purpose, and the parts of ourselves we don't normally put into words. We talk about why questions can deepen relationships, why vulnerability can create connection, and why the conversations that make us slightly uncomfortable can sometimes be the ones we remember most. We also explore something especially relevant to the world we're living in right now. What happens to human connection when technology can give us an answer to almost anything but can't tell us what we want to become? And that led to one of my favorite parts of the conversation, the question of what

• 5:29John R. Miles?

  we should deliberately refuse to outsource to AI. Scott's answer was that questions involving our uniquely human emotions, relationships, history, and meaning require something more than information. They require human connection. And ultimately, this conversation comes back to a simple idea. A good question doesn't close a conversation, it opens one. It can reveal something about you. It can reveal something about someone you love. And sometimes it can change the direction of your life. So as you listen, I want you to think about this. What's one question you've been avoiding because you already suspect you know the answer?

• 6:12John R. Miles?

  Here's my conversation with Scott Simon and Gregory Stock. Thank you for choosing Passion Struck and choosing me to be your host and guide on your journey to creating a fulfilling life. Now, let that journey begin.

• 6:31John R. Miles?

  I am absolutely thrilled today to welcome Gregory Stock and Scott Simon to the Passion Struck podcast. Gregory and Scott, so great to see you guys today.

• 6:41Speaker 02

  Great to be here. Thank you.

• 6:42Speaker 01

  Great to be with you, John.

• 6:44John R. Miles?

  Scott, it is great to have you back on the program. The last time you were here, we were talking about your first book, Scare Your Soul, which I absolutely love that book. It has changed so many people's lives. But it's interesting, Scott, you write that you and Greg spent your lives walking toward the same place from opposite directions. And I kind of know that feeling. But Greg was going through questions and you were going through the same path through courage, as I just brought up. When did you first realize that your two bodies of work were actually talking about similar things?

• 7:23Speaker 01

  Oh my gosh. Well, first of all, I think my relationship with Greg is almost destined to be. And I'll tell you why. I have a little visual aid. For those of you who are not watching this and listening to it, I'm holding up a book called The Book of Questions. This is the original, and it's dog-eared. This was in my mom's purse when I was a teenager. And we used to read The Book of Questions at all of our family events. It really, in so many ways, bonded my own family. And I was a kid who was really shy and led kind of an invisible life. So, reading The Book of Questions and answering them gave me this sense of voice and of people listening and valuing my opinion.

• 8:03Speaker 01

  So it wasn't until 36 years later that I ended up meeting Greg on a Zoom, becoming friends, and really getting to understand his brilliance and his perspective. And that's, John, when I realized that he had spent so many years pursuing his passions through the art of question, designing and asking. And I had spent much of my life focusing on courage. And when we got together, I think we were mutually fascinated by each other's work. And after a while, it just kind of made sense. Let's combine the two things and write a book of questions all about courage.

• 8:43Speaker 02

  And I really enjoyed engaging with Scott. I visited with his family. It's really been wonderful. Questions about courage are so fundamental because courage is at the root of everything. And I don't mean charging towards machine guns, but making the call that you need to do, the little things that we do or postpone in life. And with my own daughter, who's now 22, just graduating from University of Southern California, I always taught her or pushed her to, when she feels fear, to turn in to do that very thing, assuming, of course, it's not dangerous.

• 9:23Speaker 02

  But most of the things that we're afraid to do and that we postpone and that sort of sit there in our lives and block up our progress towards whatever ends we're headed towards are not dangerous. They're just a little uncomfortable. And I think that Scott's story and his practice of that is very powerful. It's a little muscle of one step at a time. So I've really enjoyed this. It's been fantastic.

• 9:55John R. Miles?

  Gregory, I had a follow-up question for you. You launched the original book of questions back in 1984. And I was a freshman in high school at that point. And I remember the book coming out because so many people were talking about it. Ended up becoming a number one New York Times bestseller, ended up selling millions of copies. When you first started collecting these dilemmas, did you ever foresee technology would eventually make us more disconnected rather than less?

• 10:29Speaker 02

  No, is the answer. I didn't see that. And nobody really did. In terms of technology, at that point, the internet didn't even exist. And you were, this was all about using some tool, some challenge, some way of fostering deep interconnection and vulnerability and sharing, and moving very quickly away from the channels of conversation that are so boring and don't push into any depth and that we travel generally. And so I didn't even think of writing a book of questions. I just was coming up with questions because I'd had this wonderful experience at

• 11:13Speaker 02

  a retreat in the mountains where you're up talking about everything and about nothing for six hours into the wee hours of the morning. It was like 6:00 AM. And I thought, God, I haven't had that experience in the last 10 years. And there must be some way to make that happen. And that's where the questions came up as just something that might work. And I spent a year going around and just pestering people with questions. And it's so effective. In a very short period of time, you're talking about things that really matter. And it's particularly important when you head into areas of courage and personal change

• 11:57Speaker 02

  and growth. And so it's very reliable. And that's why it was successful at that level. I was told I was an idiot. This is stupid. Why would you write a book of questions? Why would you have to comment and explain to people? But there's a tension because there's no right or wrong answer. It's about who we are and what we care about. And we know best about that.

• 12:23John R. Miles?

  I interviewed a former Navy SEAL commander, Mark Divine, a number of years ago. I love Mark and I love his books. And I asked him a question about how he ended up becoming a SEAL. And he said, it goes, most people don't ask themselves the questions that need to be asked. And then they don't have the courage to pursue those questions. So when I was thinking about this book, those two lines went hand in hand to me. Because Scott, for you, after spending years of teaching courage, it seems like a logical step that oftentimes, not only do people fail to answer these questions, but even when they do ask

• 13:08John R. Miles?

  them, oftentimes, they don't have the courage to simply answer them honestly. Does that resonate with you?

• 13:17Speaker 01

  Oh, it does. I think in my courage work, the number one area where people struggle the most isn't about physical courage, or even ethical courage. It's the ability to ask and answer hard questions. And that comes deeply inside of each one of us. And I think that's where a beautifully crafted question comes into play. A great question kind of allows us to get below the surface, to connect with deeper parts of ourselves. And when we're doing it with somebody else, or with a group, because everybody is asking and answering together, you have this mass oxytocin release that allows you, as Greg said, to

• 14:01Speaker 01

  connect so deeply. And there is this beautiful feeling when we do something brave. I call it the after effect. It's really hard sometimes to walk into moments of bravery. So much of our own bodies stop us from wanting to do the things that are outside of our comfort zone. But there's this feeling after you do the brave thing that feels joyous and liberating and connected. And that's what I think happens when you ask and answer these questions with other people. You get connected and simultaneously, you have this beautiful sense of connection with each other. And that's a magical feeling.

• 14:40Speaker 02

  That's absolutely true. And I do think it would be useful because questions can conjure up anything. There are lots of different questions. There are leading questions. There are informational questions. These are a particular type. I call them a questic, because it puts the quest back in questions. It's a personal growth. It's an effort to explore and see what we're doing. An example would be Scott and I made a presentation at South by Southwest in the spring. And we were riding in an Uber. And one of the questions, so talk to the Uber driver, one of the questions is, you're walking alone in the woods, and you come across a

• 15:22Speaker 02

  little spot, and there's a clearing, and you see a little paper bag. And you reach over and you open it up, and there's $50,000 in it in cash. And it says, this was saved for my daughter so that she could travel the world. And she just found that she had stage four cancer, and she just died last week. I'm leaving it for you. Use it to live your life now. What would you do? Where would you go? What would you do? So we asked that to the Uber driver, and immediately, we're launching into a discussion of why she would take her kids to Japan. And so you're creating these hypothetical situations often that

• 16:06Speaker 02

  lets us strip away all the reasons that we have for not exploring our passions and who we are. And I think that's something that you think about a lot, just from the title of this podcast, Passion Struck. It's giving us permission to explore those realms that then can have very profound impacts on us.

• 16:27John R. Miles?

  Absolutely. And one of the things that this podcast is really about is, I think about Passion Struck is really the topic of, how do you become you? How do you become the ideal version of yourself that we all aspire to be? How do you live truly alive? How do you flourish? And I think questions play a huge role into that. And one of the things that I really grabbed from the manuscript when I was reading it, is that questions don't merely reveal who we are. It creates something that really didn't exist before.

• 17:10John R. Miles?

  Is that a good way of thinking about this?

• 17:13Speaker 02

  I think that questions are a window into our soul, into who we are. And it's really interesting in that the questions that I like the most, some people just shrug because that's not where they are at that moment in time. Another one that might be about betrayal, or about exploration, or whatever it would be, resonates because we're grappling with that. They have a right time and a place and a moment. And then they really allow

• 17:48Speaker 02

  to come to understand who we are. Because if we're going to be that person, if we're going to move in a direction that is expansive rather than contractive, then we need to understand that. And it's a very safe way to do it in hypothetical situations that put our values and our sense of purpose and meaning in conflicts. Because otherwise, it's too easy. And doing it, at least for me, doing it with other people, is such a way of deepening relationships. And there's been a lot of scientific research around that. They actually took questions from the original book of questions and used them in paired groupings and found

• 18:29Speaker 02

  that people talking about these sorts of supposedly difficult issues, but actually, they're not more awkward than anything else. You feel closeness for the other person that's dramatic and very reproducible. So that's why this was so popular and why questions have spread as a mini genre, because they really lead to connection and exploration and discovery and personal value. So absolutely, John.

• 19:00John R. Miles?

  We'll be right back with more of my conversation with Scott and Gregory. As you're listening, I want you to think about something. What is one question you've been avoiding because you're not sure you want to hear the answer? Scott and Gregory make a compelling case that some of the most important breakthroughs in our lives don't begin with an answer. They begin with a question we're finally willing to ask. And if this conversation is giving you a new way to think about courage, connection, or the questions you're asking in your own life, I'd love for you to stay connected. Subscribe to Passion Struck wherever you listen to podcasts. And if you're watching on YouTube, make sure you subscribe to the channel so you don't miss our next conversation. And I'd love

• 19:42John R. Miles?

  to hear from you. What question has changed your life? Share it with me on my Substack at The Ignited Life, Instagram, or wherever you connect with me. If you know someone who could benefit from this conversation, send this episode their way. Now, a quick break for our sponsors. Thank you for supporting those who support the show.

• 20:07John R. Miles?

  You're listening to Passion Struck right here on the Passion Struck Network. Now, let's get back to my conversation with Scott and Gregory.

• 20:15John R. Miles?

  And Scott, I've got a part B to that question. Many of the questions in the book force readers to confront things like their hidden beliefs, perfectionism, or things they swallow, in many cases, to keep the peace in their home environments, could be a work environment. Which question in the manuscript personally unsettled you the most?

• 20:37John R. Miles?

  When you had to answer it yourself?

• 20:39Speaker 01

  Oh, John, I knew you were going to ask that question. There is one, I think, that is maybe my favorite. I don't think that it's Greg's. And I just want to take a second, John, to tell you and your audience. Going into this, I thought Greg and I were going to have this great lovely experience of banding back questions and loving every second and have immediate agreement. And it was, in a fascinating way, very different from that. We would begin to draft a question and immediately we would start to have different perspectives. Greg would say, well, Scott, how would you answer that? And I would answer, and then Greg would answer, and then all of a sudden, the question would morph and change.

• 21:21Speaker 01

  And I think at the end of the day, we ended up with a question that distilled down the essence of what we were talking about. And that, to me, is almost what I'm the most proud of in this entire book, is that every question has been battle-tested by Greg and me. And we got, I think, down to the essence of what is most important. So the question that absolutely unties everything inside of me is the following, and I think it's question number two in the book, and that is, what is one lie you are telling yourself to keep yourself safe, but is really holding you back?

• 22:03Speaker 01

  And that question cuts to the core of the kind of narratives that we tell ourselves, maybe that were told to us at some point in our lives, that we have continued to carry forward, that protect us in some ways, but at the end of the day, are holding us back. And so that question, while being, I don't know, maybe 20 words, is maybe my favorite.

• 22:28Speaker 02

  And what's your answer?

• 22:29Speaker 01

  And the hardest to answer.

• 22:31Speaker 02

  What's your answer? Why don't you share that again?

• 22:34Speaker 01

  Well, I have so many answers to that question, which is, I think, another mark of a great question. But I think the way that I answered it to Greg when we were designing it is, one lie that I tell myself constantly is that I have to rely on other people's expertise to do my best work, that I need to hire other people or ask other people constantly about what I am doing to be able to achieve what I want to achieve. And I've had so many experiences where I've hired other people to help me do something, and at the end of the day, it's always me.

• 23:15Speaker 01

  It's always me that's doing the elemental, essential work and not the person that I have brought in. And so, in essence, it's about trusting my own intuition, which doesn't come naturally to me, and to have the confidence that I know best, that when it comes to the things that I'm the most passionate about, to trust myself. So that's my very honest answer to that question. And I've asked this question now many times around the country as I travel, and I'm just constantly blown away by the honest and vulnerable responses that I'm getting. It's, I think it's a really beautiful question.

• 23:53Speaker 02

  And John, it's one thing you were asking about questions, and I think there are two fundamental kind of components of human interaction, social interaction. And one is storytelling, and we all know the power of storytelling in advertising and film and books everywhere. And the other is questions, and they do a little dance. Questions invite stories that reveal things, that invite more questions, that invite more stories. And it really is this wonderful sort of interaction process that you can't predict where it'll go, but it goes to very interesting places and leads people towards revealing things

• 24:37Speaker 02

  that maybe they hadn't been hiding, but they hadn't had an opportunity to express, stories of their childhood, stories of challenges that they've faced. And it's really just wonderful. And these questions about courage can really be life-changing, because your life can change, as you know very well, in an instant. You get an insight, and suddenly, the world looks different. Your life looks different. And so, I just love this, and I've been doing it for decades and decades, and I never tire of it.

• 25:11John R. Miles?

  Well, gentlemen, one of my favorite questions was number 14, and thank you both for your points on that. And 14 is, if you could snap your fingers to permanently eliminate one of your fears, which would it be? And what ways might your life expand with that fear gone? Scott knows me well. Gregory, you're just meeting me, but when I was a youngster, living where Scott lives now, I was living in Bay Village, which is not too far away from Cleveland. I had a pretty bad head injury, and it caused me to have a sensory processing disorder and a severe speech impediment, two things that I still deal with.

• 25:51John R. Miles?

  And so, one of my fears when it comes to speaking, even in this setting, is that my head, what's going on in my brain often operates at a different speed than what comes out of my mouth. So sometimes, I never know what might come out or how it might sound. And it was interesting, because I was doing pickups for my audiobook yesterday, and there were a few situations where I completely read different words that were on the page, and that's a great example of it. So if that fear were gone, I would feel a much more comforting state when I'm on stage and in front of people.

• 26:35John R. Miles?

  And I think because of that fear, sometimes it has caused me, in many social situations, to be much quieter in how I approach them than I would if that fear were gone, just to take my example of one.

• 26:50Speaker 02

  That's really interesting, John, and I will throw out something, in that sometimes the fear is that something uncomfortable is going to happen. I used to feel that way about public speaking a lot. It no longer bothers me, not because I won't mess up, but because things happen. And you can see that with a comedian on stage where they have this moment that they just, it bombs, and some people try and ignore it or try and pretend it didn't happen, and it feels awful. Nobody likes it. And others just go into it. They embrace it. That's what happens. And we love that, because people don't respond positively because we're strong.

• 27:34Speaker 02

  They respond positively because we're real and we're open and we're vulnerable. And so, you, it seems to me, are just citing, because of your mention of that and the way you've dealt with it, is things like that may happen, but you're more comfortable with it. You are open about it. People are sympathetic. They're not going to ding you badly because of that. It makes them feel more powerful and more comfortable. So my suspicion is you've really dealt with it largely at this point.

• 28:07John R. Miles?

  Thank you for sharing that, Gregory, and I end up leaning into it. I remember I interviewed Bo East, and I'm not sure if you guys know who Bo is, former NFL player, but he's now a very large public speaker. And one of the things he always talks about is, people never want to hear your most triumphant moment when you're on stage. They want to hear your most vulnerable moment. And so oftentimes, if I'm struggling with it, or if it does happen, I just turn it into a vulnerability moment, where I then lean, turn it into a story, and I lean into it instead of ignoring it. And that's worked really well for me.

• 28:46Speaker 01

  And John, I think that's

• 28:48Speaker 02

  Big difference. Let me just say, because when you do that, everybody is thinking of their moments of vulnerability and how worried they are about this or that. And so you're giving them permission to fail, to be vulnerable, to mess up. And so they come away strengthened and are grateful for it. And that's probably why you have a successful podcast show where people respond to you and your audience cares about you is because of that authenticity.

• 29:22John R. Miles?

  Scott, did you want to say something?

• 29:23Speaker 01

  It's funny, Greg and I have clearly worked together for a very long time because that's exactly what I was going to say. That when we lean into those moments of vulnerability and we share those things, it allows people the permission to do the same. And I really felt when Greg and I were writing this book, AI is starting to create such an impact in our world. Our phones have become distraction machines. There are so many ways and opportunities we have in life to not go deep and to not connect and to isolate ourselves. And to have a vehicle that allows you in a way to be vulnerable because you just flipped to a page is really powerful.

• 30:05Speaker 01

  And it's really an invitation to connect in ways that you may not. If you just say hello to somebody, you meet them. Let's say you're at a cocktail party or you're getting to know someone over a cup of coffee. Your immediate sense is to not go deep, to not go vulnerable. You may ride the surface. A book of questions allows you that kind of common invitation to go deep and to go deep fast. And so to do so allows us really to connect in ways that are so far beyond the kind of answer-rich society that we're living in, where we're so focused on what's the answer to somebody or an answer to something,

• 30:47Speaker 01

  when really, at the end of the day, the kind of the magic exists in the question that comes before.

• 30:53Speaker 02

  And an important extension of that is that the questions are crafted so that there is no right or wrong answer. They're not leading questions. There's no analysis that if you answer question seven, 22, 57, and 80 in a certain way, then you're fundamentally a caring, good person. And so there's none of that. It's just a question that you have a personal response to, a reaction to, and that you can choose to be clear about it, to be real about it, or not to delve into it. But there's no, it's not a test, okay? And that creates attention and it creates a freedom.

• 31:38Speaker 02

  Because, and I really believe that's important. In fact, we're doing, using questions, some of these questions and some like it, with family caregivers, people who are caring for someone informally. They're not being paid for it. There are about 10 million of them that care for somebody with Alzheimer's and dementia. And we have a way online of connecting small groups of people and then feeding one question a day that they discuss asynchronously. So it's a chat. And the reaction is extraordinarily powerful because this is very isolating. It's, you need social emotional support. And the response is, I don't feel so alone.

• 32:21Speaker 02

  It's so wonderful to know that others are grappling with this same thing. It makes me feel less isolated. It makes me feel like I can manage in some way. And that's the way it is with all these things. It's, we really have so much to share with one another.

• 32:39John R. Miles?

  I think that's a very important example. And we personally have a very close family member who's experiencing dementia. And I know for my wife, it takes on a tremendous toll for her because it is an isolating experience when you're the one who's primarily dealing with it and you don't really have a support structure of other people who know or understand what you're going through and how difficult it is, especially when the person who you probably would have gone to for that comfort is the person who you're now having to take care of that you can no longer go to. So I think that's a really good use of this that you guys have brought forward.

• 33:24Speaker 01

  And it also speaks to this issue of loneliness in our society in general, right? The ability that we're not communicating, that we're isolating. And can we find ways to lean back into the kind of sit out on the stoop and have conversation kind of life that we had in our society, where you really know people around you. You really, you have a sense of what they're all about and what's happening in their lives. That's such an important part of happiness and of leading a flourishing life and of community, of curiosity. I have younger nieces and nephews and I sometimes bring these questions to our family dinners that we have together, the ones that Greg and I developed.

• 34:08Speaker 01

  And one of them that I asked at a dinner table not that long ago was, who's a hero of yours and why? Which gets to the courage question. And everybody put down their phones and everybody started to talk. And my father, who's 83 and was at the table, said that my mom, who was sitting next to him and has Parkinson's disease, was his hero. And the emotion and the connection, and then the kids answered in the way that kids answer. And so I think this whole sense of we're living in a society now where it's so easy to isolate from one another that a simple, good question can connect you in ways that are so memorable

• 34:52Speaker 01

  and are so loving and touching.

• 34:55Speaker 02

  Vessel for the exchange is really important because you have social media, which is so socially isolating. And the reason for that is that it's one to many. We're inauthentic, we're self-promotional. It's not about building connection. That happens in small numbers of people, one-on-one, one on a few. And then you have these wonderful exchanges that occur, that go deep, that are very personal. So it's about slowing down, giving moment for that depth. And I would guess that Scott, you probably devoted a long time for that one question and all of the things that spun out from it.

• 35:41Speaker 02

  So that's the kind of inspiration that you create.

• 35:44Speaker 01

  Greg, I think that's absolutely right. It's almost like one question spawns all these little questionlets that continue on in conversation. And that's absolutely right. That one question kept the family talking for an hour and talking about real things that matter and that people are passionate about. And yes, some of the answers were super funny and people cracked up. And some, like I mentioned, my father, were so touching. And then all of a sudden, everybody leaves and they feel like, oh, my gosh, that was the best dinner we've had in ages. And you only asked one question and that's what kicked off this whole experience. And I think what's so wonderful about doing this project with someone like Greg

• 36:29Speaker 01

  is he literally created this category. All of these card decks and wonderful other ways that people are connecting, other books of questions and things like that, they all respond from the original book of questions. And so to be able to take that book, which came out in the mid 80s, and to bring it into 2026, to update the kind of discourse, the kind of questions. There are questions around AI, there are questions around society, around relationships, around health and money. And the key kind of commonality between all of the questions is that each one, in some different way, gets to the issue of courage, which was so important to Greg and me.

• 37:14Speaker 01

  So bringing this book from the 80s now, all of a sudden, into 2026, into our current age, and in a way that leans into what really matters most in terms of leading a courageous life.

• 37:29Speaker 02

  And John, this has been prepared. It starts with a book, but there's QR code within the book. So you can actually go and answer in an online environment and then see how others respond to it. And it's very touching. And I don't mean just yes or no, a little comment, a deeper answer, an open-ended answer. And my goal with these at this point is to put this in an environment where we harness the capabilities of AI and communications technology, not to try and replace human-human connection, but to enhance it, to further it, to allow it to occur in multiple languages with instantaneous translation. So we're putting all that together.

• 38:13Speaker 02

  And the book itself is the starting point for all sorts of potential interactions that reinforce that that underlying sort of desire for depth and connection and intimacy. A good question doesn't lead to answers and closures. It leads to more questions and openness and further exploration. So that's the passion behind it and the discipline behind this collection.

• 38:43John R. Miles?

  Hey Scott, I wanted to ask, are you familiar with the work of Nick Appling? He's a professor at the University of Chicago.

• 38:49Speaker 01

  Yes.

• 38:50John R. Miles?

  I had him on the podcast.

• 38:51Speaker 02

  He took, he did the work that he did that you're going to mention to. He took questions from the original book of questions. That's what it was based on. Go ahead.

• 39:00Speaker 01

  He sure did.

• 39:01John R. Miles?

  No, it's so funny. I interviewed him for his book, A Little More Social, which came out this spring. But one of the things that people often talk about him about is his commuter train studies. And what I loved about this is the study basically took

• 39:19John R. Miles?

  Three examples. One, you sit in isolation. Two, you subtly have a conversation. Or three, you openly ask the other person questions and have a more robust conversation. And they went into it thinking that the people who were going to have the most pleasant train ride were the people who sat in silence. And they found it was the exact opposite that was true. And so it reminded me of the loneliness topic that you led with Scott. But it also led me to believe, when you get into this courage aspect, do you think it's the lack of courage in a situation like that, when you're on a train,

• 40:00John R. Miles?

  that prohibits people from wanting to open up the discussion and start asking the person next to them questions? Or is it something else?

• 40:10Speaker 01

  I think it is a lack of courage. Courage, to me, is the foundation stone for all of the things in our lives that bring meaning, but it oftentimes doesn't come naturally. And John, you and I have talked about this many times, that both our bodies and our brains are designed to keep us safe. They're designed to keep us status quo. It wants to steer us away from possible negative interactions, things that happen that are maybe uncertain. We don't know what's going to happen. And so when we're on a train and there's some stranger sitting next to us, it is not in our nature to break out of that kind of mode of comfort and engage, because we just

• 40:55Speaker 01

  don't know what's going to happen. John, you probably remember from our prior conversations, I think I've bought about 250 cups of coffee for strangers and had conversations with them as we're waiting for our coffee. It's hard every time, even though I've done it 250 times. It's always hard because there's this sense of uncertainty. You just don't know what the person is going to say. But I can tell you, probably out of 250 times, maybe there were four or five where the interaction just didn't go well, or the person said no, or felt really awkward and uncomfortable. The rest were lovely. They were amazing. And the whole conversation piece that we would have after we ordered the coffee and

• 41:40Speaker 01

  we're waiting for it is all about questions. Who are you? What's exciting you in your life right now? Tell me a little bit about you in a way that maybe some people don't know. And those conversations are fantastic. So I think we have to be aware that our initial inclination is to not engage. It's to just do our thing, open our magazine, or put in our earbuds. And it's literally when we take out our earbuds and we ask somebody an interesting question, that's when connection and curiosity start to bloom.

• 42:20Speaker 02

  And there's an element of that, too. I would say it's less about courage, although it is in a way. It's about permission, because we don't want to be intrude on another person. But that's what a collection of questions of this sort provides, because it's, oh, here's an interesting question. Let me share this with you. Or I'm asking people. It gives you permission to make that initial step. And that, so it lowers the requirement. When Scott does something and buys somebody coffee, or that is an unusual ask. Whereas to just, you're looking at a book, it's a funny, it's like with a dog.

• 43:02Speaker 02

  If you have a dog, it's really easy, because there's that thing, it's the gift of improvisation. It's the focal point for interaction. So sometimes, these kinds of things, when I did the original book's question, people would carry them around. They'd have them sitting on a coffee table. And that kind of still works at some level.

• 43:21Speaker 01

  I just want to say very quickly on that point, I agree with Greg. We made a very specific decision on this book. These days, you can make a book any size you want and any, in any format you want. And we felt very strongly that this book was this little four by six book that is portable. It's not a big, heavy, hardcover book that you can't fit into a purse or a pocket. We want this to be in public settings. We want this to be in people's workbags and purses, for that very reason that Greg just said, that there will be, hopefully, lots of opportunities for people to literally pull it out and begin to have a conversation. Just turn to any page.

• 44:03Speaker 01

  All of the questions and challenges in the book are random, they're randomized, so that it doesn't matter where you start. You literally just open up to a page and you can begin your conversation.

• 44:18John R. Miles?

  Scott, I had a question I wanted to direct to you. And then I have a second part that I want to direct to Greg on it. We're at a point now where AI can generate an answer to almost any question that we ask it instantly. But sometimes I question the answers we get back from it. And oftentimes, I find that AI ends up flattering you in many of the responses it gives you, instead of giving you an honest response. So it leads me to wonder, what kinds of questions should we deliberately refuse to outsource to AI?

• 44:56Speaker 01

  Wow. Certainly, any question that has to do with real, human emotion. I think AI has tremendous positives and possibilities. In fact, Greg is, speaks on AI all the time around the world, and I don't know anybody who speaks more brilliantly about it than Greg. But there is something so innately human about the interaction that we have with another person. And I have yet to find an AI model that really understands the depth of human emotion. And when I said before that Greg and I would start working on a question, and we would pull it apart, and we would ask it in different ways, and we would reformulate it, and we

• 45:39Speaker 01

  would bring our own lives and vulnerabilities and passions to it. I don't think a model can do that. There is no LLM that understands my past, my worries, my joys and triumphs, how it affects how I see the world. And it also can't have an ongoing interaction with somebody where you learn a little something more about them and you can go deeper. It doesn't have the ability to connect on a human level. And I think that's what we're missing. We say in the introduction to the book that AI and Google can provide us answers to anything, but it can't tell us who we want to become.

• 46:24Speaker 01

  It can't tell us the kind of question to ask a parent about their lives before it's too late. It's not the type of entity that can guide us in a way that is as deeply human as doing it with somebody who cares about us. So I think anything that has to do with our unique and innate humanness is in the purview of, of the great question. And I think AI has its uses elsewhere, but John, that's how I would answer that question.

• 46:57Speaker 02

  I love AI, I talk about it all the time. And I think we will actually form deep relationships with AI, but not yet. And AI, and I've tried really hard, because AI is really good at generating prompts. If you say, ask, give me a bunch of questions about whatever it is, two seconds later, you'll have any number of them. But they're not really profound, good questions. And Scott pointed out the reason that is. It's because it understands the syntax and the structure, so they look good initially, but they don't really, it doesn't understand pain. It doesn't understand humiliation. It doesn't understand yearning and love, has the words.

• 47:42Speaker 02

  And I would say that in terms of your interaction with AI, when it gets answers, we actually can get interesting answers and prompts and explorations if we treat it correctly, which is this brilliant entity that has all sorts of knowledge and also is a complete idiot. So if you go, what? That's ridiculous. I don't feel that way. I'm blah, blah, blah, blah, blah. Then, and go back and forth, it often leads you to interesting insights and to processes that are quite engaging and lead you forward. My daughter, who's at USC, does that all the time, where she'll finish a phone call and she'll go, oh, I just messed it up and I did this and that.

• 48:26Speaker 02

  And then goes, no, you, this happens all the time. They're probably not explaining about that. And they'll go back and forth. So it's a way of having attention and engagement around these things. But they're not at a point this prime where they can really either craft a good question or really probe meaning in an easy way. They just aren't. But who knows, as we move forward into the future? I think a lot about the possibilities of AI.

• 48:56Speaker 01

  John, I just want to tack back to a story that we said earlier, and that is, when Greg and I were in Austin for South by Southwest, we were drafting questions. We were staying up late into the night, working on questions together. And then we would get in an Uber and ask the question that we had just drafted to the Uber driver. And I remember one time, we had asked the question, Greg mentioned it before, about the finding $50,000 in cash on a boulder and having to determine what you would do with it, to honor this life. And we, I remember the Uber driver, when we were done, parked the car, and we stayed in the car, answering the question with each other. That is not going to happen with an AI model.

• 49:38Speaker 01

  That is only what happens when human beings get together and start sharing, and one question leads to another. And when you ask a great question, sometimes it isn't your own response that matters the most. It's the response of someone else that gets you thinking in a different way. And you go, oh, my gosh, I never thought about it that way. You know what? I'm going to change my answer. I think about it this way now. And it becomes this evolving discussion. And I'll never forget sitting in that Uber, well after we had arrived at our location, just continuing to talk. And I think what's really special about this kind of interaction, and I don't, I agree with Greg, AI may get there at some point, but it's not there yet.

• 50:24Speaker 02

  And there's something further on that is that it really is interesting how rarely we go to these places of deep meaning and value and passion and what we care about. And you'll often get in a situation where somebody and their spouse will be answering, and one will look at the other and say, really? I can't believe you would say that. That it's like, I've lived with you for 20 years, and I had no idea, right? Because we have these little channels of conversation that are often relatively superficial compared to the deeper places that we can go in five minutes if we give

• 51:09Speaker 02

  ourselves permission.

• 51:11John R. Miles?

  Gentlemen, I have one question left for each one of you. I'll start with you, Scott. If everyone listening could ask one question tonight that might make their life or relationship meaningfully different, what question would you give them?

• 51:26Speaker 01

  I thought you might ask that question, John. So I went back through our manuscript, and I chose one. And it actually is the last question in the book. And it, I think, gets to the essential nature of courage, and it's this. What is something extraordinary you've done and done well before you felt either ready or confident?

• 51:51John R. Miles?

  And why that question?

• 51:53Speaker 01

  I think that we don't honor our own courage in so many ways. We wait to be ready. We wait for that moment where we're going to feel confident, and we have all of the tools and all the skills to do it. At the end of the day, we have all done extraordinary things. And we've done them before we were ready. And I think when you ask and answer this question with somebody else, this thing starts to bubble up, and that is, yeah, some of the greatest things I've done in my life have been done before I was ready. And that gives you greater motivation and license to go ahead and do those things now. Do the

• 52:33Speaker 01

  things now that you know are important. Take courage, and don't wait to be ready. Just take action now.

• 52:42Speaker 02

  I like that. And I'll throw out something that's a little variant of that. I don't have a single question that I would go to, but it would be, one of the questions is, what's something, the most courageous thing you've done this week, basically? What's something courageous that you've done? I don't know the exact wording of it. And how did you celebrate it?

• 53:08Speaker 02

  And that's really important, because we don't give ourselves credit. We do little things all the time that we rarely interpret as courage. And they are. And when we do celebrate them, and we acknowledge it, and we congratulate ourselves, it builds that strength. And so I think these little steps are extraordinarily important.

• 53:32John R. Miles?

  And I'll just share mine. One of my favorite ones was question 78. What is the best thing that has come into your life because you pushed beyond safety and comfort? And it reminds me of this concept of the reverse bucket list that I learned from this gentleman who's got the domain, the bucket list guy. And the reverse bucket list is when you go through all the things in your life that you never thought you'd be able to accomplish, and that you had the perseverance to achieve. It gives you the confidence to do so many of the challenges that are holding you back that lay ahead of you. So that was one of my favorite ones. Well, gentlemen, I loved having you both on the program. I

• 54:15John R. Miles?

  am so excited for this book to launch, and I love how you have put the challenges as part of this to express the courage, but also the QR codes, as you mentioned, Gregory, that people can go to make this book a living thing. Where is the best place people can learn about this, pick up the book, pick up the additional things that are available to them beyond the book?

• 54:38Speaker 01

  So the best place to go is couragequestions.com. That'll have all the links to purchase. It'll have all of the external links that Greg mentioned to carry the courage journey further. And yeah, we're happy to have anybody come visit that site and learn more about the book. And it's, it'll be-

• 54:57Speaker 02

  And what's the launch date now? What's the launch date now?

• 55:01Speaker 01

  The launch date is September 22 of 2026.

• 55:05Speaker 02

  Good. Well, it's been a real pleasure, John. I've enjoyed the conversation. I really enjoy your energy and spirit, and it's wonderful to engage with the three of us. So, thank you very much. I appreciate it.

• 55:21John R. Miles?

  It's been an honor having you both on the show. Thank you so much for joining us. And I look forward, as I said, to the book coming out, because I think it's got the ability to influence tons of people who need these self reflecting questions more than ever right now.

• 55:36Speaker 02

  Okay.

• 55:36Speaker 01

  Thanks, John.

• 55:38John R. Miles?

  I hope that conversation with Scott Simon and Gregory Stock gave you a new way to think about courage, connection, and the questions we ask ourselves. One of the ideas I keep coming back to is that a question can create a space for something that didn't exist before. It can open a conversation. It can reveal something about ourselves. And sometimes it can give us the courage to take a different path. But that raises another important question. Where does that sense of agency begin? Where do we first learn that we can make choices, solve problems, explore the world, and decide what matters to us? That's where we're headed next week. On the next episode, I'm joined by Dr. Peter

• 56:17John R. Miles?

  Gray, evolutionary psychologist and author of Restoring Childhood. Peter has spent decades studying childhood play, education, independence, and human development. And he makes a powerful case that play isn't simply something children do for fun. It's one of the ways they learn to take charge of their own lives. Maybe so important to developing agency. What happens when adults begin managing too much of a child's life? And how children discover what they're passionate about? And there's one idea from our conversation that connects directly to the journey we've been on throughout the Adaptive Human series. How do you discover

• 56:59John R. Miles?

  what matters to you? Peter's answer is surprisingly simple. You discover it as a child in play. Take a quick listen.

• 57:08Speaker 03

  How do you discover your passion? How do you discover what's meaningful to you? What matters to you? You discover it as a child in play. You play at this, you play at that. You play out of various things. You acquire kind of a broad understanding of things by playing and exploring in various ways. But then something really hits you. I love to do this, right? I really love to do this. And you do it enough that you become good at it.

• 57:40John R. Miles?

  That's our next conversation on Passion Struck. Until then, remember, the better we understand the forces shaping us, the more intentionally we can choose how we respond to them. I'm John Miles, and as always, stay curious, stay intentional, and stay passion-struck.