The Man In The Car Paradox: A Lesson In Wealth For Younger Generations

The other day, I was driving with my 6-year-old son, Colt, when we pulled up next to a bright red Ferrari at a stoplight. His eyes lit up.

“Whoa! That guy must be so rich! So cool!” he said.

I smiled and asked, “Do you think he’s cool—or do you think the car is cool?”

He paused for a moment, thinking it through.

“The car!” he said

Exactly. That’s the Man in the Car Paradox in action. We instinctively associate flashy things with success, but we’re usually admiring the object—not the person behind it.

I’m a little embarrassed to admit it took me years to internalize that truth. Now, I’m trying to help my kids grasp it early.

That thought—“If I had that car, people would think I’m cool”—needs to shift into something healthier:

“That’s a fun toy. Maybe I’ll buy one someday, but I know real wealth is what you don’t see. Real wealth is made up of the things money can’t buy.”

Like any meaningful lesson, this one will take repetition. I’m fully expecting eye rolls and shrugged shoulders as they grow—but I’ll keep reinforcing the idea that true financial wealth is freedom.

Freedom to say no.

Freedom from paycheck-to-paycheck stress.

Freedom from the pressure to impress.

It’s having money quietly working in the background—investments growing, options expanding, and your time truly being your own.

There are technical steps to reach that first level of financial independence—but the higher levels go far beyond money.

I deeply admire so many of our clients who’ve “won the game.” Yes, they might own beautiful things—homes, cars, vacations—but they’re not defined by them. They have nothing to prove.

They’ve moved on to deeper questions:

What is enough? What is my why? What are my family’s values?

Those are the questions I want my kids—and all of us—to be asking.

-Written by Christopher Whitaker, CFP®, AIF®, Chief Wealth Manager

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