In this episode of Behavior Gap Radio, Carl tackles an uncomfortable truth: Luck plays a bigger role in our lives—and our outcomes—than we like to admit. He explains why, in complex environments like markets, careers, and relationships, good decisions can lead to bad results and bad decisions can occasionally pay off. Through stories, including a man who gambled everything on one roulette spin, Carl illustrates the crucial distinction between skill and luck, and why the real work is building a repeatable decision-making process. Recognizing luck, he says, brings humility, compassion, and clearer thinking in uncertain terrain.
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In this episode of Behavior Gap Radio, Carl breaks down three words we often mix up when thinking about risk: danger, exposure, and vulnerability. Through a story about an elderly client worried about geopolitical news that had no real impact on her, he shows how easy it is to confuse “danger out there” with “risk to us.” Carl explains why understanding where the danger truly is, how exposed we are to it, and how vulnerable we’d be if it hits, can completely change our decision-making in markets, mountains, and everyday life.
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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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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 hello@behaviorgap.com 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.