Behavior Gap Radio: Exploring human behavior...with a Sharpie

In this episode, Carl shares a small but revealing moment of failure. After spending most of the day resisting the urge to do the “checky check,” he slipped late at night and lost nearly an hour wandering the internet. Instead of turning that mistake into a story about personal failure, Carl explores a different response: treating the moment as information. By noticing the pattern, getting curious about the behavior, and simply beginning again the next day, he reflects on a gentler and more productive way to relate to mistakes.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 reflects on what he calls the “checky check,” the familiar habit of reaching for quick dopamine hits by checking news, social media, or email whenever work gets hard or energy drops. Lately, he's been interrupting that impulse with a simple reminder: “There's nothing for you there.” The idea isn't about discipline for its own sake, but recognizing that the relief we're looking for in those moments usually isn't found in another quick scroll. Sometimes the most helpful move is simply noticing the impulse and choosing something better instead.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 simple “conversation toolbox” for moments when someone asks for advice. Often, people don't actually need answers as much as they need space to think through their next step. Carl explores a few practical ways to stay present in those conversations—acknowledging that something is hard, asking whether the person wants advice or simply to be heard, and using thoughtful questions to help them uncover their own answer. The goal isn't to rush to solutions, but to create the conditions where clarity 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 explores the idea of “red flag behavior,” the personal patterns that show up when we're under pressure and facing uncertainty. Borrowing a lesson from backcountry skiing, Carl explains how knowing your own weak spots—your “kryptonite”—can help you put guardrails in place before a risky decision happens. Whether it's impulsivity, rushing to closure, or offering quick advice just to escape ambiguity, recognizing these patterns is the first step toward making better decisions when the stakes are high and the future is unclear.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 reflects on a recent conversation with members of The Collective and explores a powerful idea about leadership and advice. Instead of rushing to provide answers, great leaders create the conditions and containers for honest conversation and shared understanding. Drawing on insights from Michael Bungay Stanier and Michael Hudson, Carl suggests that the real skill isn't dispensing advice too quickly, but asking better questions and helping people uncover the wisdom they already have. Sometimes the most valuable thing we can do is simply hold the space a little longer.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 brief but powerful reflection inspired by Marcus Aurelius. Drawing from Stoic wisdom, he reads a simple line and lets it stand on its own: “The only wealth which you will keep forever is the wealth you have given away.” Carl offers almost no commentary, inviting listeners to sit with the idea and consider what it might mean about generosity, meaning, and the true nature of wealth.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 the idea of “negative capability,” a term coined by John Keats to describe the ability to remain in uncertainty without rushing to easy answers. In a world that constantly pressures us to predict, forecast, and sound confident, Carl suggests that real wisdom may lie in something different: the capacity to sit with ambiguity long enough to make thoughtful decisions. Good decisions, he argues, don't require certainty. They require clarity about what matters and the courage to take the next small step—even when the future is unknown.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 reflects on a line often attributed to H. L. Mencken: "Every complex problem has a solution that is simple, direct, plausible—and wrong." Carl explores the tension between simplicity and complexity, and the discipline required to stay in the messy middle long enough to find what he calls “elegant simplicity.” Instead of rushing to easy answers, the real work involves living with ambiguity, cutting through layers of nuance, and gradually discovering the clarity that lies on the far side of complexity.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 striking teaching attributed to Jesus from the non-canonical Gospel of Thomas. The story describes a wealthy man carefully planning how to grow and store his wealth so he would never lack anything—only to die that same night. Carl reflects on how prophets, poets, and philosophers across centuries keep pointing to the same lesson: wealth can be useful, but it's wise not to become too attached to 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 reflects on the relationship between money and meaning. While money can help create the conditions for security, autonomy, and purpose, it can't actually deliver any of those things on its own. Carl explores how real security is often a nervous system issue, how autonomy still requires the choice to claim freedom, and how meaning grows from what we do with that freedom. The key insight is simple but powerful: money can create the space for these things to emerge, but experiencing them still depends on the choices we make.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 reflects on conversations with Olympic silver medalist Haley Batten and what it really means to perform at a high level. Watching the intention and discipline behind an Olympian's daily routine sparked a realization: high performance isn't just for elite athletes. Any of us can approach our own work and lives with the same mindset by focusing on small improvements each day. Carl explores the idea of designing your “ultimate day,” holding the tension between striving for excellence and accepting imperfection, and building a life where getting a little better each day becomes its own kind of Olympics.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 reflects on a thoughtful idea shared by financial planner Jack Boston: the longer the projection, the more humility we need around our assumptions. Whether we're building a financial plan, a business forecast, or simply making life plans, every projection relies on assumptions that will inevitably be wrong. Carl explores the danger of false precision, the importance of holding our projections loosely, and why planners should have a clear, defensible philosophy behind the assumptions they choose. The real work isn't pretending to be right, but staying humble enough to adjust when reality proves us wrong.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 simple practice for becoming more present in conversations: looking for what he calls the “crunchy bits.” These are the moments when the emotional texture of a conversation shifts—when someone uses a loaded word or reveals something that carries deeper meaning. By staying curious and paying close attention, Carl suggests we can learn to notice these moments and respond more thoughtfully. It's a small skill, but one that can transform how we listen, connect, and understand the people around 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 shares a simple but powerful reframing of a common question: “Can I afford it?” Whether it's a trip, a sabbatical, or a chance to spend time with someone you love, the real question often isn't just about money. It's also about the cost of regret. Carl suggests that when making these decisions, we should consider not only the price of going, but also the price of not going. Sometimes that perspective changes the math in ways we don't expect.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 brief reflection on the traditional idea of retirement. Outside of professions where physical limits make it necessary, he questions the notion of spending decades working at full speed only to stop completely one day. Instead, Carl suggests a different approach: designing work and a life you don't feel the need to escape from in the first place. For many people, that shift might take years to build, but the question is worth sitting with. What would it look like to create a life you don't need to retire from?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 continues the conversation about “risk hangover,” the emotional aftermath that can follow a painful financial loss. He explores common patterns that show up in that state, like overcorrecting, anchoring to old highs, shortening time horizons, or rushing to repair the damage. Carl also shares a simple recovery protocol: pause, separate emotions from the numbers, give your nervous system time to settle, and then reinstall thoughtful guardrails before making the next decision. The goal is not to avoid risk entirely, but to recover from it in a way that leads to wiser decisions next time.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 the idea of a “risk hangover,” the emotional aftermath that can follow when a big risk doesn't work out. It often shows up as regret, shame, rumination, or the urge to quickly “get back to even.” Carl reflects on how our brains treat financial mistakes as threats and how that can push us toward impulsive or avoidant behavior. The key, he suggests, is learning to recognize your personal red flags before making a risky decision. By understanding the patterns that show up when emotions run high, we can make wiser choices the next time risk appears.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 reflects on a simple but powerful signal: energy. After a long day of work, he noticed that some activities left him drained while others left him energized—even when the people involved were great. That contrast revealed something important: Energy can be a subtle but reliable indicator of the work you're meant to do. Carl suggests paying closer attention to what gives you energy and what quietly takes it away, and using that awareness as a guide—especially when building a “stop doing list.” Over time, tuning into this signal may help clarify what truly belongs in your work and 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, Carl asks a deceptively simple question: Are you waiting for information, or are you waiting for permission? Reflecting on conversations he had after moving to New Zealand, Carl explores how often people say they can't make a big life decision because they lack money, timing, or certainty—when the real barrier may be a fear of acting in uncertainty. In complex systems like careers, markets, and family life, clarity rarely comes before the move. Carl invites us to examine whether we're truly missing information or quietly waiting for reassurance that everything will be okay—and reminds us that emotional data deserves a place in the decision-making process.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 the tension between what's rational on paper and what's workable in real life. Spreadsheets say to invest lump sums immediately, keep low-interest debt, and avoid holding excess cash. The math is often right. But the spreadsheet doesn't model loss aversion, regret, sleep, or the behavioral breaking point of being human. Strategies like dollar-cost averaging or paying off a mortgage may be mathematically suboptimal but psychologically stabilizing. Carl argues that these choices are often a form of emotional insurance, not mistakes. The key is simply to name them honestly: Sometimes the smartest line in the spreadsheet is the human factor.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 “uncertainty drag”—the hidden friction that uncertainty adds to our decisions and momentum. Like cash drag in investing, uncertainty drag slows progress as projects get delayed, hiring pauses, capital sits idle, and life decisions get postponed. Nothing catastrophic has happened, but things start to feel stuck. Carl explores how raising the bar for certainty can quietly cost us missed opportunities, experiences, and creative progress. The key question becomes: Where are you demanding more certainty than the system can actually provide—and what small, safe-to-fail experiments could help you 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, Carl explores the growing trend of “wait-and-see mode”—the instinct to pause decisions when uncertainty feels high. While it can seem prudent, Carl points out that waiting is still a decision, and it always carries a cost. The key question isn't whether waiting is right or wrong, but what exactly you're waiting for. By defining the catalyst that would move you out of “wait-and-see mode,” you can turn passive hesitation into an intentional strategy. Otherwise, what feels like patience may simply be waiting for comfort rather than clarity.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 thought that came to him on a morning walk in the mountains: Artificial intelligence isn't a threat, it's a reminder. As tools become faster at summarizing, analyzing, and generating answers, the truly scarce resource becomes something machines cannot replicate—human wisdom. Carl reflects on wisdom as the ability to apply knowledge with judgment, perspective, and moral clarity, and suggests that the rise of AI only highlights how valuable that capacity is. For him, cultivating wisdom happens through long walks with nothing in his ears, more silence, and deep conversations—the kinds of practices that create space for discernment, meaning, and the slow growth of understanding.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 the "How to Plan" series, Carl explores what may be the most important principle of all: preparing to be wrong. Real planning, he argues, isn't about being precisely correct today. It's about becoming less wrong tomorrow. Once we draw the line, the work shifts to running small experiments and actively seeking disconfirming evidence instead of defending outdated maps. New information, even when it's uncomfortable, feeds back into purpose, goals, and current reality, helping us adjust course. Planning becomes a living process, not a static prediction. The beauty is in embracing wrongness as the path to getting closer to what's true.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 returns to his “How to Plan” series and introduces the next step: drawing the line. After clarifying purpose, defining goals, and understanding current reality, it's time to build the plan—the map from here to there. But Carl reminds us of a crucial paradox: Every plan is wrong; the only question is how. Like a flight plan or a backcountry route, the value isn't in perfect prediction—it's in creating a baseline to adjust from. A plan is a model of an expected future reality, something to hold with strong conviction and loose hands. Because the real magic often lives in what doesn't go according to plan.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 reflects on the stories we instantly tell about money—especially when it comes to visible signs of consumption, like homes and cars. A passing glance at someone's lifestyle can trigger assumptions about success, character, or values, even though we rarely know the real story behind the purchase. Carl turns the lens on himself, noticing how quickly narrative creeps in, and asks a deeper question: What stories does our own spending tell, and how often are we projecting incomplete stories onto others? It's a thoughtful exploration of money, identity, and the invisible narratives we carry around every day.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 one of the hardest kinds of decisions: choosing between two genuinely good options. When every meaningful "yes" contains a painful "no," the tension isn't about right versus wrong—it's about trade-offs. Sharing a simple but piercing question from Christy Raines—“Who do I want to disappoint?”—Carl unpacks how every decision has a shadow, whether it's a client, a family member, or your future self. The choice may not become easier, but it often becomes clearer. Because the real work isn't avoiding tradeoffs—it's deciding, intentionally, which ones you're willing to carry.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 walks through the second step of purpose-based planning: turning purpose into goals. Rather than asking clients to name goals out of thin air, he explains how goals naturally grow out of conversations about what matters, giving people permission to relax, guess, and explore without false precision. Carl shows how to frame, prioritize, and rank goals based on what's truly at stake for each client, reminding us that goals are provisional, flexible, and meant to clarify direction, not lock anyone into a rigid plan.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/