Behavior Gap Radio

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 wraps up his reflections on strategy versus tactics and names the trap he sees everywhere: tactic substitution. It’s easy to copy someone’s tools, workflows, or visible habits without understanding the deeper worldview, positioning, and identity beneath their success. Tactics are concrete, measurable, and easy to sell. Strategy is abstract, slow, and uncomfortable. Drawing on ideas from Seth Godin, David C. Baker, James Clear, Cal Newport, and Steven Pressfield, Carl explores how buying tools can become a way to avoid the harder questions of identity and purpose. At the heart of it all is a simple tension: Do you want another tactic, or are you willing to confront who your work is for and what it actually does?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 hard but essential distinction: strategy precedes tactics. Drawing on ideas from Seth Godin, he argues that strategy answers two simple but demanding questions: "Who is it for?" and "What does it do?" Tactics are merely the downstream execution. Without clarity on strategy, optimizing headlines, funnels, and email cadence only amplifies noise. Through the familiar “Stephen King’s pen” story, Carl points out how focusing on tools can become a place to hide from the real work. The map isn’t the problem. The real challenge is having the courage to draw your own.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 the market for feeling productive is far larger than the market for actually doing the work. Reflecting on years of watching people chase tactics, hacks, and maps, he points to Seth Godin as a consistent voice who refuses to confuse tools with craft. Morning routines, specific pens, productivity systems—these are downstream artifacts, not the cause of meaningful work. The real shift isn’t finding the perfect map; it’s cultivating the courage to draw your own.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 the essay “Tool Shaped Objects”: The market for feeling productive is far larger than the market for actually being productive. From webinars about writing to habit books, templates, and optimization systems, it’s often easier to buy preparation than to do the work itself. Why? Because preparation feels like progress without exposing us to risk, rejection, or uncertainty. Doing the real thing is vulnerable. Carl turns the lens on himself—and on us—with a simple but uncomfortable question: Are you in the market for feeling productive or are you ready to actually be productive?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 walks through step three: current reality. After starting with purpose and letting goals grow from that foundation, it’s finally time to ask, “Where are you today?” But Carl reminds us that even something as seemingly objective as a balance sheet is filled with stories, tradeoffs, and emotion. From assets and liabilities to income and cash flow—and even the invisible, off-balance-sheet values like simplicity, community, or time at home—understanding current reality is about more than numbers. It’s about seeing clearly where you stand before building the path forward.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/ 

In this episode, Carl revisits the idea of risk tolerance and challenges the assumption that it’s a stable personality trait that can be measured with a score. Drawing on research from Paul Slovic and lessons from the mountains, he suggests that when someone says, “I can’t tolerate that kind of risk,” they may not be describing tolerance at all—but fear, lack of trust, loss of control, or an unprocessed memory from 2008. Instead of adjusting portfolios first, Carl argues for adjusting the conversation, separating dread from probability, and getting specific about what actually feels scary—because that’s where the real work begins.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/ 

In this episode, Carl questions one of the foundations of traditional financial planning: risk tolerance. Reflecting on decades of uneasy experience with risk tolerance questionnaires, he asks three simple but powerful questions: Does risk tolerance really exist? Can we measure it? And does it stay constant over time? Then he introduces a provocative idea: when someone appears to have a "high tolerance for risk," maybe it’s not tolerance at all. Maybe it’s an underdeveloped understanding of consequences. Carl invites us to reconsider whether risky behavior reflects personality—or simply a failure to fully grasp what’s at stake.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 the classic risk equation—risk equals probability times consequence—and explains why probability is often the weak link. Drawing on stories from mountain climbing, avalanche education, and investing, he explores how our brains are poorly wired for estimating odds, often substituting confidence and vivid stories for statistical reality. Instead of obsessing over forecasts, Carl suggests shifting focus to consequences: If I’m wrong, what happens? From terrain choice in the backcountry to portfolio design in uncertain markets, he makes the case that humility, a margin of safety, and resilience in the face of uncertainty are far more reliable than precise probability predictions.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 about a surgeon retraining in his 50s to use new robotic tools—and uses it to explore a bigger idea: it’s easy to get distracted by tools and forget the job to be done. The goal isn’t the hammer, the robot, or the latest technology. The goal is the outcome. Whether that’s better patient results, clearer advice, or kindness and connection at scale, tools only matter if they serve the purpose. Instead of feeling threatened by new technology, Carl suggests getting clearer about what you’re actually trying to do in the world—and then choosing the tools, old or new, that help you do that better.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 series on the craft of asking better questions in financial planning, focusing on how to shift the frame—not just the content—of a conversation. Rather than refining answers, he encourages planners to question the assumptions underneath them with prompts like, “What problem are we trying to solve?” or “If this plan is a hypothesis, what are we actually testing?” In a probability-based environment where outcomes are uncertain, Carl argues that the real work is improving the decision-making process itself. Good questions don’t just optimize answers—they change how we think about the game.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 idea for better money conversations: ask questions that create a productive pause. Drawing on facilitation research, he explains that the quality of attention in the room matters more than the cleverness of the question—and that real insight emerges when people feel safe enough to think, not pressured to perform. Through short, disarming prompts like “What feels unsettled here?” or “What are we pretending not to notice?” Carl shows how well-placed silence and genuine curiosity can unlock honesty, deepen trust, and lead to more meaningful financial planning.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/ 

In this episode, Carl makes the case that great planning doesn’t happen in spreadsheets—it happens in conversation. He explores a simple but powerful shift in how we ask questions: trading abstract opinions for concrete memories. Instead of asking, “What do you think?” try, “Can you remember a specific time when…?” Because when we ask for memories, we move past polished narratives and identities and get closer to lived experience—the emotional data that actually drives financial decisions and risk behavior. From market fear to retirement numbers to childhood money stories, Carl shows how better questions lead to deeper clarity, stronger alignment, and more meaningful planning conversations.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 steps outside the planning series to share a reflection that’s been on his mind: Money may be the loudest form of capital, but it’s the least interesting—and often the least dangerous when misused. Exploring the four sources of capital—money, time, energy, and attention—he argues that while we obsess over what’s easiest to count, the real long-term damage comes from quietly misallocating the forms of capital we can never earn back. With a simple thought experiment, Carl invites us to reconsider what truly compounds over a lifetime and where our attention is actually going.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 special Sunday edition, Carl reflects on a quote from Debbie Millman: “Money is never about money. Instead, it's an intellectual exchange for something you believe will make you feel better." Carl explores how easy it is to quietly give money jobs it cannot do—like providing lasting security, love, pride, or a sense of enough. While money can create options and comfort, it can’t deliver infinite satisfaction. The invitation for the weekend is simple: Make a list of the jobs you’ve given money, then notice which ones it can actually perform and which ones it never will.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 walks through the first step of purpose-based planning: uncovering what truly matters before building any plan. He describes purpose as something to be rediscovered through careful, human conversation rather than invented, and shares practical ways to ask better questions, listen for emotional clues, and turn values into a clear Statement of Financial Purpose. The goal is simple but foundational. Start with "why," so every future decision has something solid to align to when the noise, fear, or complexity shows up.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/ 

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