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

In this episode, Carl turns the planning conversation toward current reality and asks a deceptively simple question: Where are you, really? After starting with purpose, values, and goals, he explains why honest planning can only begin once we locate ourselves clearly. Carl reframes balance sheets and net worth as stories, not just numbers, and shows why naming what you own and what you owe is an act of kindness, not judgment. This episode explores how radical honesty, done slowly and without shame, can turn vague anxiety into something workable and gives planning a real place to start.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 episode, Carl introduces the idea of “crunchy bits” and emotional resonance—those subtle moments in a conversation when something important is trying to surface. He explains how to notice the signals: changes in tone, pauses, defensiveness, laughter, body language, or even a shift you feel within yourself. Most importantly, Carl talks about the courage to slow down and hold space, rather than rushing past discomfort. This episode serves as a practical guide to the fine-brush work of real financial planning, where presence, patience, and trust create the conditions for meaning to emerge.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 episode of Behavior Gap Radio, Carl explains why goals should grow out of purpose, not the other way around. Rather than starting with numbers or aspirational targets, he shows how a clear sense of purpose gives goals meaning, flexibility, and durability. When goals emerge from purpose, they stop feeling like pressure or performance metrics and start acting as directional markers that can evolve without shame. Carl shares client stories to illustrate how purpose anchors goals, keeps them from becoming brittle, and reminds us that the point was never the goal itself. The point was living in alignment with what matters in the real world, where plans change and clarity is always provisional.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/ 

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.