The Benefits of Thinking Like A Child

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Here is my weekly email with some insights and ideas pulled from conversations I had on my podcast.

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The Benefits of Thinking Like A Child

“When you’re a kid, you don’t have boundaries like we do as adults. We haven’t been tainted. We haven’t had enough people in our lives tell us we can’t do things when we’re a child.” ~ Chris Naugle

How often do you allow yourself to feel completely free of responsibilities and expectations? Do you ever pretend, even for a moment, that you don’t have a care in the world? 

I rarely do, if ever. I feel as though our propensity for freedom falls away as we age. We become more and more bogged down by the weight of the world as time goes on, and it seems that few of us ever find our way back to that carefree state. 

As it turns out, we’d be far better off if we could. Children are free of self-imposed limitations. They live in the moment; risk-taking is their way of life. They’re not afraid to look foolish, and they don’t hold back from trying new things. 

I recently spoke with someone who I felt retained a lot of these child-like qualities through entrepreneurship. Chris Naugle is a pro snowboarder, a serial founder, and America’s number one Money Mentor – but he grew up with no money at all, and had to make ends meet. Let’s hear how his story began.

Hustling From Day One

A far cry from the glamorous entrepreneurial dream, Chris grew up in a lower middle class family. His dad was an alcoholic and mostly nonexistent in his life. Thankfully, though, Chris had an incredible mother who instilled some amazing values in him from the get-go.

“We didn’t have money. We didn’t have resources. So if I wanted things, my mom taught me to draw them. I was always an artistic kid. Whether it was a skateboard I wanted, or a BMX, my mom would just say, ‘go draw it out. Show me what it looks like.’”

I loved hearing these little anecdotes from Chris’s childhood; it gives us a glimpse into not only the life he’s lived, but also the events that shaped his unique and admirable mindset. His entrepreneurial spirit was certainly there from day one. 

“My grandparents lived in a mobile home park. So I would go out there, and I would go around to the neighbors and ask if they needed weeding, or their windows cleaned. I’m like five, six years old at this point; I’d give the money to my mom, and she’d put it in this box.”

What a go-getter! Can you imagine voluntarily cleaning windows at five years old? That’s some true gumption. And it didn’t stop there – Chris also told me about one of the defining moments of his childhood, which was digging his own fishpond in the backyard. 

“Every single day after school, I went out there with a wheelbarrow and a shovel. And I just dug, and I dug, and I dug, and I dug, and I ended up digging a pond. It started with the idea, then thinking it over, and then taking action. Digging a pond is no small task.”

(Yes, Chris did end up putting actual live fish in the pond. No, they didn’t take the bait a second time around.)

Chris Becomes a Snowboarding Sensation

A significant part of Chris’s career and life has been spent on the slopes. He’s a professional snowboarder, and has been from the age of about 18 or 19. But getting there was no walk in the park – especially with limited funds and access. 

“Living in Buffalo, New York is not the mecca for snowboarding. I didn’t have money to buy lift tickets, but I would take that board up the street and build a jump on the hill.”

Once again, Chris strikes with his entrepreneurial spirit and innovative mind. Hitting a homemade jump wasn’t quite as glamorous as going up to the ski resort – but it did the job. A few months later, he was finally able to try boarding on a real slope.

“I remember my first run – I hated it. This probably would have been one of the first times I was willing to give up on something.” Lucky he didn’t, because snowboarding turned out to be Chris’s ultimate passion.

“I came up with the crazy idea that I’m going to be a pro snowboarder. I’m watching the VHS tapes. I’m looking at all these photos of my heroes, and I remember thinking, ‘I want what they have. I want to do what they’re doing.’” 

Supporting the Dream

Of course, to become a professional at anything, you need money – whether it’s for traveling to competitions, buying gear, or getting by on the road. Chris needed to figure out exactly where he was going to get the funds from. His answer? Launching the Phat Clothing Company.

“I started making shirts and sold them out of my backpack, and then I got my friends to start selling them out of their backpacks. One year later, we had three seamstresses, and I sold my clothing on the road.”

It wasn’t long before Chris wished for his own store; one he could attend to every morning, and then lock up to hit the slopes in the afternoon. 

“I just had to have that. I needed that lifestyle business. And that goal I found out would take about 70,000 bucks.”

With help from his mother, and using anything he owned as collateral for a loan, Chris eventually secured his first store – and suddenly, he was well on his way to supporting the professional career of his dreams. 

“Snowboarding was my life; it was all I thought about, and all I cared about. So everything was just a means to that end. A skateboard-snowboard shop embodied my ‘why’.”

What Made Chris So Successful?

I didn’t have time to cover his whole origin story, and there are a few key details you should be aware of before we move forward:

  • Chris went on to work as a financial advisor for Wall Street; he dabbled in real estate investing, and took risks during the recession that led to an accumulation of some pretty serious debt. 
  • He rose from the ashes, though, and is now the proud founder of 16 companies, with his businesses being featured in Forbes, ABC, and House Hunters. 
  • Chris is currently the co-founder and CEO of FlipOut Academy™, founder of The Money School™, and Money Mentor for The Money Multiplier.

You’ll notice that I chose to give his childhood stories significantly more spotlight than his later business achievements. Don’t get me wrong, the latter are incredible – you can hear all about them in the full podcast episode – but I focused on his childhood for a reason. 

Children, in all their wide-eyed naivety and flourishing imagination, are some of the most innovative people we’ll ever be able to observe. I have no doubt that Chris’s story brought up memories for many of you listening; moments when you invented something as a child, or solved a problem in an unconventional way. 

This is what I wanted to talk about in today’s newsletter – what it means to act on your ideas with all the enthusiasm of a child, and how taking that approach can help you overcome barriers like imposter syndrome.

Let’s take a closer look.

The Superior Psychology of Kids

“As a child, we don’t have limitations. We don’t have barriers. Many of us let other people’s failed dreams dictate where we’re going to go in life.”

I know, I know. Kids are pretty silly at times. If we all decided to revert to our younger selves, the world would probably fall apart. But Chris is right about one thing – adults are far too reliant on other people’s experiences and expectations in order to feel valid.

Take one look at the modern workplace and it’s easy to see how this happens. We’re so bogged down by rules, processes and the need to meet targets that we forget why we’re doing any of it in the first place. We become scared to take risks, or even try something new lest we fail and are ridiculed by our peers.

There’s also a deeper psychological reason, though, and it stems from our self-concept. Life coach and counselor Michael Formica explains it like this:

  • Each of us has a ‘self-concept‘ based on the experiences we’ve had and the way we’ve been treated by others.
  • This self-concept is like a set of glasses that we see the world through.
  • If our self-concept is tainted by failed risks or negative experiences, we’ll be more likely to see risks as dangerous and to shy away from them.

In other words, we become prisoners of our own past failures. I suppose this does make evolutionary sense – if we get burned by a hot stove, we’re unlikely to put our hand back on it. But when it comes to business, this kind of thinking can really hold us back.

It also explains why kids are the total opposite when it comes to taking risks. Their self-concept has hardly even had time to appear, let alone develop negative biases. And since they don’t have the same kind of experience or expectations that adults do, they’re far more likely to take risks and try new things.

The Role of our Frontal Cortex

It turns out there’s also a neurological reason for this difference in thinking. Professor and researcher, Leonardo C. de Souza, has studied extensively into the role of our frontal cortex in creativity; it’s fascinating that this area of the brain doesn’t even fully develop until we reach our twenties.

This part of the brain is responsible for things like planning and decision-making, and as de Souza explains, it’s also responsible for inhibiting certain behaviors. In other words, it helps us to think rationally and make sound decisions.

However, this comes at a cost; when our frontal cortex is more active, we’re less likely to take risks or be creative. And guess when that part of our brain is most active? That’s right – during adulthood. Everything becomes a little more rational and a little less fun. 

So, Why Is This Relevant?

The reason I started thinking about all of this in the first place is because I was absolutely blown away by Chris’s mindset. I’m floored at how, even from such a young age, he was nurtured to find his own solutions and do things unconventionally. 

It was incredibly sweet to hear his affection toward his mother, who undoubtedly shaped his perspective on business (and life) by asking him to visualize his dreams and always think big. 

I feel like there’s something inherently creative about people who grow up without money, too. 

“When you think about a pro snowboarder, you think they’re traveling around doing all these events. I didn’t have that luxury. I didn’t have the money. My early years were spent learning tricks in the summer on a trampoline.”

Hearing about how Chris carried this resourcefulness and creativity into his business endeavors made me want to understand how he thinks, and how I can do the same. What does it take to embody the intelligence and social skills of an adult, but the fearlessness and creativity of a child? 

How To Channel Your Inner Child

I came across something interesting whilst researching for today’s newsletter: Dr. Donna Maria Romeo, an anthropological consultant with McKinney, actually runs workshops with the aim of helping business people channel their inner child

Romeo believes that by doing so, we can liberate the parts of our brain that are blocked by stress and anxiety, making us more productive, efficient and happier employees. 

Here are some of the challenges her participants are faced with during the workshops:

  • Owning their assumptions. Participants are challenged to identify and call out any split-second assumptions they make about themselves and others.
  • Asking more questions. “Like anthropologists, young children don’t presume to hold prior knowledge about the world.” Participants are encouraged to ask questions about everything – even the obvious.
  • Immersion and observation. To channel their inner child, participants are asked to immerse themselves in an environment, taking in as much information as possible without judging it.
  • Noticing anything and everything. According to Romeo, the most creative, child-like thinkers are the ones who can see possibility and opportunity in everything.

While some of these tasks may seem daunting, or even impossible, at first glance – they actually make a lot of sense. I even remember exhibiting some of these behaviors as a child; it’s funny how we’re natural-born innovators without even realizing it. 

Mistakes Make You A Better Entrepreneur

One of the best things about children is that they’re not afraid to make mistakes. And making mistakes is actually one of the most important aspects of being an entrepreneur. 

Chris’s biggest mistake in his early career was taking out too many loans on real estate, and he paid an enormous price for it – debilitating debt, the temporary loss of his relationship, and having to start over almost from scratch. 

But making mistakes is a common theme across some of the most successful entrepreneurs. Milton Hershey launched two failed candy shops before his third one took off. Elon Musk lost all of his money from the SpaceX rocket explosions. James Dyson created 5,127 different (failed) vacuum prototypes before he finally got it right. 

The key is not in the mistakes themselves, but in the effect those mistakes have on our psyche. It’s like building your immunity to a poison; the more you’re exposed to failure, the less it feels like an unwanted substance, and the more it becomes a part of your journey. 

In fact, some people believe that making mistakes is actually essential to becoming a successful entrepreneur. If you never fail, it means you’re not taking enough risks – and without risk, there’s no room for growth. 

Next Steps

With all of this in mind, I’ve got some ideas on how I’d go about thinking more like a child. Hey, we’ve all been there before – it’s just a matter of calling back on those memories and re-learning how to see the world through childlike eyes. 

1. Embrace absurdity.

As Chris explained to me, the very best and most successful people are those who go out of their way to create something new. They’re not conforming to norms or expectations; they’re doing their own thing and making a name for themselves. 

“If you look at 20-year-olds, and you ask them all, ‘Are you going to be successful at the age of 60?’ Every one of them 100 percent will say yes. Take those same 20-year-olds, but now they’re 60 years old; statistics will prove that only one of them is wealthy, and only five of them would be considered financially successful.”

Insane, right?

“The difference between success and failure comes down to one thing. Five of them created something; they went out there, and they created, and they shut everything else out. The others gave into other people’s failed realities. They conformed.”

2. Focus on your ‘why’.

As a kid, your day-to-day decisions are solely based on your wants and needs – not on the expectations of others. And while you might not be able to get away with that as an adult, you can still use your ‘why’ as a compass to guide your actions. 

Your ‘why’ is the motivating factor behind everything you do; it’s what drives you to get out of bed in the morning and face the day. And when you’re able to connect with that ‘why’, it becomes a lot easier to make decisions (even if they’re not the ones everyone else wants you to make.) 

Chris’s ‘why’, for instance, was his snowboarding career. He let that be his north star.

“I didn’t care about being an entrepreneur. I didn’t even know what that was. All I wanted was enough money to be able to travel…”

Thirty-something years later, he’s been all over the world as a professional snowboarder. So something tells me he made the right decision. 

3. Start with a clean slate. 

A frustrating part of being in business is that we fall into a set of workplace customs. Having problems with your client relationships? There’s a bigger and better CRM software out there that can help you. Hiring process taking too long? Let’s just outsource it to a staffing agency. 

We get used to certain jargon, too. When employee performance is going south, it’s because they’re not being ‘coachable.’ They’re going through ‘growth pains.’ They need more ‘bandwidth’, we say, and then proceed to offer half-hearted feedback that does nothing to help the situation. 

In order to start thinking like a child, we need to forget all of that nonsense and start from scratch. If something’s not working, don’t just accept it – try to find a different way of doing things. And I mean completely different. 

Something I like to do when I’m feeling analysis paralysis is to shut out all external ideas for a whole week. That means no podcasts, no books, no articles, no conversations with people in my industry. I just sit down and try to come up with my own solutions to the problem at hand. 

And more often than not, I find that a lot of the answers I’m looking for are right in front of me. 


Writing this newsletter was more challenging than I expected it to be, and maybe that’s reflective of how strange it feels to think like a child. It takes real effort to shed your biases and preconceived notions, especially when you’ve spent your whole life building them up. 

But it’s worth it. Because when you’re able to think like a child, the world becomes a lot more interesting – and a lot less scary. And, if you’re anything like Chris, it becomes a world of opportunity rather than scarcity. 

If you’re as intrigued by Chris’s story as I was, I highly recommend going back to listen to his full interview on the Success Story Podcast. There are so many nuggets of wisdom in there; I guarantee you’ll come away with a new perspective on life, money, and business.

Thanks for reading, and I’ll see you next week!

Success Story Podcast

If you like the content in this newsletter, I host a Top 10 Business podcast, (with over 20m downloads) called “Success Story”, where I interview entrepreneurs, executives and other high performing individuals so you can learn lessons and insights from the world-renowned leaders.

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