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.

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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 generate the highest-quality information for your next move. A short, practical reminder for anyone facing uncertainty.

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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 matters—and quietly leaves no room for what doesn’t.

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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: How can we systematically put ourselves at risk for good things to happen?

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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 just human. The work isn’t to fight those instincts, but to notice them with compassion and patience.

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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.

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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 the scariest terrain to navigate isn’t out there—it’s in your own heart.

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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 looks like a master plan was really just stumbling into survival.

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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 from your local bookstore—and previews what’s next here: putting yourself at risk, making decisions under uncertainty, and choosing which creative projects to pursue.

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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 of comfort.

This sketch is #92 in the new book. It’s called Stop Calling Jason. You’ll find it in ​Your Money: Reimagining Wealth in 101 Simple Sketches​, coming October 21, 2025.

If you want a preview, I’ve put together a beautifully designed excerpt with seven of my favorite essays and sketches.

📩 Just email [email protected] with the subject line "Friend of Carl" and we’ll send it to you.

You can pre-order the book now. My recommendation? Order one copy from ​Amazon​ and one from ​your favorite local bookstore​!
• Amazon
• Local bookstores
• Bulk orders (25+ copies): Don't forget to use code YourMoney5 at checkout for an additional 5% off the already discounted bulk order pricing!

We held a special book launch conversation on September 30 with New York Times money columnist Ron Lieber.

If you missed it live, good news:
🎥 ​Watch the full recording here: https://www.youtube.com/watch?v=n7PEAeb4n_4&

We hope it sparks some meaningful conversations for you and those you care about.