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

In this episode, Carl reframes planning as a living practice rather than a one-time event, arguing that the real work of planning is the ongoing process of aligning your use of capital with what matters most as life and priorities change. He explores how treating plans as fixed predictions creates pressure, shame, and anxiety, while viewing planning as a rhythm of orienting, acting, learning, and adjusting allows us to stay grounded in reality. Planning, he suggests, isn't about being right forever. It's about being a little less wrong over time and building a sustainable way to navigate uncertainty.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 challenges the idea that resilience is about toughness or enduring pain, arguing instead that real resilience comes from thoughtful design that avoids unnecessary exposure in the first place. Using a powerful backcountry skiing analogy, he explains how shifting from managing danger to choosing safer terrain reframed his understanding of risk, joy, and sustainability. The lesson carries directly into planning and life: Resilience isn't about surviving fragile systems through grit, but about building plans with margin and guardrails so failure is survivable and courage isn't constantly required.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 expands the idea of planning beyond money to include the four forms of capital we're always spending: money, energy, time, and attention. He explains why plans that only optimize for dollars can look great on paper and still fail in real life, especially when invisible costs like exhaustion, distraction, or resentment go unexamined. Through simple, human examples, Carl argues that attention is the true currency of meaning and relationships, and that real planning is about aligning how we use all of our capital with what actually matters to us.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 pauses his planning series to explore the idea behind one of his favorite sketches from his new book: The Four Sources of Capital. Prompted by a thoughtful LinkedIn question, he unpacks why money, energy, time, and attention deserve to be treated as distinct—and why attention may be the most valuable of all. Using a simple skiing example, Carl shows how we can spend money, time, and energy without ever really being present, and how attention is what turns activity into meaning. At its core, this episode is a reflection on why attention is the true currency of meaningful experiences and lasting relationships.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 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.