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

In this episode, Carl explores the value of intentionally putting ourselves in situations where we don't quite know what to do next. Through stories from the mountains, travel, and unexpected career changes, he considers how small, safe encounters with uncertainty can build something far more useful than having all the answers: trust in our ability to figure things out.Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com 

In this short episode, Carl explores a deceptively simple question: What if more isn't always the answer?Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this short episode, Carl explores the difference between understanding risk in theory and actually experiencing it. What changes when risk stops being an idea and suddenly becomes real?Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/ 

In this short episode, Carl explores what it might actually mean to live a meaningful life. What if it's less about finding one big answer and more about what we choose to do with the resources 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 short episode, Carl explores the tension between keeping your options open and actually choosing a life. When does flexibility stop being freedom and start getting in 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 short episode, Carl shares his favorite part of real financial planning. Before the numbers and plans, there's a simpler question: What is all this money for?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 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 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/