Behavior Gap Radio

In the final episode of the Your Wise Money Friend series, Carl reflects on what it means to hold the mirror gently. A wise money friend helps you see what’s really there—not with blame, but with compassion. It’s that rare mix of an empathetic hug and a well-timed kick in the butt. Because real clarity doesn’t come from shame—it comes from being seen, kindly.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 episode nine of the Your Wise Money Friend series, Carl highlights a defining trait of true support: Instead of rushing to give answers, instead asking better questions. The kinds of questions that invite reflection, spark clarity, and open doors. Because real change doesn’t come from advice, it starts with curiosity.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 of the Your Wise Money Friend series, Carl shares a simple but rare truth: A wise money friend doesn’t have an agenda. They’re not selling, fixing, or convincing. They’re just fully present—genuinely invested in your clarity. Once you’ve felt that kind of presence, you don’t forget it… and you stop settling for anything less.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 the Your Wise Money Friend series with a powerful reminder: A wise money friend believes you are enough—even when you feel like you’ve screwed everything up. They don’t excuse your mistakes, they restore your dignity. Because real change doesn’t come from shame, it comes from remembering who you are.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 episode six of Your Wise Money Friend, Carl explores what it means to honor someone's dreams—big, small, wild, or vague—without judgment. A wise money friend doesn’t roll their eyes or ask, “When are you going to get a real job?” They lean in and say, “Tell me more.” This episode is about learning to hold space for dreams—our own and others’—with curiosity, not criticism. Because dreaming isn’t naive, it’s trust.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 episode five of Your Wise Money Friend, Carl reflects on how true wisdom isn’t pushy. A wise money friend doesn’t rush your process or pressure your decisions—they wait with you. Because they know money decisions are rarely urgent, and often about something much deeper: identity, emotion, and transition.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 episode four of Your Wise Money Friend, Carl shares how a wise money friend helps you pause, not to stop you, but to give you space. Space between the impulse and the action. Space to breathe, to feel, and to choose. Because the point isn’t control—it’s clarity. And that little pause? That’s where alignment 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 episode three of Your Wise Money Friend, Carl reminds us that to a wise money friend, your story is never just about money. They listen between the lines—because behind every financial decision is something deeper: fear, joy, dreams, love. A wise money friend knows it’s all connected, and that’s where the real conversation 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 episode two of Your Wise Money Friend, Carl explores the idea that wisdom isn’t about being right—it’s about being present. A wise money friend won’t hand you a to-do list or correct your choices. Instead, they ask the deeper questions that help you see yourself more clearly. Because the goal isn’t certainty, it’s clarity.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 1,300th episode, Carl kicks off a new series called Your Wise Money Friend. Episode one starts with a simple but powerful idea: A wise money friend doesn’t shame you. They don’t scold, lecture, or judge—they lean in with curiosity. Instead of asking, “Can you afford it?” They ask, “Tell me more.” Because real wisdom isn’t about telling you what to do—it’s about helping you explore why.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 kickoff episode, Carl introduces a new series called Your Wise Money Friend—a collection of short, gentle reflections to help you pause, notice your money patterns, and choose on purpose. No hype. No shame. Just tiny moments of clarity, like a quiet walk with someone who really gets it. Because money isn’t just math, it’s meaning.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/

It’s not about what you spent—it’s about what you felt. In this field episode from Los Angeles, Carl shares a shift in how he thinks about money decisions. Whether it’s a new truck or a fancy coffee, the real question isn’t “Can you afford it?” It’s “What are you hoping this will do for you?” Because every financial choice has a feeling underneath it—and that’s where the real insight 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/

Money isn’t math—it’s practice. In this episode, Carl reframes every financial decision as a chance to get more aligned with who you really are. Not perfect. Just intentional. Not based on someone else’s rules, but rooted in your own values. One choice at a 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/

What if every transaction became a moment of transformation? In this episode, Carl asks what would happen if your values showed up not after you spend, but right before—before the tap, the click, the buy. Because every transaction builds your story, and with one simple pause, you can start writing it on purpose.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 every transaction was a chance to practice your values? In this episode, Carl explores how even the smallest purchases—coffee, groceries, flights—can move from invisible habits to intentional choices. This isn’t about spending less. It’s about spending in alignment, where your money reflects the life you 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/

So much of what we do with money is just autopilot—spend, save, stress, repeat. In this episode, Carl invites us to slow down, feel the pattern, and create space between the trigger and the choice. Because clarity doesn’t live in someone else’s advice—it lives in the feeling between the pattern and the pause.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/

Most people didn’t choose their relationship with money—it was installed by accident. In this short episode, Carl unpacks how our money stories get shaped by childhood, culture, and random moments… and how those unexamined stories still run the show. The good news? You can rewrite the code.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 of Behavior Gap Radio, Carl invites us to imagine a different kind of financial tool—one with a soul. Instead of pushing speed and convenience, what if your banking app paused to ask, “Is this you? Is this what you really want?” Not to judge, but to remind. What if every purchase included a breath—a moment of alignment? Soul and humanity at the center of your spending.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 of Behavior Gap Radio, Carl reframes the idea of “managing money” by asking a bold question: What if the real work isn’t about money at all? What if it’s about rewriting the invisible code running in the background—those old stories, patterns, and emotions driving your decisions? Because let’s be honest… you don’t need another budget. You need better code.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 of Behavior Gap Radio, Carl challenges the endless flood of financial advice by asking a deeper question: What if the problem isn’t that you don’t know what to do, but that you don’t know why you keep doing something else? Real change doesn’t come from another tip or trick—it comes from awareness. From pausing long enough to get underneath the behavior and uncover the belief driving it. That’s the shift, from advice to transformation.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 of Behavior Gap Radio, Carl continues exploring the idea of an emotional operating system for your financial life by asking: What if money is a mirror? A mirror that reflects not just numbers, but your fears, values, upbringing, and culture. Most of us were handed that mirror without ever being taught how to look into it, so we flinch, avoid, or judge. But what if we could learn to look with curiosity instead of shame? That’s the work.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 of Behavior Gap Radio, Carl introduces the idea he’s been wrestling with for nearly two decades: building an emotional operating system for your financial life. Money isn’t just numbers—it’s loaded with meaning, emotion, and identity. From love to shame and status to fear, Carl explores why money keeps us up at night and why asking how it feels might matter more than any spreadsheet ever could.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/

We’ve all heard it: “More money, more problems.” But what if that’s only one way to see it? In this episode, I share a conversation with Rabbi Shira Stutman that helped shift my perspective from viewing money as a burden to seeing it as a tool for possibility. It’s a simple lens change… but it might just change everything, especially if you’ve ever felt guilty, ashamed, or stressed about wanting more.This isn’t just about money.It’s about how we see the world:Problems… or possibilities?

A real email exchange about a home repair gone wrong reveals something deeper: how writing without curiosity—especially when we’re certain we’re right—can turn a simple message into emotional kindling.

If you're frustrated by bottlenecks in your projects, teams, or creative work... look closer. It might be you. In this episode, Carl shares why that's actually good news—and how entrepreneurship, at its best, is a brutal but beautiful path to personal growth.

We all say money can't buy happiness. But deep down, are we hoping it can remove our unhappiness? In this episode, Carl flips the script—and asks what hole we're really trying to fill.

In this episode of Behavior Gap Radio, Carl explores a deceptively simple question: What are you solving for? Whether it’s a mountain bike race, a business idea, or a client conversation, knowing the answer shapes everything—your tools, your preparation, and even your motivation. Carl shares how asking this question (and noticing when the answer changes) has guided his life over the past few years—and how it might do the same for 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 of Behavior Gap Radio, Carl takes us inside a classroom exercise that never fails to surprise him—and might surprise you, too. What’s the first thought or feeling that comes to mind when you see a dollar sign? From dumpster diving as a kid to growing up surrounded by wealth but told “we’re not like them,” Carl shares powerful stories about the money scripts we carry. This episode is an invitation to notice the story, feel the emotion, and maybe even write it down and throw it in the fire.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 of Behavior Gap Radio, Carl shares a quote that hit him like a ton of bricks: “Sooner or later, you’re going to have to give up all hope for a better past.” What does that mean when it comes to money? A lot, actually. Carl dives into how we carry old stories—some ours, some inherited—and how they quietly shape our present. This one’s an invitation to drop the stick, stop rewriting the past, and finally move forward with clarity and compassion.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 of Behavior Gap Radio, Carl shares a sketch—and a story—from his upcoming book, Your Money: Reimagining Wealth Through Simple Sketches, about the power of perspective. Whether it’s a rafting trip gone sideways or a financial challenge that feels overwhelming, sometimes the only way through is up. Carl invites us to rise above the chaos—walk the riverbank, take a breath, talk to a friend—and see the forest, not just the trees.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/

Feeling stuck in a loop? Like every day is just… the same? In this episode, Carl explores what happens when purpose goes missing—and why the smallest spark can change everything. From “bullshit jobs” to freshman soccer referees, this one’s about reclaiming meaning in ordinary moments. You don’t need a big dramatic change. But you do need to decide not to throw in the towel.

What’s more heroic—dying for something or living for it? In this episode of Behavior Gap Radio, Carl explores why it’s often harder (and more meaningful) to show up in the quiet, inconvenient moments than it is to make one grand gesture. From NBA legend John Stockton’s quiet consistency to the daily act of texting a grieving friend, this is a reminder that true courage might just be found in the boring stuff… like doing the dishes.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/

Ever felt that spark when watching someone do something incredible—like you're catching a glimpse of pure passion in action? That feeling isn't random. It's a clue, a breadcrumb, guiding you toward what makes you come alive. In this episode of Behavior Gap Radio, Carl reveals exactly how to decode these moments, uncover your own passion, and turn inspiration into action. Because the world doesn't need more people just getting by—it needs you to Find Your Fire.

Ever grab an electric fence? Carl has—and he says that’s exactly what money conversations can feel like when we don’t expect emotions. In this short episode of Behavior Gap Radio, he shares one simple idea that might change how you talk about money forever: expect feelings. Because money isn’t just numbers… it’s identity, power, fear, and love. When you expect the emotional charge, you won’t be shocked. You’ll be ready.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/

Ever found yourself spiraling into a story before you even know what’s happening? In this episode of Behavior Gap Radio, Carl shares a powerful tool he picked up from a conversation with Henry Shukman: SOS—Sensations Over Stories. When money decisions trigger anxiety, the key isn’t to analyze the story… it’s to drop into the body. Carl unpacks how this simple practice of noticing sensations can shift everything—even if the facts stay the same.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/

When life feels out of control—markets crashing, job uncertainty, financial stress—Carl shares the most reliable response: a flight to simplicity. In this episode of Behavior Gap Radio, he explains how shrinking the problem and focusing on what you can control (even something as small as a single breath) helps restore calm and clarity. It's not about fixing everything. It's about finding solid ground—one square inch at a time—and starting from there.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/

Ever nailed your morning routine only to find yourself doom-scrolling by 2:47 p.m.? In this episode of Behavior Gap Radio, Carl unpacks why we fall off track—even when we know better—and how the real solution isn’t a hack or shortcut… it’s practice. The kind that stings. The kind that invites us to notice, realign, and try again. Again and again. This is about treating creative work—and entrepreneurship—as a spiritual practice. One where the noticing is the win, the fall never ends, and the way forward is simple (but not easy): practice.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 of Behavior Gap Radio, Carl explores the strange magic of urgency and asks a simple question: What are you waiting for? Whether it’s sending that email, raising your fees, or finally writing the thing you’ve been thinking about for years, the time between idea and action doesn’t have to be so long. Carl shares real stories—his own and those of others—to show how much time we waste waiting for the “right” moment. Spoiler: This is your sign. Do the thing.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 of Behavior Gap Radio, Carl shares his most tactical money decision-making tool: the Financial Pause. Forget budgets and spreadsheets—this is about noticing what you're feeling before you act. Carl walks through a four-step process that starts with tuning into your body and ends with making choices from a calm, centered place. It’s simple, powerful, and might just save you from making a financial decision you’ll regret.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 gentle reminder from Behavior Gap Radio, Carl shares what to do when someone comes to you feeling nervous, scared, or uncertain—and thinks action is the answer. Instead of rushing to give advice, Carl encourages us to slow down, lead with empathy, and ask thoughtful questions. Because often, the wisest answers come not from us but from the person sitting across from us—if we’re willing to create the space for them to emerge.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 quiet but powerful episode of Behavior Gap Radio, Carl shares a simple phrase that might just rearrange the furniture in your brain: We live in the feeling of our thinking. Not our circumstances. Not the email. Not the number on the statement. Carl unpacks how noticing our thoughts—not fixing or fighting them—can shift everything. It’s not self-help. It’s not mindset hacks. It’s just awareness. And it changes things.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 of Behavior Gap Radio, Carl comes in hot with a wake-up call about the hidden cost of distractions. He shares shocking stats about how often we're interrupted, how much time we lose to switching tasks, and why most knowledge workers only get two hours of deep work a day—on a good day. But this isn't just finger-pointing. It's Carl confronting his own habits and offering two tiny experiments to help us all reclaim our time: install RescueTime and schedule just two 90-minute distraction-free work blocks. No shame. No blame. Just a deep, empathetic punch in the nose—and a hug.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 takes on the wild, stretchy nature of time—why we can procrastinate for months on a task that only takes minutes. He explores Parkinson’s Law, the mental weight of unfinished tasks, and the surprising productivity gains of adding constraints. With practical tools like the two-minute rule and a three-hour workday experiment, Carl invites you to test the "time illusion" for yourself and reclaim your attention, energy, and calendar.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 powerful framework for navigating creative and financial risk: understanding whether you're playing a luck-based or skill-based game. Drawing on insights from Michael Mauboussin’s book, The Success Equation, Carl explains why sharpening your decision-making process is essential in luck-driven environments—like markets or venture capital—while skill-building is key in more predictable terrain. Knowing the difference just might change the way you approach your next big move.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 personal experiment in breaking free from the “dopamine machine”—those tempting websites and distractions that quietly steal our time. He talks about using defensive measures like locking down access, creating space between stimulus and response, and replacing old habits with more meaningful activities. Along the way, he reflects on meditation, addiction, and the surprising power of simply noticing what we feel instead of trying to suppress 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 what he believes is the greatest risk of all—not failure, but waking up one day and realizing we haven’t been the person we hoped to be. He reflects on daily regrets, the subtle ways distraction can derail our intentions, and why ignoring that quiet sense of misalignment only makes it worse. Most importantly, he offers a gentle reminder: notice the feeling, use it to course-correct, and begin 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 dives into one of his most-quoted ideas: "Risk is what's left over after you think you've thought of everything." He unpacks the concept of residual risk, why it matters in everything from investing to skiing, and how small, safe-to-fail actions can help us navigate uncertainty. Plus, he explores the idea of general resilience—the kind of strength that helps you deal with the unknown unknowns.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 of Behavior Gap Radio, Carl shares a simple but powerful idea: When something feels too scary—whether it’s launching a business, writing a book, or making a big change—just make it smaller. He introduces the concept of microactions: tiny steps that feel almost too small to matter but are exactly what we need to get unstuck and start moving.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 of Behavior Gap Radio, Carl shares a powerful mindset for navigating uncertainty—whether it’s a looming recession or just a vague feeling of unease. Borrowing from his backcountry experience, he introduces the idea of a “flight to simplicity” as a way to reduce exposure to risk. From creative businesses to household budgets, Carl walks through practical ways to make things simpler, delay big decisions, and regain clarity—especially around the margins.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 of Behavior Gap Radio, Carl explores the terrifying beauty of doing work no one asked for. He challenges the conventional path of chasing demand and instead makes a case for following the quiet compulsion to create—especially when it feels scary, uncertain, or totally invalidated. If you’ve ever felt called to make something simply because it lights you up, this one's for 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/