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In this episode, Carl explores the growing trend of “wait-and-see mode”—the instinct to pause decisions when uncertainty feels high. While it can seem prudent, Carl points out that waiting is still a decision, and it always carries a cost. The key question isn’t whether waiting is right or wrong, but what exactly you’re waiting for. By defining the catalyst that would move you out of “wait-and-see mode,” you can turn passive hesitation into an intentional strategy. Otherwise, what feels like patience may simply be waiting for comfort rather than clarity.
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In this episode, Carl shares a thought that came to him on a morning walk in the mountains: Artificial intelligence isn’t a threat, it’s a reminder. As tools become faster at summarizing, analyzing, and generating answers, the truly scarce resource becomes something machines cannot replicate—human wisdom. Carl reflects on wisdom as the ability to apply knowledge with judgment, perspective, and moral clarity, and suggests that the rise of AI only highlights how valuable that capacity is. For him, cultivating wisdom happens through long walks with nothing in his ears, more silence, and deep conversations—the kinds of practices that create space for discernment, meaning, and the slow growth of understanding.
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In this episode of the "How to Plan" series, Carl explores what may be the most important principle of all: preparing to be wrong. Real planning, he argues, isn’t about being precisely correct today. It’s about becoming less wrong tomorrow. Once we draw the line, the work shifts to running small experiments and actively seeking disconfirming evidence instead of defending outdated maps. New information, even when it’s uncomfortable, feeds back into purpose, goals, and current reality, helping us adjust course. Planning becomes a living process, not a static prediction. The beauty is in embracing wrongness as the path to getting closer to what’s 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 returns to his “How to Plan” series and introduces the next step: drawing the line. After clarifying purpose, defining goals, and understanding current reality, it’s time to build the plan—the map from here to there. But Carl reminds us of a crucial paradox: Every plan is wrong; the only question is how. Like a flight plan or a backcountry route, the value isn’t in perfect prediction—it’s in creating a baseline to adjust from. A plan is a model of an expected future reality, something to hold with strong conviction and loose hands. Because the real magic often lives in what doesn’t go according to 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 reflects on a line from William Wordsworth written in 1802: “Getting and spending, we lay waste our powers.” Carl explores how Wordsworth was already warning about the danger of a culture obsessed with acquisition and consumption. The real loss, he suggests, isn’t moral or financial. It’s the quiet erosion of our attention, imagination, and sense of wonder. Carl invites listeners to consider a deeper risk around money: not losing it, but losing the parts of ourselves that money can never buy.
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 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.
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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.
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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/
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