Behavior Gap Radio

In this episode, Carl pushes deeper into a core tension of real financial planning: if it’s not about money, what are we actually measuring? His answer is uncomfortable and deliberate. Meaning is the output, even though it’s hard to quantify, difficult to compare, and impossible to reduce to tidy units. Carl challenges the profession’s habit of measuring what’s easy instead of what matters, pointi...

In this episode, Carl gets more concrete about what he means by real financial planning. Prompted by repeated questions of “yes, but how do you actually do it?” he defines the strain of planning he cares most about and what sets it apart. The core idea is simple but radical: money is not the outcome, meaning is. Money is a tool, not a scoreboard. Real financial planning, as Carl frames it, is abou...

In this episode of Behavior Gap Radio, Carl explains why goals should grow out of purpose, not the other way around. Rather than starting with numbers or aspirational targets, he shows how a clear sense of purpose gives goals meaning, flexibility, and durability. When goals emerge from purpose, they stop feeling like pressure or performance metrics and start acting as directional markers that can...

In this episode of Behavior Gap Radio, Carl walks through how to write a Statement of Financial Purpose and why it matters more than values lists, slogans, or motivation. Drawing from personal experience and years of planning work, he explains how a clear purpose acts as an orientation device, not a prediction or a pep talk. A good statement of purpose narrows choices, reduces decision fatigue, an...

In this episode of Behavior Gap Radio, Carl explores purpose-based planning, a quieter, more orienting mode of planning that becomes possible once the fires are out and there’s enough stability to think clearly. Unlike problem-to-solve planning, which demands immediate solutions, purpose-based planning asks a deeper question: What do I want this plan to be in service of? Carl explains how purpose...

In this episode of Behavior Gap Radio, Carl introduces problem-to-solve planning, a practical mode of planning meant for moments of urgency, constraint, or pain. Drawing from stories in the mountains, the ER, and years of reader questions, he explains why some situations don’t call for deep purpose or big-picture reflection. They call for action. Problem-to-solve planning asks one clear question:...

In this episode of Behavior Gap Radio, Carl shares an essay on purpose, values, and goals, and why so much anxiety around planning comes from starting in the wrong place. He explains how goals feel brittle and high-pressure when they’re mistaken for purpose, and why missing a goal can feel like a personal failure when the deeper “why” isn’t clear. By untangling purpose (the enduring why), values (...

In this episode of Behavior Gap Radio, Carl asks a fair question: If the world is uncertain, and plans are just guesses, why have goals at all? He reframes goals not as promises or predictions, but as values-informed guesses that relieve pressure instead of creating it. Carl explains the three reasons goals still matter in an uncertain world: they give us direction when the path isn’t clear, they...

In this episode of Behavior Gap Radio, Carl continues his exploration of what a plan actually is—and what it isn’t. A plan, he argues, is a hypothesis: a best guess worth testing, not a promise or a prediction. When we treat plans like guarantees, we invite overconfidence at the start and panic when reality inevitably changes. Instead, Carl reframes planning as an ongoing process of learning, adap...

In this episode of Behavior Gap Radio, Carl begins exploring a deceptively simple question: What is a plan, really? After weeks of unpacking risk, uncertainty, and the limits of prediction, he reframes planning as a living practice—not a promise, forecast, or static document. In a world that isn’t stable or fully knowable, a good plan acts as a working model that helps you adapt, stay oriented, an...

In this bonus episode of Behavior Gap Radio, Carl reflects on a conversation with an entrepreneur facing what she described as “terror” on the edge of launching deeply personal work. He explores the difference between building something as a business case and creating something as art—and why the latter carries a unique kind of risk. When you say, “Here, I made this. I hope you like it,” you’re in...

In this episode of Behavior Gap Radio, Carl shares Essay #4 in his ongoing series and reframes one of the most misunderstood ideas in planning: risk. Most of what we call risk isn’t volatility or headlines—it’s what’s left over after you think you’ve planned for everything. Carl explains why good plans don’t eliminate risk, why certainty should make us nervous, and why humility is not a weakness b...

In this episode of Behavior Gap Radio, Carl revisits the critical difference between kind and wicked learning environments—and why experience can either make you wiser or dangerously overconfident. When feedback is clear, fast, and reliable, learning compounds, but when feedback is delayed, noisy, or misleading, experience can quietly teach the wrong lessons. Carl explains why real planning can’t...

In this episode of Behavior Gap Radio, Carl digs into one of his core ideas: You don’t solve the world you’re in, you navigate it. Building on the first essay, he explains why so much planning advice quietly assumes a linear, controllable world—and why that breaks down in the complex adaptive landscapes where most of life actually happens. From careers to relationships to raising kids, Carl refram...

In this episode of Behavior Gap Radio, Carl introduces the first essay in a new series, The World Is Not What We Were Promised. He reflects on the quiet assumptions many of us absorb about how life is “supposed” to work—and what happens when reality doesn’t cooperate. Rather than fighting uncertainty, Carl suggests adopting a posture of living in wrongness and treating uncertainty not as a flaw, b...

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 a...

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...

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, Ca...

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 th...

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 author...

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 ar...

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:...

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 it...

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...

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...