Behavior Gap Radio: Exploring human behavior...with a Sharpie

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.

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?

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 and discipline, we need to talk about being human.

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 is 54 of 101 in my new book, Your Money: Reimagining Wealth in 101 Simple Sketches.

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.But the quality of the experience? Higher. Way higher.So here's my question:Are we climbing our financial mountains with siege mentality or alpine style?Because all that extra stuff—bank accounts you forgot about, old investment logins, tools you don't use, subscriptions you meant to cancel—can start to get in the way.It feels productive until it doesn't.At some point, the stuff stops adding value and starts subtracting from the experience.This sketch is just a simple downward sloping line: More stuff = Lower quality of experience.And if I'm honest?Sometimes I look at my own financial setup and think…“I might be dragging too much up the mountain.”This sketch is #76 in the new book. It's called Alpine Style Life. 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.

This might be the simplest sketch I've ever made.It's just five 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 thing.This sketch is part of my new book, Your Money: Reimagining Wealth in Simple Sketches, out October 2025.

Most budgeting advice feels like punishment.That's how it felt to me too... until I realized something simple but powerful:

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 the new book 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 can make.

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 have to practice. This is my behind-the-scenes thinking that shaped essay #20 in the new book coming out in October 2025.This is the essay:We don't know when to stop.I include myself in that.Sometimes, I stop by the grocery store, buy a pint of ice cream, and eat it.That's right. The whole thing.I've noticed a predictable pattern when I do this:Bite 1: Best thing ever.Bites 2–10: Really good.Bites 11–15: Good.Bites 16–20: Meh.Bites 21+: I'm sick.I keep repeating this experiment, hoping for a different result.This behavior is called diminishing marginal utility. It's not just about ice cream, but getting more of anything.Beyond a certain point, more stops making you feel better. If you keep going, more makes you sick.More becomes “too much.”The secret isn't getting more.It's knowing when to stop.

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 October 2025.This is the essay:Good financial decisions happen at the intersection of what's going on in your life and what's going on in the markets and the economy.We start with a simple question. Then we get into the details, the nuances, the exceptions and trade-offs. Suddenly, things get very complicated.It's complicated because two complex forces collide: your life and the markets. That intersection is where every good financial decision is made.

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 valuable.Connection is the new luxury.

In this episode of the Deep Shift series, Carl explores how tactical curiosity—like obsessing over budgeting apps or fueling strategies—often hides something deeper. What starts as a surface-level decision can lead to a powerful emotional insight. Maybe it's not about interest rates… maybe it's about fear, identity, or old family patterns. Carl walks us through why it's easier to talk spreadsheets than shame—and how simply asking, “Why are you asking?” can crack open the truth.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 the Deep Shift series, Carl names the chase we all know too well: tactical curiosity. The frantic hunt for the perfect app, book, or tool isn't really about solutions—it's often a way to avoid the deeper, scarier questions. This episode invites you to pause the chase and ask, “What am I really trying to solve for?” Because awareness—not another download—is where real change 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 this first episode of a new series, Carl introduces the Deep Shift framework—his attempt to map the real journey of change. It's not about picking the right tactic or finding more information, it's about uncovering what's blocking the doing. From tactical curiosity to deep ritual, Carl explores why lasting change starts below the surface… and invites you to walk through it with him.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 wrap-up to the Your Wise Money Friend series, Carl shares where the idea came from and why it matters. People don't want another financial plan—they want to feel okay. They want someone to walk with, someone who listens with golden-retriever-level curiosity. In this episode, Carl challenges us to become that kind of friend: no agenda, no judgment, just love, presence, and deep curiosity. Turns out you don't need to know anything about money to be a wise money friend. You just have to care.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/