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

In this episode, Carl continues his exploration of the idea that feelings are data by introducing the concept of “affect as information.” Drawing from established research, he examines how we constantly use our emotions as a source of information when making decisions—often without realizing it. Rather than treating feelings as something separate from rational thinking, Carl explores how they may be an essential part of how humans navigate uncertainty, assess situations, and make sense of the world, especially when it comes to money and the choices that matter most.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 lays out the first claim in a growing body of work he's developing around a simple but provocative idea: Feelings are data. Not just emotions to be managed or ignored, but early-stage information that often arrives before words, analysis, or conscious thought. Carl explores how feelings can signal what matters, what feels safe or threatening, and where our values are being honored or violated—making the case that they deserve a place alongside facts and spreadsheets in the way we make decisions about money and 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, Carl begins a deeper exploration of a simple but often overlooked idea: Feelings are data. Challenging the common assumption that emotions are somehow less valuable than spreadsheets, analysis, or technical expertise, he starts building a case that our feelings deserve a legitimate place in decision-making. Drawing from research, experience, and years of conversations around money, Carl explores what might change if we treated emotions not as distractions from the truth, but as information worth paying attention 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 explores a provocative idea: What if financial planning is less about thinking and knowing, and more about feeling? Drawing on conversations from retreats and The Collective, he reflects on the possibility that our bodies often recognize truth before our minds can explain it. Whether it's fear, excitement, resistance, or alignment, Carl argues that paying attention to what we feel may be one of the most overlooked skills in helping people build a healthier relationship with money and make better decisions about 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 reflects on what people are really looking for when facing an uncertain future. More often than not, it's not a perfect plan, a case study, or a detailed roadmap. It's a companion—someone willing to walk alongside them through uncertainty with wisdom, presence, and care. Carl explores the limits of prediction, the reality of not knowing what comes next, and why the most valuable role an advisor, friend, or partner can play is not providing certainty, but offering steady companionship on the journey.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 a simple sketch that captures a powerful idea about personal growth: the relationship between stimulus, response, and awareness. Early on, our reactions can feel automatic, with no space between what happens and how we respond. But over time, awareness begins to show up—first after the fact, then closer and closer to the moment itself. Carl reflects on how real change often starts not by controlling our reactions, but by simply noticing them, and how cultivating that awareness can gradually create more space, choice, and freedom in our 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 explores the idea of public work as a spiritual practice and reflects on the uncomfortable emotions that surface when we compare ourselves to others. After seeing someone launch a project similar to one he'd been thinking about for years, Carl examines his own reactions: jealousy, insecurity, ego, and the stories we quickly tell ourselves. He shares why building a business, making art, and doing work in public can become powerful opportunities for self-awareness, growth, and refinement, if we're willing to pay attention to what gets stirred up along the way.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 difficult and deeply personal work of unwinding the stories we've inherited about success, work, relationships, achievement, and identity. He explores how many of our financial decisions are shaped by assumptions we never consciously chose, and why real financial planning often means slowly peeling back those layers to discover what actually matters to us. It's a thoughtful conversation about alignment, self-awareness, and the lifelong process of becoming more fully ourselves.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 rare moments in life when an opportunity feels so deeply aligned that the question becomes, “How could I possibly say no to this?” Using the example of getting into a dream school like Juilliard, he reflects on regret minimization, the difference between making the “right” decision and making a decision right, and the mysterious way life sometimes rearranges itself after we commit to something meaningful. It's a thoughtful conversation about risk, dreams, uncertainty, and the courage to say yes.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 questions that comes with making meaningful life decisions: How do you tell the difference between anxiety and insight? Reflecting on career changes, relationships, financial decisions, and the messy middle of personal growth, he examines the different textures of fear, urgency, clarity, and alignment. It's a thoughtful exploration of slowing down, listening carefully, and learning to recognize whether we're spinning in circles or moving toward something 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 reflects on a quote from Howard Thurman that has shaped his thinking for years: “Don't ask what the world needs. Ask what makes you come alive and go do it.” He explores the tension between building a life around demand versus building one around aliveness, and the complicated reality that often follows when what makes us come alive doesn't fit neatly into stability, responsibility, or conventional success. It's a thoughtful exploration of ambition, freedom, roots, creativity, and the difficult question of what it actually means to “go do 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 a recent conversation with Michael Kitces about fear-based selling and the surprising world of “disturb tracks” designed to create urgency and anxiety. Carl explores why tactics built on fear, complexity, and pressure may “work” in the short term, but ultimately erode trust and connection. It's a thoughtful conversation about values-based selling, long-term relationships, and the kind of work Carl actually wants to do in the world.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 it feels like to live in a world where the list of things that matter seems impossibly large, while the list of things we can actually control feels painfully small. Revisiting one of his earliest sketches, he explores the overlap between concern and agency, and why focusing on the small, local things we can actually do may be one of the most grounding responses to overwhelm, uncertainty, and modern 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, Carl explores what it really means to help people change. Building on yesterday's idea that the market for feeling something is much larger than the market for becoming it, he reflects on the delicate work of helping clients move from awareness to identity to action. It's a thoughtful look at financial advice, behavior change, and the quiet, human work of helping someone become the kind of person they want to be.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 surprisingly large gap between feeling productive, being seen as productive, and actually doing meaningful work. He reflects on how easy it is to confuse organizing, planning, researching, or publicly announcing our intentions with the vulnerable act of creating something real. It's a thoughtful look at identity, risk, and the subtle ways we avoid uncertainty while still convincing ourselves we're making progress.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 moment of clarity after being told he wasn't a fit for a market-focused podcast—and why that turned out to be exactly right. He explores the important difference between markets and investing, and why chasing daily commentary isn't the same as doing the real work of aligning money with a meaningful life. It's a reflection on knowing what game you're playing, letting go of noise, and focusing on the kind of thinking that actually helps people make better decisions over 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 reflects on a powerful idea inspired by Martin Luther King Jr.: The arc of the moral universe bends toward justice—but what about our own personal arc? He explores how money and power can quietly influence our decisions, sometimes pulling us away from what we say we believe. Rather than judging others, Carl turns the lens inward, asking where we might bend our own standards under pressure—and how to notice those moments before they shape who we become.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 surprising personal story about being “fired” from his own financial planning meetings—and why he was secretly thrilled about it. That experience leads to a deeper question: What if the so-called “disengaged” partner isn't a problem to fix, but simply someone who's playing to their strengths? Carl challenges a common assumption in financial planning and explores a different approach—one rooted in trust, clear communication, and letting people focus on what they're actually good at.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 deeper purpose behind his work and a simple realization that keeps guiding him: Money is the entry point, but kindness is the point. While conversations often start with money, they quickly reveal what really matters—how we spend our time, energy, and attention, and what we want to build in the world. Carl shares why he continues to use money as the doorway, even though the real work has always been about love, connection, and being human.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 personal story about a decision to step away from social media noise and focus on one-to-one connection—and the surprising long-term impact it's had. What started as replying thoughtfully to emails turned into years of meaningful moments with people who never forgot being seen and heard. Carl reflects on a simple idea: Kindness compounds. Not in an abstract way, but in real relationships, trust, and unexpected returns over time—while the opposite carries a cost that shows up when you least expect 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 explores the deeper meaning of compounding—not just as a financial concept, but as a universal life principle. Drawing from wisdom across cultures and centuries, he reflects on how the most valuable things in life—health, relationships, skills, and creativity—are built slowly through consistent, repeated effort. Instead of chasing shortcuts, Carl makes the case for investing your time, energy, and attention into things that grow over time and letting them compound into something meaningful.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 story from a trip to Chamonix that challenged his assumptions about money, value, and how the world works. After a failed attempt to order eggs outside of breakfast hours, he's reminded that not everything is about paying more to get what you want—sometimes it's about craft, culture, and a completely different way of seeing things. Carl reflects on how travel and new environments can expand our perspective on money and life, and why those moments of friction might be some of the most valuable experiences we have.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 talks openly about the rise in economic anxiety and what to do when fear shows up. Instead of rushing to answers or hiding behind data, he makes a simple point: It's normal to feel scared when things are uncertain. The real first step isn't solving the problem, it's creating space to talk about it honestly—with empathy, not dismissal. Whether you're the one feeling the fear or the one others turn to for guidance, Carl explores how making room for that emotion can lead to better, more grounded decisions about what to do next.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 elusive idea inspired by Zen teaching: If you can't find “enough” where you are, where do you expect to find it? He explores how easily we fall into the trap of believing satisfaction is just one step ahead—a bigger number, a future milestone—only to have the goalposts move again. What if enough isn't something you reach, but something you decide? Carl invites you to sit with that question and consider what might change if you chose, right now, that enough is already here.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 slightly uncomfortable but honest reflection about giving yourself permission to like what you actually like—and to stop pretending otherwise. After declining an invitation to a high-profile economic talk, he explores how often we go along with things simply because we think we're supposed to, from market forecasts to popular books to even skiing. Through a few relatable stories, Carl invites you to notice where you might be following expectations instead of your own interests—and what it might look like to quietly, kindly choose your own path 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 explores a simple idea that keeps proving true: What you think is a flaw might actually be the thing that makes your work resonate. From his hand-drawn sketches to the raw, unedited format of Behavior Gap Radio, he reflects on how the very imperfections he once tried to fix became the most meaningful parts. In a world increasingly optimized to remove friction and polish everything smooth, Carl makes the case for leaning into what's human, messy, and real—and why that may matter now more than ever.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 a surprising idea from Seneca: The real shortcut to riches isn't earning more—it's learning to want less. Drawing from Seneca's writings and his own experience, Carl unpacks why more money rarely leads to a lasting feeling of “enough,” and how our desires quietly expand along with our income. This isn't about rejecting money, but about asking a deeper question: How will you know when you have enough—and what happens if you never decide?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 timeless story often told in Buddhist traditions about a piece of gold mistaken for a “poisonous snake”—and what it reveals about our relationship with money. The story isn't about wealth being good or bad, but about perception: the gap between what something looks like and what it actually does to us. Carl reflects on how easily we chase what glitters without seeing the full consequences, and invites you to slow down long enough to ask a simple but powerful question: Am I seeing what's really there, or just what I want to see?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 tackles the quiet but powerful force of comparison and how it distorts the way we see our own lives. From a conversation about vacations to global data that reframes what “wealth” actually means, he explores how easily we feel behind simply because of who we're standing next to. The real issue isn't what we have—it's who we're comparing ourselves to. Carl invites you to question that comparison set, because changing it might be one of the fastest ways to change how you experience your money and your 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, Carl shares a powerful lesson from Olympic silver medalist Haley Batten about what happens when things don't go your way—and how you respond. Reflecting on her race, where setbacks like a bad start and a flat tire could have ended everything, Carl explores the idea that resilience isn't accidental—it's practiced. From everyday frustrations to high-stakes moments, he invites you to consider how you might train your response, creating space between stimulus and reaction so, when things fall apart, you're ready for 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 shares a powerful idea from Olympic silver medalist Haley Batten: the practice of building “durable confidence.” Instead of relying on vague encouragement like “be confident,” Haley describes intentionally creating evidence you can trust—through journaling, tracking wins, and capturing moments that prove you can do hard things. Carl explores how this kind of grounded confidence becomes especially valuable when things get tough, offering a way to steady yourself when doubt creeps in.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 question: When does money bring us together and when does it pull us apart? Through a memorable exchange at a local farmers market, he explores the difference between transactions that feel human and connected versus those that are optimized, abstract, and distant. Same product, completely different experience. Carl invites you to notice where money becomes a bridge—deepening relationships and community—and where it quietly becomes a barrier, creating distance in the name of convenience.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 dream that left him with a simple but haunting question: Do you understand the power you're dealing with? Reflecting on themes found across philosophy, literature, and spiritual traditions, he explores the idea that money isn't inherently good or bad—but it is powerful, and often more powerful than we admit. Through insights inspired by voices like Austin Kleon, Carl invites you to consider how money can quietly shift from servant to master, and why awareness—not avoidance—may be the most important first step in building a healthier relationship with 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 a provocative idea from Nassim Nicholas Taleb: If you want to break your addiction to the news, try reading it a week late. Using this lens, he explores how little of what we consume is actually useful—and how much of it is just noise dressed up as urgency. From the illusion of staying informed to the subtle pull of constant updates, Carl invites you to question whether the news is helping you make better decisions or simply keeping you distracted.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 powerful metaphor from a friend that reframes how we think about helping in a world that feels overwhelming: Are you manning the lighthouse or in the rescue boat? As our awareness of global problems expands far beyond our ability to act, Carl explores the tension between what we see, what we care about, and what we can actually impact. Both roles matter—guiding others or jumping in to help directly—and the real insight may be recognizing where you are and where you can be most useful right now.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 exploring the idea that there may be a different way to think about money, work, and enough—if we're willing to pause and truly consider it. Through stories like a traveler living on “God's bank account” and the invitation to “consider the lilies of the field,” he reflects on how quickly we dismiss ideas that challenge our assumptions. Instead of rushing to judge, Carl invites you to sit with these questions, let them follow you, and see what they reveal. Sometimes the most valuable insight isn't an answer—it's the willingness to hold a different possibility 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 thought experiment designed to stretch how we think about reality, money, and the assumptions we rarely question. Inspired by ideas from thinkers like Seth Godin, he explores what happens when we stop judging new perspectives and simply consider them—whether it's cultures that see dreams as more real than waking life or worldviews that organize life around something other than work and money. In a world that feels increasingly uncertain, Carl suggests that this openness isn't just interesting—it may be essential. Sometimes the most powerful shift comes not from finding the right answer, but from being willing to see the question differently.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 a deceptively simple question sparked by a conversation about productivity gains: What are you going to do with all that time? Building on ideas from David Allen, Carl reflects on how deleting, automating, and delegating tasks can free up hours—but also creates a new challenge. Instead of filling that time with more work, what if it became space for something more meaningful? From learning new skills to serving others or pursuing long-held dreams, Carl invites you to consider whether reclaimed time is an opportunity not to do more, but to live differently.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 idea he picked up from Tom Sachs: “output before input.” Instead of starting the day by consuming news, email, or social media, Carl explores the value of creating first—writing, thinking, moving, or making something—before letting the outside world in. Whether it's a journal entry, a walk, or a small act of creativity, the practice isn't about perfection or performance. It's about reclaiming attention and starting the day with intention rather than reaction.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 revisits a simple idea and refines it: Instead of focusing on the “next best” or “next smallest” step, what if we just focused on the next step? In a world full of uncertainty, even subtle language can add pressure or create hesitation. Carl explores how shifting to something simpler and more neutral can make action feel lighter, more doable, and less loaded. When the future is unclear, progress doesn't come from perfect planning. It comes from taking the next 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 reflects on how easy it is to hide behind big plans and distant steps instead of taking action on what's right in front of us. Drawing from a recent retreat conversation, he points out how often we get stuck thinking about scale, strategy, or the “hundredth step,” when in reality, progress only comes from the next best step. Planning has its place, but Carl suggests keeping it contained so it doesn't become an excuse. In the end, the only thing that really matters is the step you can take right now.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 phrase that has become surprisingly powerful in difficult moments: “I don't need you to fix this. I just need you to listen.” When things go wrong or emotions run high, the instinct is often to jump straight to solutions. But Carl reflects on how valuable it can be to name what you actually need in the moment. Sometimes clarity and relief come not from advice, but from being heard by someone willing to simply listen.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 how behavior change often depends less on willpower and more on systems. After noticing a recent slip into his “checky check” habit, he explores the idea of building both defensive systems that create space between impulse and action and offensive systems that give you something better to do in that moment. From website blockers to simple alternatives like taking a walk or grabbing a notebook, Carl shares how small structures can help interrupt automatic behavior and make it easier to choose a different response.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 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/