In this episode of Behavior Gap Radio, Carl explores the difference between kind and wicked learning environments—and why misunderstanding feedback can lead us to learn exactly the wrong lesson. Drawing on examples from markets, backcountry skiing, and life decisions, he explains how delayed or unreliable feedback can turn experience into overconfidence instead of wisdom. Carl shows why outcomes aren’t always feedback, why “nothing bad happened” can be dangerously misleading, and why strong processes matter more than results in wicked environments. A crucial guide to learning safely in uncertain terrain.

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In this episode of Behavior Gap Radio, Carl explores how many of our worst decisions come from playing the right game on the wrong clock. Time horizons shape how we interpret risk, success, discomfort, and progress—but most of us mix up short-term and long-term games. Carl explains why impatiently “digging up the oak tree” to check the roots derails meaningful work, how long-term thinking reveals signal over noise, and why borrowed timelines create borrowed anxiety. Align the clock with the game, he says, and you give your decisions—and your life—the chance to compound.

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In this episode of Behavior Gap Radio, Carl tackles an uncomfortable truth: Luck plays a bigger role in our lives—and our outcomes—than we like to admit. He explains why, in complex environments like markets, careers, and relationships, good decisions can lead to bad results and bad decisions can occasionally pay off. Through stories, including a man who gambled everything on one roulette spin, Carl illustrates the crucial distinction between skill and luck, and why the real work is building a repeatable decision-making process. Recognizing luck, he says, brings humility, compassion, and clearer thinking in uncertain terrain.

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In this episode of Behavior Gap Radio, Carl unpacks the idea of sense-making—the way we build just enough coherence from past events to take the next step in uncertain environments. Through a story from his New York Times days and reflections on how we interpret unexpected outcomes, he explains that sense-making isn’t about accuracy or perfect explanations. It’s about crafting a plausible story that helps us move forward. Carl shares the questions he uses to check his own stories—What am I noticing? What am I ignoring? Does this story help me act or trap me?—and reminds us that in complex, adaptive systems, story isn’t a luxury. Story is navigation.

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In this episode of Behavior Gap Radio, Carl breaks down one of the most important ideas in decision-making: the difference between simple, complicated, and complex systems. He explains why mislabeling the terrain you’re navigating—whether in markets, mountains, creative work, or relationships—leads to using the wrong tools and taking the wrong risks. Through stories ranging from bestselling authors to early climbing mistakes, Carl shows why checklists fail in complex environments, why expertise can become a liability, and why navigating uncertainty requires experiments, awareness, and reducing exposure. A foundational lesson in seeing the world as it really is.

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In this episode of Behavior Gap Radio, Carl breaks down three words we often mix up when thinking about risk: danger, exposure, and vulnerability. Through a story about an elderly client worried about geopolitical news that had no real impact on her, he shows how easy it is to confuse “danger out there” with “risk to us.” Carl explains why understanding where the danger truly is, how exposed we are to it, and how vulnerable we’d be if it hits, can completely change our decision-making in markets, mountains, and everyday life.

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In this episode of Behavior Gap Radio, Carl shares a sobering story about mountain risk—and how it reshaped the way he thinks about uncertainty in every area of life. After reading an avalanche accident report, he realized that what he’d been calling “experience” was often just luck. From backcountry skiing to investing to the boardroom, Carl explains three practices that now guide his decisions: respect uncertainty, pay attention to small signals, and reduce exposure so the leftover risk can’t destroy you. A powerful reflection on seeing risk clearly and staying alive to learn from it.

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In this episode of Behavior Gap Radio, Carl tackles the hype and fear swirling around the “Magnificent Seven” stocks and the temptation to either go all-in or get out entirely. He explains why a disciplined investor doesn’t chase hot names—or panic when a single stock grows to 7.5 percent of the S&P 500. Instead, they rebalance based on allocation, not predictions. If something grows beyond its intended weight, you trim it—not because you’re smart enough to call the top, but because it’s out of balance relative to your goals and values. A clear, grounded take on investing like an adult.

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In this episode of Behavior Gap Radio, Carl revisits one of the most striking examples of the behavior gap: Peter Lynch’s legendary Magellan Fund. While the fund returned an extraordinary 29 percent, the average investor captured only a fraction of it—and some studies say many even lost money. Why? Because humans buy high, sell low, and chase what’s hot. Carl breaks down how this pattern shows up again and again, why even great investment processes fail if behavior doesn’t support them, and why the real challenge isn’t finding the best fund… it’s staying in it.

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In this episode of Behavior Gap Radio, Carl returns to his roots and digs into the heart of investing: having a clear, defensible process. Whether you’re an advisor, a planner, or simply someone who invests, he challenges you to ask one simple question: Why are you invested the way you’re invested? Carl explains why relying on headlines, hype, or a single podcast won’t cut it—and why writing down your investment process, as if you had to defend it in a room full of smart people, might be the most important exercise you do before the next real test arrives.

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