Behavior Gap Radio

Risk is just a concept—until it isn’t. This week, Carl shares a backcountry ski adventure that took an unexpected turn, turning a routine 25-minute descent into a five-hour lesson in risk, preparation, and the power of community. What happens when risk stops being theoretical and shows up in real life? And how does that apply beyond the mountains—to investing, business, and creative work?

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In this episode of Behavior Gap Radio, Carl revisits the purpose of goals—why we set them, why they’re often just guesses, and why we should still have them anyway. He explores how goals provide a sense of direction and create a gravitational pull that helps us recognize opportunities. But a recent conversation introduced a third, unexpected reason: hope. What if setting a goal isn’t just about achievement but about creating something to look forward to?

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In this episode of Behavior Gap Radio, Carl unpacks the irony of our most well-intentioned distractions—especially when they become clever ways to avoid the real work. From obsessively reading time management books to spending hours researching the best apps to reduce screen time, Carl explores the sneaky ways we hide from what actually matters. What if the solution isn’t another tool or strategy but simply doing the thing we’ve been avoiding?

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In this episode of Behavior Gap Radio, Carl unpacks the power of visual shortcuts and meaningful souvenirs—how his sketches distill complex ideas into simple, conversation-starting icons. He shares an essay from his upcoming book, Your Money: Reimagining Wealth Through Simple Sketches, exploring the foundational idea that a plan must come before anything else. Too often, we obsess over products—stocks, credit cards, investments—without first deciding where we’re headed. Through his well-known sketch, The Plan Comes First, Carl explains why products only make sense in the context of a plan and how visuals serve as both a shortcut to understanding and a lasting souvenir of a learning experience.

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In this episode of Behavior Gap Radio, Carl dives into the never-ending search for purpose. Once believing he'd eventually find his purpose and be done searching, he now sees the search itself as the point—the driving force of his life. He explores how we can be both content and striving, fulfilled and still growing, holding both truths at the same time. What if purpose isn’t something to capture but something to keep discovering?

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In this episode of Behavior Gap Radio, Carl explores the paradox of being content in his discontent—the idea that growth, searching, and pushing boundaries don’t have to come from a place of dissatisfaction. He wrestles with the tension between striving for more and embracing the present moment, questioning where the line is between creative curiosity and restless grasping. Can we hold both? Is the desire to explore something to be resolved or something to be cherished?

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In this episode of Behavior Gap Radio, Carl shares an essay titled Range of Outcomes from his upcoming book—a simple sketch that captures the messy, uncertain, and unpredictable nature of the future. He explores the tension between fear and excitement and how we chase certainty but could instead embrace mystery, adventure, and surprise. Some days, uncertainty feels overwhelming, while on other days, it feels exhilarating. Both are true. Both are human.

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In this episode of Behavior Gap Radio, Carl poses a simple yet powerful question: What’s your earliest memory of money? He explores how this question can unlock deep conversations, from childhood experiences to the emotions tied to financial moments. Whether it's recalling a childhood paper route or the tension of overheard arguments, these memories shape our relationship with money. Carl encourages listeners to try asking the question—especially with kids—and to embrace the conversations that follow.

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In this episode of Behavior Gap Radio, Carl dives into why he’s writing another book—Your Money: Reimagining Wealth Through Simple Sketches—and what drives the project. He sees books as tools for meaningful conversations, whether around the dinner table, on a walk with a partner, or in an advisor’s office. He shares his ambitious goal of sparking a million conversations a month and gives a behind-the-scenes look at upcoming book launch plans, from virtual chats to live events.

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In this episode of Behavior Gap Radio, Carl unpacks the surprising power of goals—even when they’re just guesses. He shares a personal financial goal and how setting a clear target creates both direction and an almost magical gravitational pull that brings new opportunities into focus. From cutting unnecessary subscriptions to resisting impulse purchases, he explores how small choices compound into real progress. If you've ever questioned whether goals matter, this episode might just change your mind.

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