Behavior Gap Radio

In this episode, Carl explores what happens to our sense of wonder as we grow up, take on responsibilities, and become the adults we were told to become. Somewhere between the endless thrill seeker and the fluorescent-light zombie, he wonders whether there’s a way to mature without losing the curiosity, awe, and aliveness we had as kids. It’s an exploration of growing up without losing the part of ourselves that still wants to chase thunderstorms, follow an unexpected trail, and notice the moon rising.

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In this episode, Carl reframes one of life’s biggest questions as a treasure hunt: discovering what matters enough to build your life around. Rather than treating uncertainty about purpose or what comes next as something heavy to solve, he explores what happens when we approach it with curiosity, wonder, and a willingness to follow the clues. Maybe the most interesting work in financial planning isn’t finding more money at all, but discovering the kind of treasure that gives our lives meaning.

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In this episode, Carl shares a surprising moment from a workshop where changing one small thing about a dollar sign changed how people felt about it. Nothing about their financial lives had changed, yet the emotional response did. That experience leaves Carl wondering how much of what money means to us was inherited, learned, or absorbed, and how much freedom we might have to paint something different on the canvas ourselves.

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In this episode, Carl shares the story of a couple who wondered what would happen if they stopped waiting for retirement to spend meaningful time with their kids. A simple question in a financial planning meeting turns a distant dream into a real decision, and Carl explores what happens when we find something that matters enough to reorganize our lives around it. It’s a story about commitment, unexpected tailwinds, and the quiet moment when “someday” becomes something we’re actually willing to do.

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In this episode, Carl turns Behavior Gap Radio back into an adventure journal and shares an uncomfortable moment of his own. A stranger at the gym, a beat-up car, and a surprising flash of smugness leave him curious about how quickly possessions and outward signs of money can distort the way we see ourselves and other people. Rather than trying to fix or judge the reaction, Carl asks a simpler question: Isn’t that interesting?

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In this episode, Carl explores a strange habit many of us have: using someone’s wealth as evidence they’re worth listening to. Why does knowing that someone sold a company or has a $400 million balance sheet suddenly make them seem smarter, wiser, or more interesting? Carl examines how easily authority in one area can leak into another, and why we may want to get much more careful about confusing financial success with intelligence, wisdom, or human worth.

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In this episode, Carl puts two very different paychecks side by side: a ski patroller earning an hourly wage in an expensive mountain town and an NFL quarterback earning tens of millions a year. He’s not arguing that either number is right or wrong. Instead, he asks a more interesting question about what markets actually measure, what they don’t, and what the enormous gap between price and human value might say about us.

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In this episode, Carl continues his exploration of absurdity by putting two realities side by side: Wealth at a scale that is almost impossible to comprehend and ordinary families struggling to afford a first home. Rather than arguing about who is right, who is wrong, or what the solution should be, Carl asks whether we can simply pay attention to the strange things we’ve learned to accept as normal, and perhaps start by being willing to call them what they are.

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In this episode, Carl questions a common belief among families with significant wealth: Helping adult children financially will somehow ruin them. When the next generation already knows a substantial inheritance is coming, does withholding help today really teach the lessons parents think it does? Carl explores how our experiences with money shape what we believe our children need, and why a different set of circumstances may require a different set of lessons.

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In this episode, Carl uses the current fight over the Kennedy Center as a jumping-off point for a much broader question: What is money really doing in the room? Looking beyond the politics, he explores how quickly a conversation that appears to be about money can become one about recognition, status, power, control, or even gratitude, and why noticing those forces in our own lives may tell us far more than the dollar amounts ever could.

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In this episode, Carl explores what happens when families avoid difficult conversations about money in an effort to avoid conflict. Through the example of inheritance, he looks at how silence can quietly turn into secrecy, scorekeeping, stories, and resentment—creating the very conflict everyone hoped to prevent. Carl offers two simple rules for bringing these conversations into the open and protecting something far more valuable than the money: the family itself.

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In this episode, Carl explores the hidden cost behind the things we admire and want to build. A beautiful business, creative project, or seemingly successful life can look very different once we understand the trade-offs happening behind the scenes. Carl reflects on why it’s not enough to ask what we want to create. We also have to ask what it will require from us, and whether we’re willing and able to pay that price.

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In this episode, Carl shares an unexpected discovery from a simple experiment in taking more time to rest. As his mind settles, his body seems to have something else to say, raising questions about the patterns our nervous systems may carry long after our thinking has changed. It’s a personal exploration of rest, risk, and what we can learn when we get quiet enough to notice what’s happening beneath the surface.

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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.

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In this short episode, Carl explores a deceptively simple question: What if more isn’t always the answer?

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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?

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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?

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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?

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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?

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In this episode, Carl continues his reflections on commitment and thresholds through one fascinating word: cleave. It can mean to hold tightly together, but it can also mean to split apart—a beautiful accident of language that captures something essential about meaningful commitments. Whether we’re entering a marriage, leaving a career, or choosing a new path, something is joined while something else must change shape, and Carl explores why that isn’t simply the cost of commitment but perhaps the very thing that makes commitment meaningful.

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In this episode, Carl continues his reflection on thresholds, exploring the tension between leaving and arriving as his daughter prepares to get married. Some opposites aren’t problems to solve but polarities to hold, where each side gives meaning to the other. A threshold gives us space to honor what is ending and welcome what is beginning, but eventually, we have to cross it, allowing the old relationship to change shape so we can fully step into what comes next.

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In this episode, Carl reflects on threshold moments as his daughter prepares to get married. These moments resist simple categories: they can be happy and sad, an ending and a beginning, a leaving and an arriving, all at once. Rather than rushing across the threshold, Carl explores what it means to stand there for a moment, honoring what is changing while welcoming what is becoming possible, and recognizing that a meaningful life is full of moments when something precious must change shape for something new to begin.

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In this episode, Carl reflects on how differently we can interpret the world when we’re tired, emotionally depleted, or “in the basement.” A harmless comment, a credit card statement, or a letter in the mail can suddenly feel threatening, even when nothing is actually wrong. Carl explores the growing space between stimulus and response, and why simply noticing our own state a little sooner may be one of the most valuable practices we can develop.

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In this episode, Carl continues his exploration of a different approach to marketing with a simple question: Where are you still smoking? Before worrying about SEO, websites, content, or the latest marketing tactic, he argues that we should fix the boring basics first: return the email, call people back, show up on time, do what you said you would do, and say thank you. It’s a reminder that some of the best marketing isn’t marketing at all. It’s simply doing the work well and taking care of the people already knocking on the door.

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In this episode, Carl begins an exploration of marketing with a provocative claim: most marketing advice is just success porn—a tidy story built after the fact about why something worked. After decades of chasing tactics, formulas, funnels, and experts, he offers a different approach he calls “the offering.” Instead of asking how to get more clients or capture more attention, what if marketing began with making work worth sharing and offering it to the world with care, craft, consistency, and generosity?

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In this episode, Carl explores the “normalization of deviance,” the unsettling way risky behavior can slowly begin to feel safe simply because nothing bad happened. From investing to riding motorcycles, repeated success outside our normal safety boundaries can teach us exactly the wrong lesson: we got away with it, so it must be okay. Carl offers a simple reminder worth carrying with us: Getting away with something isn’t evidence that it was safe. Sometimes it just means we got away with it.

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In this episode, Carl explores one of the most dangerous lessons we can learn about risk: nothing bad happened last time. Whether in investing, backcountry skiing, or everyday life, repeated exposure to risk without consequences can slowly convince us that we were safe all along. Carl reflects on how the absence of consequences can masquerade as evidence of safety, and why one of the most important practices in risk management is simply to remember what happened to those who weren’t so lucky.

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In this episode, Carl brings together many of the ideas he’s been exploring around risk, options, commitment, capital, and meaning to ask one central question: How do we come to know what matters enough to reorganize our lives around? He explores why discovering what matters may require more than introspection, how small experiments and meaningful risks can reveal what we truly care about, and why the real work begins when we start aligning our money, energy, time, and attention with those discoveries. It’s an exploration of what makes us come alive, what we’re willing to carry, and ho...

In this episode, Carl reflects on an unexpected physical response to hearing about the deliberate constraints that shaped the life of Herbert Simon. Despite an extraordinarily expansive intellectual life, Simon simplified everyday decisions around clothes, food, home, and routine, and something about that made Carl’s whole nervous system settle. It’s an exploration of constraints, freedom, and the possibility that making parts of life smaller and simpler can create more room for the things we care about most.

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In this episode, Carl explores one more possibility behind our desire to keep our options open: maybe we’re simply avoiding the feeling of letting something go. Whether it’s an old project, another career, a place we might someday live, or a different version of ourselves, closing the door can feel like a real loss. Carl reflects on the hidden cost of keeping those possibilities alive and asks a useful question: Am I preserving something genuinely valuable, or am I just avoiding the feeling of saying goodbye?

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