Behavior Gap Radio

In this short episode of Behavior Gap Radio, Carl reflects on how easy it is to drift into tracking the wrong metrics—the ones the world cares about, not the ones that actually matter to you. When your attention slips to measures that don’t align with your values, things get messy. The antidote is simple but essential: get clear on what matters, then measure only that. Want more from Carl? Get the...

In this Field Note episode of Behavior Gap Radio, Carl shares a real-time lesson from the chaos of airline travel during his book tour. When you’re navigating a complex adaptive system—whether it’s airports, markets, or major life decisions—the key variable is information. Carl walks through how to gather what you can, when to stop analyzing, and how to take small “micro-actions” designed to gener...

In this episode of Behavior Gap Radio, Carl explores what he calls the discipline of more—or what he sometimes calls the bigger yes. Instead of fighting bad habits through willpower, he suggests crowding them out by filling life with things you love. From moving woodchips under a headlamp to swapping screen time for saunas and books, Carl shares how choosing a “bigger yes” creates space for what m...

In this episode of Behavior Gap Radio, Carl shares a favorite quote from explorer Rick Ridgeway: “The best journeys answer questions we never thought to ask.” He reflects on what that really means—that the purpose of a journey isn’t to chase answers, but to discover better questions along the way. Whether it’s a mountain adventure, a creative pursuit, or the quiet work of introspection, Carl asks:...

In this episode of Behavior Gap Radio, Carl introduces a phrase he’s been searching for: ecological naïveté—the idea that our instincts were perfectly suited for a world that no longer exists. Using examples from nature and investing, he explains why our ancient wiring makes us want to run from market drops and chase safety, even when we know better. The takeaway? You’re not a bad investor—you’re...

In this Field Note episode of Behavior Gap Radio, Carl shares a simple but powerful practice: extreme assumption questioning. From $5 million sailboats to retirement goals and client meetings, he shows how many of our “facts” are really just unexamined beliefs. By treating assumptions like a game—asking, “What if this isn’t true?”—we create the space for new, creative possibilities to emerge. Want...

In this episode of Behavior Gap Radio, Carl explores what he calls “big stupid human tricks”—the kinds of goals that force us to grow into new people. But instead of running a marathon or climbing a mountain, he wonders if the hardest challenge might actually be internal. What if the real adventure is a silent retreat, putting your phone away, or sitting quietly with yourself? Carl reflects on how...

In this episode of Behavior Gap Radio, Carl digs into a simple but unsettling truth: After the fact, randomness always looks like strategy. He unpacks the concept of retrospective coherence—our tendency to turn chaos into neat career stories—and how that illusion feeds “success porn” by hiding the messy role of luck and timing. From startups to financial advice, Carl reminds us that most of what l...

Carl’s back on Behavior Gap Radio with a quick, honest update. He shares what the past week of book launch conversations taught him about defining success, why he briefly felt like an imposter, and the big goal that matters most: more meaningful conversations about money. He also gets practical with three clear invites—book him for your show or channel, leave an Amazon review, and order a copy fro...

I’ve been wrestling with a question for years: Why do I always call Jason? Jason is a friend of mine who always affirms my ideas. This essay and sketch was my attempt to confront confirmation bias head-on. We’re wired to seek agreement. But that’s how bad decisions happen. In this episode of Behavior Gap Radio, I share the story behind it, and how I try to push myself to invite dissonance instead...

I’ve always been fascinated by this idea: We feel about as much emotional connection to our future selves as we do to a stranger. That explains a lot, doesn’t it? It makes saving hard. It makes planning even harder. This is one of the ideas I explore in Your Money: Reimagining Wealth in 101 Simple Sketches, coming October 21, 2025. It’s sketch #82. Want to see more from the book? 📩 Just email me:...

There’s this old mountaineering strategy called siege style. You drag everything up the mountain: extra oxygen, fixed ropes, backup boots, food for weeks, a team of porters. It works. But it’s heavy. Slow. Complicated. Sometimes, it leaves a mess. Then came a new idea: alpine style. What’s the minimum amount of gear we can bring and still make it to the top? It’s lighter. Faster. Riskier, maybe. B...

When markets get scary, most people yell: DO SOMETHING! And most advisors respond with stats, charts, and long-term return arguments. But that’s not what people actually need. At least, not first. This is a behind-the-scenes look at one of my favorite essays in my new book, Your Money: Reimagining Wealth in 101 Simple Sketches. It’s called “Scary Markets Hugs.” Because before we talk about data an...

Every investor has felt it. The panic. The urge to act. The voice in your head saying: “Just get me out.” This is The Big Mistake. And if you’re not careful, it can undo years of thoughtful planning. In this video, I share the story behind one of my favorite sketches: The Big Mistake. This sketch and essay are #54 of 101 in my new book, Your Money: Reimagining Wealth in 101 Simple Sketches . 🎁 Wa...

This might be the simplest sketch I’ve ever made. It’s just four shapes and one word: Diversification. But if you’ve ever built a REAL portfolio, you know exactly what it means. Here’s the uncomfortable truth most people miss: If you’re diversified the right way, you’ll always own something you don’t like. In this behind-the-scenes video, I unpack why that’s true... and why it’s actually a good th...

In this episode of Behavior Gap Radio, Carl introduces a new framework he’s been exploring for decades: the discipline of fullness. Inspired by natural lifestyle advocate Tony Riddle’s audacious barefoot running project, Carl unpacks how living a full, intentional life isn’t about white-knuckled discipline or deprivation. Instead, it’s about filling your days with nourishing commitments—family, re...

After an unplanned two-month break, Carl returns to Behavior Gap Radio with reflections on routines, streaks, and what truly matters. In this episode, he shares how stepping away revealed the difference between serving a tool and letting a tool serve you. From creative practices to daily habits, Carl explores how to use routines in ways that support a meaningful life—without losing the plot along...

Most budgeting advice feels like punishment. That’s how it felt to me, too... until I realized something simple but powerful: 💡 Money’s natural state is motion. That’s why we call it currency! 💡 And what really matters? Paying attention to where it’s going. In this behind-the-scenes video, I talk about one of my favorite essays and sketches from my new book, Your Money: Reimagining Wealth in Sim...

We’ve been told to spend less. Cut back. Control ourselves. But what if we practiced spending better instead? This is my behind-the-scenes thinking that shaped essay #30 in my new book, Your Money, coming out in October 2025. The essay is called “The Spending Practice." This essay talks about guilt, values, and why learning to spend with intention might just be the most radical financial move you...

This essay is from my new book, "Your Money: Reimagining Wealth in Simple Sketches." It’s called “Enough Is Enough,” and in this episode, I unpack how we confuse more with better —and what it really means to have enough. It’s a story about investing, dessert, and clarity. Because enough can't be a number. If enough is a number, you'll never have enough. Enough is actually a state of being that we...

This essay might be one of the most important from my new book, "Your Money: Reimagining Wealth in Simple Sketches." It’s called "Life Meets Money" and it’s about what really drives good financial decisions. Not markets. Not headlines. But the messy, human stuff underneath: goals, timing, fear, meaning. This is my behind-the-scenes thinking that shaped essay #10 in the new book coming out in Octob...

In this episode, Carl asks a provocative question: What’s the minimum effective dose of money? Just like medicine or exercise, more isn’t always better, and sometimes it’s harmful. Instead of chasing endless income, Carl invites us to define the results we actually want—freedom, security, joy—and then ask: What’s the least amount of money needed to get there? Because maybe the most radical act in...

In this episode, Carl shares three quick stories—a successful entrepreneur feeling like a failure, a heartfelt compliment from his daughter, and a wildly accomplished friend still stuck in comparison. The punchline? Comparison is the thief of joy. But unlike most thieves, this one can be stopped. Carl invites you to join him in a “comparison audit” by asking: Who are you letting on your mental sco...

In this episode, Carl explores the quiet panic so many of us are feeling about the future, especially young adults and the parents who love them. From canceled programs to crumbling plans, what do you do when the ground keeps shifting? Carl makes the case for a new kind of planning, one rooted not in certainty but in resilience. Not prepping for one disaster but building a foundation that helps yo...

In a world of AI-generated books, endless content, and virtual everything… maybe the rarest thing isn’t more information—it’s real human connection. In this episode, Carl asks a provocative question: What if the answer isn’t to become more like a machine, but more like a human? Because connection—the kind that happens face-to-face, heart-to-heart—is becoming increasingly rare… and increasingly val...