Passion Struck Podcast · With John R. Miles

How to Build Courage: The Questions That Help You Live More Bravely | Gregory Stock & Scott Simon

September 24, 2026

How to build courage is a question that can easily become abstract. We tend to associate courage with moments that are visibly difficult, dramatic decisions, public acts of bravery, or situations in which the stakes are immediately obvious. Gregory Stock and Scott Simon approach it from a more intimate direction. They suggest that courage often enters our lives through the things we quietly postpone: the conversation we have been avoiding, the decision we keep reconsidering, the fear we rationalize, or the question we know we should ask ourselves but would rather leave unanswered.

Their collaboration brings together two bodies of work that might initially seem separate. Gregory Stock has spent decades designing questions that help people examine what they value and how they understand themselves. Scott Simon has built his work around practicing courage through deliberate encounters with discomfort. When those ideas meet, a stronger possibility emerges. A question can expose something we have been protecting ourselves from seeing, while answering it honestly can require the very courage we are trying to develop.

The result is a different way of thinking about courage. It is less about becoming fearless and more about becoming willing to look honestly at what matters, understand what fear is doing in our lives, and decide what we are prepared to do next.

How Questions and Courage Work Together

Courage often begins before the visible act of bravery. It begins in the moment when we recognize that something matters enough to require a response from us. That response might be a conversation, a decision, an admission, or a willingness to move toward something that makes us uncomfortable.

Gregory Stock describes courage in precisely these everyday terms. When he talks about turning toward fear, he is not advocating reckless behavior or ignoring genuine danger. He is talking about the many ordinary situations in which discomfort becomes a reason to postpone action. We delay the call, avoid the conversation, hesitate to make the decision, and gradually allow the unresolved issue to occupy space in our lives. Gregory sees these moments as opportunities to practice courage through small, deliberate steps.

Scott Simon brings a complementary perspective from his work with courage. He explains that the area where people often struggle most is not physical courage or even ethical courage, but the ability to ask and answer hard questions. A well-crafted question can move beneath the surface and bring us into contact with parts of ourselves that ordinary conversation rarely reaches.

That connection is central to their collaboration. Before courage becomes action, there is often a moment of recognition. A question can create that moment by asking us to pause long enough to see something we have been avoiding.

What Difficult Questions Reveal About Us

Gregory describes questions and storytelling as two fundamental elements of human interaction. A question invites a story, the story reveals something, that revelation generates another question, and the conversation continues. The process is unpredictable, which is precisely what makes it valuable. People begin revealing experiences, childhood memories, challenges, beliefs, and aspirations that they may never have had an opportunity to articulate before.

This is also why the questions Gregory and Scott create are not designed to produce predetermined answers. Gregory emphasizes that there is no right or wrong response. The point is to explore who we are and what we care about rather than determine whether someone has answered correctly.

Scott describes one question in particular as having an unusual ability to reach the core of the stories people tell themselves: what is one lie you are telling yourself to keep yourself safe, but is really holding you back?

When Scott answers that question personally, he recognizes a belief that he needs other people’s expertise to do his best work. His reflection leads him toward a more difficult realization: ultimately, he has to trust his own intuition and recognize that he is responsible for the essential work. The value of the question comes from its ability to expose a protective story that has outlived its usefulness.

That is one of the deeper functions of self-reflection. A useful question does not necessarily give us an immediate solution. It can show us the structure of the problem more clearly.

How Vulnerability Turns Questions Into Connection

A question can remain intellectual, or it can become personal. The difference often depends on whether we are willing to answer it honestly.

Scott describes what happens when people cross that threshold together. There can be discomfort in entering a vulnerable conversation, particularly because we cannot control how another person will respond. Yet once people take that step, the experience can produce a sense of liberation and connection.

The family dinner story Scott shares illustrates this beautifully. He describes asking his family, “Who’s a hero of yours and why?” Everyone put down their phones and began answering. His 83-year-old father identified Scott’s mother, who was sitting beside him and living with Parkinson’s disease, as his hero. What began as a simple question became an unexpectedly emotional moment of recognition and connection.

The significance of the story lies partly in its ordinariness. No elaborate exercise was required. Someone simply asked a question that gave the people around the table permission to say something meaningful.

Gregory’s description of questions and stories helps explain why this happens. One question can generate several more, and each answer can reveal another layer of the person responding. The conversation becomes less about exchanging information and more about discovering one another.

In that sense, vulnerability is not merely a personal experience. It can become a social experience. When one person risks being honest, they often make it easier for someone else to do the same.

What Fear Is Asking You to Avoid

Fear has a useful function because it can alert us to genuine danger. The difficulty begins when the nervous system treats uncertainty and discomfort as though they carry the same significance as actual threat.

Gregory’s distinction is important. Many of the things people postpone are not dangerous. They are uncomfortable. That discomfort can still be powerful enough to influence behavior, particularly when we have become accustomed to protecting ourselves from uncertainty. His approach is to examine that reaction and, when the situation is safe, turn toward what creates discomfort rather than automatically moving away from it.

Scott has encountered the same dynamic through his practice of engaging strangers. He describes buying coffee for people and starting conversations while waiting for their orders. Even after doing this hundreds of times, he says there is still uncertainty because he cannot know how another person will respond. Yet the overwhelming majority of those encounters became positive experiences. The conversations often began with simple questions about who someone was and what was exciting them in life.

That experience illustrates something important about courage. Repetition does not necessarily eliminate uncertainty. Instead, it can change our relationship with uncertainty. We learn through experience that discomfort can be tolerated, that awkwardness does not have to become catastrophe, and that an action we initially resist can sometimes lead somewhere unexpectedly meaningful.

The question, then, becomes less about how to eliminate fear and more about understanding what fear is preventing us from discovering.

In this episode, you’ll learn

Why asking and answering difficult questions can itself be an act of courage
How meaningful questions reveal the fears, assumptions, and stories that shape our choices
Why vulnerability can transform an ordinary exchange into genuine human connection
How small acts of courage can gradually expand what you are willing to do
Why some of the most important things we accomplish happen before we feel ready
Which deeply human questions may be better explored with another person than outsourced to AI

Why Small Acts of Courage Matter

The most sustainable form of courage is often built through actions that appear insignificant from the outside.

Gregory describes courage as a kind of muscle that develops through repeated steps. Scott’s experiences with strangers illustrate the same principle from another direction. Each conversation is small, but every conversation provides another opportunity to practice moving through uncertainty.

There is also value in learning to recognize these moments after they happen. Gregory points out that people do courageous things regularly without necessarily interpreting them as courage. When we notice those actions and acknowledge them, we begin developing a more accurate understanding of what we are capable of doing.

This changes the way personal growth can be understood. Courage does not have to arrive as a new personality. It can develop through accumulated evidence. You ask the difficult question. You have the conversation. You make the decision. You discover that you were able to tolerate the uncertainty. The next time, you have that experience available to you.

Over time, the boundary of what feels possible can expand.

The Book That Started With a Question

There is a personal history behind The Book of Questions: Courage that makes the collaboration between Gregory and Scott particularly meaningful.

Scott tells John that his mother carried a dog-eared copy of Gregory’s original The Book of Questions in her purse when he was a teenager. His family used the book during gatherings, and for Scott, those conversations became an important experience of being heard. He describes himself as a shy kid who often lived an invisible life at school, yet around the family table, the questions gave him a voice and allowed him to feel that his opinions mattered.

Years later, Scott met Gregory on Zoom. As their friendship developed, they discovered an almost improbable overlap in their work. Gregory had spent decades pursuing the art of designing questions. Scott had spent much of his life exploring courage. Eventually, the obvious question emerged: what would happen if they brought those two disciplines together?

Their answer became The Book of Questions: Courage.

Scott explains that the questions were repeatedly tested between the two of them. They would take a question apart, discuss it, reformulate it, and bring their own experiences and vulnerabilities into the process until they reached what they felt was the essence of the idea.

That process helps explain why the book functions differently from a collection of advice. The questions are designed to create conversations rather than conclude them. Gregory describes the ideal question as one that leads to more questions, greater openness, and further exploration.

Scott has already seen what happens when one of those questions enters an ordinary family dinner. One question can keep people talking for an hour about things that matter to them. That is perhaps the most fitting description of the book’s purpose: it creates an opening, and then allows the people in the room to determine where the conversation goes.

Why You Shouldn’t Wait Until You Feel Ready

Near the end of the conversation, Scott chooses the final question in the book as the question that best captures the nature of courage:

“What is something extraordinary you’ve done and done well before you felt either ready or confident?”

His reasoning is revealing because it challenges one of our most persistent assumptions about action. We often imagine that confidence precedes meaningful behavior. We tell ourselves that once we have acquired enough knowledge, developed enough skill, or become sufficiently certain, we will finally be ready to act.

Scott’s experience suggests that the sequence often works differently. Many of the extraordinary things we do happen before we possess that feeling of readiness. Remembering those experiences can change how we interpret uncertainty in the present. Instead of seeing a lack of confidence as evidence that we should wait, we can recognize it as a familiar part of beginning something that matters.

Gregory follows the idea with another simple question: what is something courageous you have done this week?

That question brings courage back to the scale of everyday life. It asks us to notice the evidence that is already there. Perhaps courage has appeared in a conversation, a boundary, a decision, an apology, a creative risk, or a moment when we chose to act despite uncertainty.

The larger lesson is not that readiness is irrelevant. It is that readiness is not always a prerequisite for action. Sometimes we understand what we are capable of only after we have taken the step.

A Practical Experiment: Ask One Question You Have Been Avoiding

Choose one question that you have been postponing because you suspect the honest answer might require something from you.

Write the question down and answer it without trying to make the response more comfortable.

Then ask yourself one final question:

What is one small action I can take this week based on what I just learned?

Keep the action concrete and manageable. The purpose is not to resolve your entire life in one exercise. It is to turn reflection into movement.

When Questions Become a Way of Making People Matter

Gregory Stock and Scott Simon approach courage from different angles, yet their work converges on something deeply connected to John R. Miles’s The Mattering Effect. Gregory shows how meaningful questions help us uncover what people truly value, while Scott demonstrates how the courage to ask and answer those questions can create deeper human connection.

That connection sits at the heart of mattering. When we genuinely listen to someone’s answer, invite their story, and give them space to be vulnerable, we communicate something powerful: you are seen, your experience matters, and your presence has significance.

John’s upcoming book, The Mattering Effect: Creating a Life of Meaning and Worth, explores that deeper science of feeling seen, valued, and needed. The book releases October 6, 2026, and follows his Passion Struck, which was previously selected as a Next Big Idea Club Must-Read.

As The Mattering Effect joins the Next Big Idea Club’s 2026 Must-Read conversation, this episode offers a fitting place to begin exploring the idea: sometimes the simplest way to help someone feel that they matter is to have the courage to ask a better question, and then truly listen to the answer.

Discover more about The Mattering Effect and John’s work at thematteringeffect.com

FAQ (Frequently Asked Questions)

How do you build courage?

You build courage through repeated experiences of taking meaningful action while tolerating uncertainty or discomfort. Gregory Stock describes this as developing a small courage muscle through incremental steps, while Scott Simon emphasizes deliberately practicing behaviors that move beyond familiar comfort zones.

Can asking questions help you build courage?

Yes. Asking a difficult question can require us to confront something we would rather avoid, while answering it honestly can require even greater vulnerability. Scott describes the ability to ask and answer hard questions as one of the central challenges he encounters in his work with courage.

What question can reveal what is holding you back?

One of the questions Scott discusses is, “What is one lie you are telling yourself to keep yourself safe, but is really holding you back?” The question encourages people to examine protective narratives that may once have served a purpose but now restrict their choices.

What is the connection between courage and vulnerability?

Courage and vulnerability often meet when we reveal something meaningful without knowing how another person will respond. Scott describes the experience of asking and answering difficult questions with others as a process that can move people from discomfort toward connection.

Why do people wait until they feel ready?

Readiness can feel like a form of protection because it suggests that uncertainty will disappear once we have enough confidence, knowledge, or preparation. Scott’s reflection on the final question in the book suggests that many meaningful accomplishments happen before that feeling arrives.

What are small acts of courage?

Small acts of courage are ordinary decisions that require us to move through manageable discomfort because something matters to us. They can include initiating a difficult conversation, asking a vulnerable question, trusting your judgment, approaching someone new, or taking action on something you have been postponing.

How can questions create deeper relationships?

A thoughtful question can give another person permission to share experiences, memories, values, and emotions that ordinary conversation may not reach. Gregory describes questions and storytelling as a process in which each response can create another question, allowing a conversation to become progressively more personal and meaningful.

What questions should we keep uniquely human in the age of AI?

Scott argues that questions involving deep human emotion and lived experience deserve particular care. He explains that when he and Gregory develop questions, they bring their own histories, vulnerabilities, and passions into the process. Gregory adds that AI can generate prompts quickly but does not yet understand the human experiences that give profound questions their depth.

What is one question I can ask myself today?

A useful starting point comes from the final question Scott chose from the book: “What is something extraordinary you’ve done and done well before you felt either ready or confident?” The question encourages you to look backward for evidence that you have already acted courageously before certainty arrived.

How can I practice courage this week?

Choose one small action that you have been postponing because it feels uncomfortable rather than genuinely dangerous. Then take that action before you feel completely ready. The purpose is to create an experience that teaches you something about your own capacity to move through uncertainty.

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