Behavior Gap Radio

In this episode, Carl explores the productive tension between problem-to-solve planning and purpose-based planning, and why great planning requires moving fluidly between both. He explains how advisors should meet presenting problems with real empathy while quietly listening for deeper signals about purpose, meaning, and values beneath the surface. The work, he argues, isn’t choosing one approach over the other. It’s serving the human in front of you, solving what hurts right now, and gently guiding the conversation toward why any of it matters in the first place.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl reframes planning as a living practice rather than a one-time event, arguing that the real work of planning is the ongoing process of aligning your use of capital with what matters most as life and priorities change. He explores how treating plans as fixed predictions creates pressure, shame, and anxiety, while viewing planning as a rhythm of orienting, acting, learning, and adjusting allows us to stay grounded in reality. Planning, he suggests, isn’t about being right forever. It’s about being a little less wrong over time and building a sustainable way to navigate uncertainty.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl challenges the idea that resilience is about toughness or enduring pain, arguing instead that real resilience comes from thoughtful design that avoids unnecessary exposure in the first place. Using a powerful backcountry skiing analogy, he explains how shifting from managing danger to choosing safer terrain reframed his understanding of risk, joy, and sustainability. The lesson carries directly into planning and life: Resilience isn’t about surviving fragile systems through grit, but about building plans with margin and guardrails so failure is survivable and courage isn’t constantly required.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl expands the idea of planning beyond money to include the four forms of capital we’re always spending: money, energy, time, and attention. He explains why plans that only optimize for dollars can look great on paper and still fail in real life, especially when invisible costs like exhaustion, distraction, or resentment go unexamined. Through simple, human examples, Carl argues that attention is the true currency of meaning and relationships, and that real planning is about aligning how we use all of our capital with what actually matters to us.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl reframes optionality as one of the most important forms of safety in planning. Pushing back on the romantic idea of “burning the boats,” he explains why removing all alternatives doesn’t create commitment; it creates fragility. In an uncertain world, optionality is the ability to respond to new information, not a sign of fear or indecision. Through ideas like micro-actions, Slack, and margin of safety, Carl shows how small, reversible steps create learning, resilience, and real momentum. This is a conversation about designing plans that can bend instead of break, and why flexibility, not drama, is what actually carries us forward.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl introduces the idea of the “next local optimum” and challenges the fantasy that meaningful change comes from one big, heroic leap. In complex, real-world systems like money, careers, and relationships, clarity doesn’t arrive before action. It emerges because of action. Carl explains why small, reversible steps matter more than bold plans, how micro-actions create learning and reduce risk, and why navigation beats ambition every time. This is an episode about trading certainty for orientation, letting go of the myth of the big move, and learning to trust the quiet power of the next small step.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl pauses his planning series to explore the idea behind one of his favorite sketches from his new book: The Four Sources of Capital. Prompted by a thoughtful LinkedIn question, he unpacks why money, energy, time, and attention deserve to be treated as distinct—and why attention may be the most valuable of all. Using a simple skiing example, Carl shows how we can spend money, time, and energy without ever really being present, and how attention is what turns activity into meaning. At its core, this episode is a reflection on why attention is the true currency of meaningful experiences and lasting relationships.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl turns the planning conversation toward current reality and asks a deceptively simple question: Where are you, really? After starting with purpose, values, and goals, he explains why honest planning can only begin once we locate ourselves clearly. Carl reframes balance sheets and net worth as stories, not just numbers, and shows why naming what you own and what you owe is an act of kindness, not judgment. This episode explores how radical honesty, done slowly and without shame, can turn vague anxiety into something workable and gives planning a real place to start.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl introduces the idea of “crunchy bits” and emotional resonance—those subtle moments in a conversation when something important is trying to surface. He explains how to notice the signals: changes in tone, pauses, defensiveness, laughter, body language, or even a shift you feel within yourself. Most importantly, Carl talks about the courage to slow down and hold space, rather than rushing past discomfort. This episode serves as a practical guide to the fine-brush work of real financial planning, where presence, patience, and trust create the conditions for meaning to emerge.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl explores how real financial planning conversations actually deepen. While initial questions matter, they’re only the doorway. The real work begins after the first answer. Carl introduces the idea of “go-deeper transitions”: simple, human moves like saying “tell me more,” noticing emotionally charged words, or gently naming what feels important in the room. He explains why these moments matter more than perfectly scripted questions, and how curiosity, presence, and permission allow deeper meaning to surface over time. This is a practical look at how listening turns a surface conversation into one that actually changes how people understand money and their lives.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl names the core skill at the heart of real financial planning: listening. Not just hearing words, but practicing presence, intuition, and sensing what’s actually happening in the room. He explains why this kind of listening isn’t taught in traditional financial planning and why it can feel uncomfortable, vague, and hard to measure. Through simple, everyday examples, Carl shows how listening and trusting intuition are skills you can practice, and why letting go of false certainty is essential. This episode is about reclaiming listening as the real craft of planning, and why it matters more than any spreadsheet ever could.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl reframes the role of the planner in what he calls real financial planning. The job isn’t to calculate or construct meaning, but to facilitate its discovery. Using the metaphors of archaeology and non-destinational hiking, Carl explains why meaning already exists within the client, and why the planner’s work is to uncover it with presence, care, and skill. Spreadsheets and models still matter, but only as tools that create space for deeper exploration. At its core, this kind of planning is about guidance, facilitation, and learning how to get out of the way so something more meaningful can emerge.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl makes a clear and challenging claim: Real financial planning can only happen in conversation—not in forms, intake sheets, or tools, and not even in artificial intelligence. This kind of planning lives in human dialogue, where safety, permission, and space are created to explore what actually matters. Carl explains why money questions become a doorway to deeper work, why this isn’t therapy or meditation (though it borrows tools from both), and why planning is ultimately a relational, conversational act. If meaning is the goal, conversation is the only place it can be found.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl shares a pattern he’s seen hundreds of times: people who’ve “won the game” financially, yet quietly ask, "Is this all there is?" He uses these conversations to explain a core idea in real financial planning. Clients rarely come in asking for meaning or alignment. They arrive with a presenting problem about money. But beneath that surface request is a desired future state they often don’t yet have language for. Carl argues that the real work isn’t dismissing the money question, but meeting it with empathy and using it as an entry point to something deeper. This episode explores the gap between solving financial problems and helping people uncover the life they were actually hoping those solutions would lead to.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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, pointing out that rising financial anxiety suggests something is off. This conversation isn’t about neat metrics or proving value with spreadsheets. It’s about aligning the use of capital with what truly matters, leaning into the ambiguity, and trusting that meaning is something you recognize when you feel it.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 about aligning how you use your capital, time, energy, and attention with what actually matters to you, so you can live a more meaningful life. The label is imperfect, but the distinction matters. This episode lays the philosophical spine for the practical work that follows.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 evolve without shame. Carl shares client stories to illustrate how purpose anchors goals, keeps them from becoming brittle, and reminds us that the point was never the goal itself. The point was living in alignment with what matters in the real world, where plans change and clarity is always provisional.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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, and creates coherence over time, especially when trade-offs show up or conditions change. It doesn’t eliminate fear or guarantee outcomes. It simply gives you a heading when the path isn’t clear and reminds you how to decide when you don’t know.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 creates coherence, durable direction, and meaningful constraints that make trade-offs clearer without making them easy. Purpose can’t be forced under threat, but when there’s space for it, it helps us choose which problems are actually worth solving and how we want to live while solving them.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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: What are we actually solving for right now? When used well, it stabilizes the situation, reduces anxiety, and restores enough clarity and bandwidth to move forward. Sometimes the wisest plan is simply getting the arrow out of your arm.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 (how it shows up), and goals (temporary, adjustable guesses), Carl shows how planning becomes calmer, more flexible, and more human. Start with purpose, let goals emerge, and allow plans to adapt without shame.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 create a quiet gravitational pull toward what matters, and they offer hope when certainty isn’t available. Goals don’t lock us in. They help us keep moving.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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, adaptation, and course correction, where change signals insight, not failure. The real value of a plan is orientation, flexibility, and a clear way forward in uncertain terrain.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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, and remain aligned with what matters most as conditions change. This episode sets the stage for a deeper look at planning as an operating manual for navigating reality.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 inviting the most intimate form of feedback there is. Carl explains why that fear makes sense, why it can’t be eliminated, and why the only real option is to feel it fully… and do the work anyway.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 but a risk-management strategy. In a complex, adaptive world, planning isn’t about control or prediction. It’s an ongoing practice of awareness, flexibility, and learning to work with what inevitably shows up.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 assume experience equals insight, and why better questions—about feedback, time horizons, and the role of luck—matter more than confident conclusions.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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 reframes the frustration of constantly adjusting plans as a feature of reality, not a personal failure, and sets up the questions that come next about learning, feedback, and making decisions in a world that won’t sit still.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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, but as a feature. That’s where the real work begins.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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. Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

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.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this short episode of Behavior Gap Radio, Carl reflects on how easy it is to drift into tracking the wrong metrics—the ones the world cares about, not the ones that actually matter to you. When your attention slips to measures that don’t align with your values, things get messy. The antidote is simple but essential: get clear on what matters, then measure only that.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this Field Note episode of Behavior Gap Radio, Carl shares a real-time lesson from the chaos of airline travel during his book tour. When you’re navigating a complex adaptive system—whether it’s airports, markets, or major life decisions—the key variable is information. Carl walks through how to gather what you can, when to stop analyzing, and how to take small “micro-actions” designed to generate the highest-quality information for your next move. A short, practical reminder for anyone facing uncertainty.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode of Behavior Gap Radio, Carl explores what he calls the discipline of more—or what he sometimes calls the bigger yes. Instead of fighting bad habits through willpower, he suggests crowding them out by filling life with things you love. From moving woodchips under a headlamp to swapping screen time for saunas and books, Carl shares how choosing a “bigger yes” creates space for what matters—and quietly leaves no room for what doesn’t.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode of Behavior Gap Radio, Carl shares a favorite quote from explorer Rick Ridgeway: “The best journeys answer questions we never thought to ask.” He reflects on what that really means—that the purpose of a journey isn’t to chase answers, but to discover better questions along the way. Whether it’s a mountain adventure, a creative pursuit, or the quiet work of introspection, Carl asks: How can we systematically put ourselves at risk for good things to happen?Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode of Behavior Gap Radio, Carl introduces a phrase he’s been searching for: ecological naïveté—the idea that our instincts were perfectly suited for a world that no longer exists. Using examples from nature and investing, he explains why our ancient wiring makes us want to run from market drops and chase safety, even when we know better. The takeaway? You’re not a bad investor—you’re just human. The work isn’t to fight those instincts, but to notice them with compassion and patience.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this Field Note episode of Behavior Gap Radio, Carl shares a simple but powerful practice: extreme assumption questioning. From $5 million sailboats to retirement goals and client meetings, he shows how many of our “facts” are really just unexamined beliefs. By treating assumptions like a game—asking, “What if this isn’t true?”—we create the space for new, creative possibilities to emerge.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode of Behavior Gap Radio, Carl explores what he calls “big stupid human tricks”—the kinds of goals that force us to grow into new people. But instead of running a marathon or climbing a mountain, he wonders if the hardest challenge might actually be internal. What if the real adventure is a silent retreat, putting your phone away, or sitting quietly with yourself? Carl reflects on how the scariest terrain to navigate isn’t out there—it’s in your own heart.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode of Behavior Gap Radio, Carl digs into a simple but unsettling truth: After the fact, randomness always looks like strategy. He unpacks the concept of retrospective coherence—our tendency to turn chaos into neat career stories—and how that illusion feeds “success porn” by hiding the messy role of luck and timing. From startups to financial advice, Carl reminds us that most of what looks like a master plan was really just stumbling into survival.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

Carl’s back on Behavior Gap Radio with a quick, honest update. He shares what the past week of book launch conversations taught him about defining success, why he briefly felt like an imposter, and the big goal that matters most: more meaningful conversations about money. He also gets practical with three clear invites—book him for your show or channel, leave an Amazon review, and order a copy from your local bookstore—and previews what’s next here: putting yourself at risk, making decisions under uncertainty, and choosing which creative projects to pursue.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

I’ve been wrestling with a question for years: Why do I always call Jason? Jason is a friend of mine who always affirms my ideas.This essay and sketch was my attempt to confront confirmation bias head-on. We’re wired to seek agreement. But that’s how bad decisions happen.In this episode of Behavior Gap Radio, I share the story behind it, and how I try to push myself to invite dissonance instead of comfort.This sketch is #92 in the new book. It’s called Stop Calling Jason. You’ll find it in ​Your Money: Reimagining Wealth in 101 Simple Sketches​, coming October 21, 2025.If you want a preview, I’ve put together a beautifully designed excerpt with seven of my favorite essays and sketches.📩 Just email [email protected] with the subject line "Friend of Carl" and we’ll send it to you.You can pre-order the book now. My recommendation? Order one copy from ​Amazon​ and one from ​your favorite local bookstore​!• Amazon• Local bookstores• Bulk orders (25+ copies): Don't forget to use code YourMoney5 at checkout for an additional 5% off the already discounted bulk order pricing! We held a special book launch conversation on September 30 with New York Times money columnist Ron Lieber. If you missed it live, good news: 🎥 ​Watch the full recording here: https://www.youtube.com/watch?v=n7PEAeb4n_4& We hope it sparks some meaningful conversations for you and those you care about.