Behavior Gap Radio

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.

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/ 

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.

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.

📩 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.

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?

📩 Just email me: [email protected]. Use the subject line "Friend of Carl" and I’ll send you 7 of my favorite sketches and essays.

You can pre-order the book now. My recommendation? Order one copy from ​Amazon​ and one from ​your favorite local bookstore​!

Bulk orders (25+ copies): Use code YourMoney5 at checkout here 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: 🎥 ​You can watch the full recording.
 
We hope it sparks some meaningful conversations for you and those you care about.

And remember... the more clearly we can see our future selves, the more likely we are to make choices today they’ll thank us for.

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 using siege style 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. 📩 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​.

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 on YouTube here.​ We hope it sparks some meaningful conversations for you and those you care about.

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.

🎁 Want a preview of the book?
Email [email protected] with the subject line "Friend of Carl" and we’ll send you seven of my favorite sketches and essays in the book.

📚 Pre-order now:
My recommendation? One copy from Amazon and one from your favorite local bookstore!
• Amazon: https://www.amazon.com/Your-Money-Reimagining-Wealth-Sketches/dp/1804091715
• Local bookstores: https://bookshop.org/p/books/your-money-reimagining-wealth-in-97-simple-sketches-carl-richards/22111257?ean=9781804091715
• Bulk orders (25+ copies): Use code YourMoney5 at checkout for an additional 5% off the already discounted bulk order pricing: https://bulkbooks.com/products/your-money-reimagining-wealth-in-simple-sketches

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

🎁 Want a preview of the book?
Email [email protected] with the subject line "Friend of Carl" and we’ll send you seven of my favorite sketches and essays in the book.

📚 Pre-order now:
My recommendation? One copy from Amazon and one from your favorite local bookstore!
• Amazon: https://www.amazon.com/Your-Money-Reimagining-Wealth-Sketches/dp/1804091715
• Local bookstores: https://bookshop.org/p/books/your-money-reimagining-wealth-in-97-simple-sketches-carl-richards/22111257?ean=9781804091715
• Bulk orders (25+ copies): Use code YourMoney5 at checkout for an additional 5% off the already discounted bulk order pricing: https://bulkbooks.com/products/your-money-reimagining-wealth-in-simple-sketches

This might be the simplest sketch I’ve ever made.

It’s just four 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.

🎁 Want a preview of the book?
Email [email protected] with the subject line "Friend of Carl" and we’ll send you seven of my favorite sketches and essays in the book.

📚 Pre-order now:
My recommendation? One copy from Amazon and one from your favorite local bookstore!
• Amazon: https://www.amazon.com/Your-Money-Reimagining-Wealth-Sketches/dp/1804091715
• Local bookstores: https://bookshop.org/p/books/your-money-reimagining-wealth-in-97-simple-sketches-carl-richards/22111257?ean=9781804091715
• Bulk orders (25+ copies): Use code YourMoney5 at checkout for an additional 5% off the already discounted bulk order pricing: https://bulkbooks.com/products/your-money-reimagining-wealth-in-simple-sketches

In this episode of Behavior Gap Radio, Carl introduces a new framework he’s been exploring for decades: the discipline of fullness. Inspired by natural lifestyle advocate Tony Riddle’s audacious barefoot running project, Carl unpacks how living a full, intentional life isn’t about white-knuckled discipline or deprivation. Instead, it’s about filling your days with nourishing commitments—family, rest, meaningful work, movement—so there’s no space left for distractions. Tune in as Carl shares stories, analogies, and experiments to consider what it means to let fullness, not scarcity, shape your life.

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/ 

After an unplanned two-month break, Carl returns to Behavior Gap Radio with reflections on routines, streaks, and what truly matters. In this episode, he shares how stepping away revealed the difference between serving a tool and letting a tool serve you. From creative practices to daily habits, Carl explores how to use routines in ways that support a meaningful life—without losing the plot along the way.

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/