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

What if the question you’re avoiding is the one you most need to answer?
We often think courage means doing something difficult or frightening. But Scott Simon says the place people struggle most isn't physical courage—it’s having the courage to ask and answer hard questions.
In this episode, Scott Simon and Gregory Stock bring together two decades-long bodies of work: Scott’s exploration of courage and Gregory’s groundbreaking Book of Questions, which became a New York Times bestseller and sold millions of copies.
Their new book, The Book of Questions: Courage, is built around a simple idea: the right question can take you beneath the surface of your life and reveal what you actually believe, fear, want, and value.
And sometimes, one honest question can change the direction of your life.
In this conversation, we explore:
• Why asking yourself a hard question can require more courage than taking action
• The question Scott says cuts directly to the core: What lie are you telling yourself to keep yourself safe that is actually holding you back?
• Why great questions don't give you answers—they create space for self-discovery
• How vulnerability can make people feel more connected rather than more exposed
• Why one meaningful question can turn an ordinary dinner into an hour-long conversation that people remember
• Why we often avoid deeper conversations even with the people we know best
• What we're losing in an increasingly distracted, answer-rich world
• Which questions we should deliberately refuse to outsource to AI
• Why AI can provide information but still cannot tell us who we want to become
• The question Scott believes everyone should ask: What is something extraordinary you've done well before you felt ready or confident?
One of the most powerful ideas in the conversation is that a good question doesn't close a conversation—it opens one. So before you move on with your day, ask yourself:
What is one question I've been avoiding because I already suspect I know the answer? That might be where your next chapter begins.
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