Want to Get Smarter Fast? Get in Over Your Head

Carl Richards Behavior Gap Over Your Head

Being in over your head may be the best way to learn what you’re capable of. Consider the following example of someone we’ll call David. 

David doesn’t know if he’s capable of swimming, so he stands in the shallow end of the pool and splashes around a little. Cautiously, he moves to chest-deep water and tries kicking his legs. When he gets scared, he stops kicking and stands up again. 

Then, someone grabs him and tosses him into the deep end of the pool. David figures out quickly how to swim (while that someone stands by just in case).

Luckily, most things in life won’t cause you to drown if you fail. You might end up embarrassed and scared. But there’s also the chance that you might suddenly find yourself swimming. 


I’ve had this experience over and over again. In fact, I’ve learned to prefer being in over my head. It’s definitely scary; that never changes. But it also forces me to perform in ways the shallow end never does. I go from thinking I’m capable of “x” to very quickly performing twice or three times that amount — and sometimes even 10x. 

Think of being in over your head as a little magic box. In one side goes the old you and out the other side comes a 2x or 10x version of yourself. 

This column, titled Want to Get Smarter Fast? Get In Over Your Head, originally appeared in The New York Times on September 25, 2017.

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Will you try something for me real quick?

Make a mental list of the things you REALLY want to be spending your money on. You know, things you value deeply. My list includes security, time with my family, and service in my community.

Now, gently compare that list to the way you ACTUALLY spend your money.

If you’re human, that exercise probably hurt a little bit because there is almost always a gap between what we value and how we spend our money.

I’ve been exploring that gap for 20 years, and closing it is the focus of my work.

“Carl gets the relationship between money and feelings better
than anyone on the planet.”
– Ron Lieber, New York Times

If that sounds interesting to you… you’ve come to the right place.

I've spent years looking for the best way to share my work. I’ve tried Twitter, Facebook Groups, blogging with comments, courier pigeons… everything. I've come to realize that nothing beats a well-crafted letter delivered to your inbox once a week and your ability to hit reply and start a conversation.

So each week I send a short email discussing topics like money, creativity, and happiness along with a simple sketch. And if I get it right, it will take you less than two minutes to read, but you'll be thinking about it all day.

"I love Carl's hand-drawn sketches. They feel so personal and immediate… like he couldn't wait to scrawl down whatever insight had just popped into that lightning-fast brain of his…"

– Kara Cutruzzula, Brass Ring Daily

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