Advertise on podcast: Behavior Gap Radio

In this episode, Carl explores a fundamental problem with planning: we’re not very good at knowing what we actually want. Through a conversation with a friend who's tracked his goals for 25 years, Carl reflects on how often our imagined futures change, and why that doesn’t mean we should stop setting goals. It’s an exploration of what goals can give us, even when we’re almost certainly wrong about where we’re headed. 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 kickoff retreat for Cohort 2 of The Collective and what makes this experience so different from traditional professional development. Rather than chasing tactics or business growth, the focus is on discovering what matters and learning to align our money, energy, time, and attention with it. Carl shares what he learned about the power of carefully curated peer groups, skilled facilitators, honest accountability, and creating a place where people feel safe enough to see the gap between what they say matters and how they actually 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 field note, Carl shares an unexpected moment from a recent Society of Advice retreat: A group of people sat quietly on a deck and watched a thunderstorm roll through the Utah mountains. What seemed like a simple pause turned into something far more meaningful, including an uncomfortable confrontation with the urge to always be doing something. Carl reflects on what silence, stillness, and a little wrestling with ourselves might reveal when we finally stop long enough to pay attention. 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 field note, Carl reflects on something that became clear after a recent Society of Advice retreat: The search for a meaningful life can sometimes start to sound like a long list of hard things. But what about the wonder, joy, beauty, love, and sheer amazement of being alive? Carl explores what happens when we make room for it all, including the difficult parts, without forgetting that this whole adventure can be pretty wonderful, 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 short field note, Carl shares two funny moments that left him wondering how often we put up with unnecessary discomfort without realizing there’s a simple fix. From an improperly adjusted rearview mirror to a pair of dirty sunglasses, he explores what happens when we stop struggling with something long enough to question whether it needs to be so difficult 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/

In this episode, Carl shares a story about an innocent email from a client that sent him into a weekend of worry, second-guessing, and unnecessary work. Looking back, he explores how quickly we can turn a simple event into a complicated story about what it means, and how our certainty about that story can cause far more pain than the event 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 short field note from Park City, Carl shares a question that resurfaced during a recent Society of Advice retreat and has followed him around ever since. It’s a simple, generous question that invites us to reconsider what we’re searching for and whether we might be overlooking something important that’s already right in front of 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 short episode, Carl offers a different way to think about artificial intelligence and the questions it raises about our work and our value. As technology changes what’s possible, he invites us to consider one question that may matter more than ever: What’s deeply unique about you? 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 his favorite questions: What are you up to? Whether you’re building something big or still figuring out what that thing might be, he reflects on the power of connecting a larger vision to one small action today. With nothing more than an index card and a little intention, Carl considers how tiny, consistent steps can compound into meaningful progress 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 continues his exploration of being skillfully wrong by asking what it takes to become more comfortable seeing where we fall short. Through a simple daily practice of comparing what we planned to do with what actually happened, he explores how we can learn from our mistakes without beating ourselves up. It’s a reflection on honesty, self-compassion, and the surprisingly difficult practice of accepting reality, learning from it, and starting again. 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 power of silence in our conversations, particularly when we’re trying to help someone discover what matters. Inspired by Thomas Keating and poet David Whyte, he reflects on how uncomfortable we can be with quiet moments and what we might miss when we rush to fill them. It’s an invitation to practice leaving a little more room for silence and notice what becomes possible when we do. Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this episode, Carl challenges the idea that good planning means getting everything right from the start. Drawing on a conversation with a highly skilled business leader navigating uncertainty, he explores what happens when we stop demanding perfect predictions and start treating planning as a process of experimentation, observation, and learning. It’s a different way to think about expertise, uncertainty, and the surprising value of getting things wrong. Want more from Carl? Get the shortest, most impactful weekly email on the web! Sign up for the Weekly Letter from Certified Financial Planner™ and New York Times columnist Carl Richards here: https://behaviorgap.com/

In this field note, Carl imagines what money might say if it could talk, and the conversation takes an interesting turn. What if some of the things we’ve spent our lives asking money to provide are things it was never capable of giving us? Carl explores the complicated relationship between money, security, meaning, and love, and what happens when we start questioning the jobs we’ve given money to do. 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/