Podcast appearances and mentions of Carl Richards

In the 197th episode of Kitces and Carl, Michael Kitces and client communication expert Carl Richards discuss how to go about figuring out what's important to clients (and how to help them figure it out for themselves). For full show notes, see kitces.com and thesocietyofadvice.com.

We all know the importance of having a good financial plan in place. But…are we all talking about the same thing? What *is* a financial plan, and how do we know if ours is good or not?  Looking for a financial planner?  → PlanWithJesse.com Jesse explores what financial planning actually is, why it extends far beyond investing, and how to know whether your financial plan is truly working. He begins by defining financial planning as a comprehensive process that aligns every aspect of your financial life—including cash flow, taxes, investments, insurance, retirement, and estate planning—around your unique goals and values. Jesse explains why clear goals, a structured planning process, and an integrated long-term strategy are the foundation of every effective financial plan, illustrating how changes in one area of life inevitably ripple through every other financial decision. Drawing on ideas from the CFP Board, Carl Richards, and George Kinder, he emphasizes that financial planning is not a one-time event but an ongoing, dynamic process that evolves as your goals, finances, and life circumstances change. He concludes by outlining 22 practical signs that a financial plan is succeeding, arguing that true success is measured not only by growing wealth but also by greater clarity, confidence, better decision-making, reduced financial anxiety, stronger family alignment, and the freedom to make important life decisions with purpose rather than emotion. Key Takeaways: • Financial planning is about helping you achieve life goals through coordinated financial decisions, not simply managing investments. • Good financial planning integrates investments, taxes, insurance, cash flow, retirement, and estate planning into one cohesive strategy. • Following a structured planning process leads to better decisions than jumping straight to recommendations. • Couples who share financial goals tend to make better long-term decisions together. • The best financial plans reduce the amount of time and energy you spend worrying about money. • The ultimate measure of financial planning success is greater confidence, clarity, and permission to live your life according to your values—not simply having a larger portfolio. Key Timestamps: (01:24) – What Is Financial Planning? (04:29) – Financial Goals (06:09) – Different Facets of a Good Financial Plan (07:34) – Follow a Process (10:19) – Creating a Strategy (15:11) – Bringing Everything Together (18:18) – Three Questions for Life Planning (22:58) – 22 Ways to Know the Plan Is Working Key Topics Discussed: The Best Interest, Jesse Cramer, Wealth Management Rochester NY, Financial Planning for Families, Fiduciary Financial Advisor, Comprehensive Financial Planning, Retirement Planning Advice, Tax-Efficient Investing, Risk Management for Investors, Generational Wealth Transfer Planning, Financial Strategies for High Earners, Personal Finance for Entrepreneurs, Behavioral Finance Insights, Asset Allocation Strategies, Advanced Estate Planning Techniques Mentions: https://bestinterest.blog/e83/  More of The Best Interest: Check out the Best Interest Blog at https://bestinterest.blog/ Contact me at jesse@bestinterest.blog Need a financial planner?  → PlanWithJesse.com  The Best Interest Podcast is a personal podcast meant for education and entertainment. It should not be taken as financial advice, and is not prescriptive of your financial situation.

In the 196th episode of Kitces and Carl, Michael Kitces and client communication expert Carl Richards discuss the role of "gut feelings" and intuition in decision-making after the data has been fully analyzed. For full show notes, see kitces.com and thesocietyofadvice.com.

In this episode, Carl explores a simple question that can quietly change the direction of a day: What if we just go? Reflecting on a spontaneous trip to the river, he considers how often reluctance, uncertainty, or the desire for comfort keep us from experiences that end up being deeply worthwhile. Rather than guaranteeing a particular outcome, choosing to go simply guarantees participation, and Carl suggests that many of life's best moments are waiting just beyond the point where we almost decide to stay home.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 challenging idea from Aldous Huxley: “Change is only possible through movement.” Instead of waiting until we're certain about the outcome, he argues that clarity comes from taking small steps, gathering new information, and adjusting along the way. Carl explores why progress in complex situations isn't about having the perfect plan, but about having the courage to move before you know exactly where the path will lead.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 happens when you find yourself in over your head. After a humbling day on the trail, he realized the most valuable lesson wasn't failure, but the reminder that there was still so much to learn. Carl explores why taking on projects that feel just beyond your current abilities can spark growth, humility, and curiosity—and why becoming the kind of person who can do the thing often matters more than simply accomplishing 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 a question we all face eventually: How do you know when it's time to quit, and when it's time to keep going? Reflecting on a day when he wanted to walk away from several meaningful projects, he shares how moments of discouragement can reveal what's truly worth our time, energy, and attention. Rather than treating the urge to quit as failure, Carl suggests it may be an invitation to pause, regain clarity, and decide whether you're being called to let go or simply take 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 the 195th episode of Kitces and Carl, Michael Kitces and client communication expert Carl Richards discuss how to strike the right balance between proactive and reactive client communication. For full show notes, see kitces.com and thesocietyofadvice.com.

In this episode, Carl reflects on a simple idea with profound implications: What if money's natural state is movement rather than accumulation? From paying bills to giving generously, he explores the possibility that money is meant to flow through our lives, creating value and connection along the way. Instead of seeing every dollar as something to hold onto, Carl invites us to consider how our relationship with money might change if we viewed it as part of a continuous cycle of exchange.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 an often-overlooked truth about inheritance: We don't just inherit money, we inherit the stories that come with it. Those stories can shape how we feel about wealth, influence our financial decisions, and even carry unresolved questions about family, sacrifice, identity, and love. Whether you've inherited money yourself or work with people who have, Carl offers a simple invitation to look beyond the dollars and become curious about the story they're carrying, too.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 moments when a conversation about money quietly becomes a conversation about what really matters. Inspired by a discussion with Rabbi Shira Stutman, he explores how values like safety, freedom, love, and justice often emerge beneath financial decisions—and why learning to recognize these “crunchy bits” is one of the most important skills we can develop. It's a thoughtful invitation to practice noticing the subtle emotional shifts that signal when the real conversation has finally begun.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 paradoxical question: What if your goal is to have no goals? Reflecting on conversations with people who have spent years optimizing every part of their lives, he wonders what it would mean to stop striving and simply become more present. Rather than seeing this as giving up, Carl suggests it may be one of the bravest goals of all—a shift away from constant achievement and toward the far more challenging work of exploring your inner landscape with curiosity, compassion, and openness.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 a simple practice that can transform your relationship with money—one spending decision at a time. Since spending is our most frequent interaction with money, he suggests treating it as a daily practice rather than something to do on autopilot. For the next 30 days, every time you spend money, pause for three seconds and simply notice what happened, approaching it with curiosity instead of judgment. Carl explains why this small habit of awareness can quietly reshape not only how you spend, but how you relate to money itself.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 remarkable insight from movement teacher Ido Portal: Truly great teachers don't simply provide answers—they create the conditions for curiosity, exploration, and discovery, especially where clear answers don't yet exist. Carl explores what this means not only for teaching, but for parenting, friendships, leadership, financial advice, and any relationship where our role is to help others uncover what matters most for themselves.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 one of his favorite questions from Mary Oliver: “Tell me, what is it you plan to do with your one wild and precious life?” Focusing on the words plan and wild, he explores the creative tension between thoughtful planning and embracing life's unpredictable nature. Rather than choosing one over the other, Carl suggests that a meaningful life requires both—a plan that gives direction and enough openness to let the most beautiful, unexpected moments emerge 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 milestone 1,500th episode, Carl reflects on the quiet power of showing up consistently. Looking back on years of recording Behavior Gap Radio, tending a garden, and watching small efforts compound over time, he shares why the most meaningful changes in life rarely come from dramatic breakthroughs. Instead, they grow through steady, daily practice. It's a celebration of patience, compounding, and the reminder that the things most worth building are often the ones that can't be rushed or hacked.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 question that can completely change the way we think about spending money, time, energy, and attention: What value am I actually trying to express? Through stories about beach houses, family gatherings, friendships, and everyday decisions, he shows how we often mistake the object for the purpose. Once we identify the deeper value we're trying to honor, new possibilities emerge—often simpler, more meaningful, and more aligned with the life we actually want to live.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 choosing a “forcing function”—a meaningful project or experience that asks something of you and reveals what really matters. Inspired by a friend taking a three-week sabbatical to write, he reflects on the surprising resistance that can arise when we give ourselves permission to pursue something that feels deeply important. Whether it's a garden, a road trip, an art class, or a long walk, Carl suggests that the value isn't in the activity itself but in the questions it invites us to ask about our priorities, our stories, and the life we truly want to build.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 the 194th episode of Kitces and Carl, Michael Kitces and client communication expert Carl Richards discuss the ongoing debate surrounding fear-based marketing tactics. For full show notes, see kitces.com and thesocietyofadvice.com.

In this special anniversary episode, Carl reflects on 31 years of marriage and the quiet power of compounding kindness. Looking back over more than 11,000 days together, he celebrates not perfection, but the daily practice of forgiveness, patience, and choosing kindness again and again. It's a heartfelt reminder that the most meaningful investments aren't passive—they're made one small act at a time, and over the years, they grow into something far greater than we could have imagined.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 most honest questions we can ask ourselves: What if I don't know what I want? Building on the idea of choosing a meaningful project as a tool for transformation, he reflects on why discovering what truly matters is so difficult in a world shaped by borrowed desires and cultural expectations. Rather than searching for a perfect answer, Carl suggests gently clearing away inherited ambitions and letting real experiences ask deeper questions about what energizes us, what we're willing to rearrange our lives around, and what makes us feel more alive—not just more impressive.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 invites you to slow down and simply notice what surfaced after yesterday's reflection on choosing a meaningful project. Whether it was excitement, frustration, shame, curiosity, or nothing at all, he encourages you to resist the urge to fix it or act on it immediately. Instead, treat it as information. With gentle curiosity, Carl explores the practice of paying attention to your feelings, giving yourself permission to wonder again, and taking the first small step toward rediscovering what truly matters.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 question at the heart of both meaningful living and real financial planning: What's worth living for? He reflects on how most of us have been trained to ask practical questions like, “What can I afford?” instead of deeper ones like, “What makes me come alive?” Rather than waiting for perfect clarity, Carl suggests choosing a meaningful project—not because the project is the goal, but because it becomes a tool for transformation, revealing what we truly value and what we're willing to reorganize our lives around.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 question inspired by a conversation with Dan Sullivan: What if your future was bigger than your past? As many people begin shrinking their lives with age, Carl wonders what it would look like to keep growing instead—not by doing more, but by taking on meaningful projects that continue to transform us. It's a thoughtful meditation on adventure, rest, purpose, and why the most important investment we make may be in a future that still excites 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 powerful lesson from a conversation with leadership expert Jennifer Garvey Berger about the importance of questioning our assumptions. What sounds like a simple client goal—“I just want a stable future”—turns out to contain layers of meaning that we can easily overlook if we assume we already understand. Carl reflects on the discipline of deep curiosity, the art of asking better questions, and Jennifer's humbling reminder that she goes to such lengths because she has learned she is “almost always wrong” about her first assumptions.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 quickly we build stories from incomplete information—and how often those stories turn out to be wrong. Through personal experiences involving family, clients, and everyday conversations, he explores the assumptions we make, the certainty we attach to them, and the humility required to question our own narratives. It's a thoughtful reminder that there are always multiple sides to a story, and that staying curious about our assumptions may be one of the most valuable practices we can develop.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 one simple but surprisingly powerful question from a recent retreat: What's one thing you've changed your mind about? As stories unfold around the table, he explores the remarkable human capacity to revise long-held beliefs, let go of old stories, and see the world differently. Through a personal example of discovering he'd misunderstood part of his wife's relationship with money for decades, Carl reminds us that changing our minds isn't a weakness—it may be one of the clearest signs that we're still learning.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 idea of obsession—not as something unhealthy, but as the kind of deep fascination that brings a person fully alive. Drawing on wisdom from Howard Thurman and a Zen teaching about living “as though a fire were raging in your hair,” he explores what it means to rediscover the interests, questions, and pursuits that quietly call to us. It's an invitation to notice what captures your attention, rekindle what once lit you up, and make a little room for the thing that won't stop asking to be noticed.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 the 193rd episode of Kitces and Carl, Michael Kitces and client communication expert Carl Richards discuss the challenge of motivating clients to take difficult but necessary action toward their goals. For full show notes, see kitces.com and thesocietyofadvice.com.

In this episode, Carl continues his exploration of the idea that feelings are data through a conversation with a friend who approaches decisions very differently—through analysis, spreadsheets, and deep research. What surprised Carl was discovering that even the most analytical decision-makers often pay attention to feelings when something seems “off.” The conversation leads to a simple but powerful distinction: the goal isn't to blindly trust your feelings, but to get curious about them. Feelings may not be conclusions, but they can be valuable clues pointing toward questions worth investigating.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 examines a surprising emotional reaction he had while hearing about an extravagant luxury home—and what that reaction might be trying to tell him. Instead of dismissing the feeling or judging it, he gets curious about it, using it as another example of his growing belief that feelings are data. It's a candid exploration of envy, anger, values, and the stories we tell ourselves about money, wealth, and what a good life looks like.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 his exploration of the idea that feelings are data with a bold claim: When it comes to risk, feelings aren't incidental—they're central. Too often, emotions are treated as noise that gets in the way of good decision-making. Carl argues the opposite. When we're facing uncertainty, fear, excitement, hesitation, and intuition may contain critical information about what matters to us and how we perceive risk. It's a thoughtful look at why understanding our feelings may be just as important as understanding the numbers.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 paradox he's noticed in some of the most important decisions of his life: While he loves receiving strong, opinionated advice, the people who have helped him most often didn't tell him what to do at all. Instead, they created the space for him to discover his own answer. Reflecting on decision-making, wisdom, and even spiritual maturity, Carl considers the difference between giving answers and helping someone find their path—and why the latter may be far more valuable, even when it feels frustrating in the moment.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 from E. F. Schumacher and the subtle stories we tell ourselves about consumption. Drawing on Schumacher's concept of “Buddhist economics,” he explores how modern culture has gradually transformed consumption from a means to an end—from a tool that serves a meaningful life into a goal in itself. It's a thoughtful invitation to reconsider what consumption is actually for and whether we've mistaken the vehicle for the destination.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 exploration of the idea that feelings are data, taking a closer look at a belief he's carried for years: The body often knows something before the mind can explain it. As he digs into the research behind that intuition, he reflects on the subtle signals we experience physically and what they might reveal about decisions, relationships, and the choices we make around money. It's an exploration of the connection between awareness, intuition, and the possibility that our bodies may be offering information long before our conscious minds catch 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, Carl explores the surprising information hidden inside resistance. Inspired by a conversation at a recent retreat, he reflects on the difference between asking, “What am I going to do next?” and asking, “What am I resisting?” Instead of treating resistance as something to overcome, Carl wonders whether it might be a valuable signal—pointing toward something important, unresolved, or worth exploring. It's a thoughtful look at curiosity, self-awareness, and what our reluctance might be trying to teach 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 the 192nd episode of Kitces and Carl, Michael Kitces and client communication expert Carl Richards discuss how advisors can stay creative without losing sight of the business side of things. For full show notes, see kitces.com and thesocietyofadvice.com.

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 the 191st episode of Kitces and Carl, Michael Kitces and client communication expert Carl Richards discuss how to navigate working with couples when one partner is checked out. For full show notes, see kitces.com and thesocietyofadvice.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/ 

What if the reason your investment decisions feel so hard isn't the market -- it's how you're wired to think about outcomes? Annie Duke spent years as a professional poker player winning over $4 million in tournaments, then devoted the next chapter of her career to understanding why smart people consistently make bad decisions. The answer has nothing to do with intelligence and everything to do with how we confuse results with quality. She brings the full framework down to the basement today.What You'll Walk Away WithWhy certainty is the enemy of good decision making -- and the mindset shift that makes uncertainty feel like an advantage instead of a threatThe Pete Carroll problem: how tying the outcome of a decision to the quality of the decision is quietly wrecking how you evaluate your investmentsWhy being smarter actually makes this bias worse -- and how intelligent people spin data to confirm what they already believe more effectively than anyone elseThe difference between wanting to be right and wanting to be accurate -- and why that single distinction changes everything about how you process new informationHow to hold your beliefs as "works in progress" rather than positions to defend -- and why that opens you up to information that actually improves your decisionsWhy the stock market's short-term volatility is almost never the signal investors treat it as -- and what a 40-year Berkshire Hathaway chart actually tells youThe poker table parallel to long-term investing -- and why you can make all the right moves and still lose, which means a bad outcome never proves a bad decisionWhat the Philly Special play reveals about how we reward boldness only when it works -- and what that tells you about how you judge your own financial choicesA listener question on market-cap weighted index funds -- why the s and p is built the way it is and what you'd actually need to do to weight it differentlyThe best personal finance and business books the crew is reading right now -- including picks from OG that go well beyond the usual recommendationsWhy This Matters NowFor Stackers in their 40s watching a volatile market and second-guessing decisions that were perfectly sound six months ago, this episode is a direct intervention. The temptation to call a good decision bad because the market moved against you -- or to abandon a long-term strategy because of a short-term result -- is exactly the bias Annie Duke has spent her career studying. The framework she brings today doesn't just apply to poker. It applies to every financial decision you'll make for the rest of your life.From the BasementAnnie Duke joins Joe and OG to walk through the decision-making framework behind her book Thinking in Bets -- including the Super Bowl story that reframes how most people evaluate every financial move they've ever made. The headline segment tackles parents spending six figures on kids' extracurriculars and what the trade-off actually looks like for retirement savings. Doug arrives with poker-themed trivia about the all-time tournament earnings leader, gets it mostly right, and declares victory anyway. Whether the basement poker tournament ended in anyone's favor is a matter of some dispute.Resources MentionedThinking in Bets by Annie Duke -- available wherever books are soldAnnie Duke's website and weekly newsletter -- annieduke.comAnnie Duke on Twitter -- @AnniedDukeThe Truth About Money by Ric Edelman -- recommended by JoeSet for Life by Scott Trench -- recommended by JoeBroke Millennial by Erin Lowry -- recommended by JoeHow to Be a Financial Grownup by Bobbi Rebell -- recommended by JoeThe Behavior Gap and The One-Page Financial Plan by Carl Richards -- recommended by OGFooling Some of the People All of the Time by David Einhorn -- recommended by OGBuilt to Sell by John Warrillow -- recommended by OGThe E-Myth by Michael Gerber -- recommended by JoeThe Goal by Eliyahu Goldratt -- recommended by JoeStacking Benjamins Community -- stackingbenjamins.com/basementSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.