May 5

The Essential Skill We Should Have Learned in Childhood That Impacts Adulthood

There’s an essential skill we should have learned in childhood but never did.

As a shy Indian kid in a small Texas town, the idea of asking any girl, let alone the prettiest one in school, to dance scared the shi$3 out of me. So I asked my dad to buy me some sunglasses for the dance.

When he asked why, I said, “So that I look cool when I ask this girl to dance.” If it worked for Rick Schroeder in Silver Spoons, I figured it had to work for.

When I walked into the gym with my sunglasses on, I chickened out. I didn’t ask any girl to dance… FOR THE NEXT 20 YEARS.

I was so desperate to fit in, that I avoided doing anything that might make me stand out.

How the Essential Skill We Should have Have Learned in Childhood Impacts Our Lives

essential skill we should have learned in chlldhood
Photographer: Everton Vila | Source: Unsplash


Look at your life (your significant other, your jobs, your accomplishments, etc). Was there a single element that didn’t require you to take a risk? As Alison Schrager says in her book, “We must gamble to get what we want, even if it comes with the possibility of loss”.

We risk:

There’s not one part or area of life that isn’t impacted by our ability to take risks. But nobody teaches us how to take risks and recover from failure without destroying our self-esteem. Sadly, our education system and social conditioning actively discourage it.

Taking risks is an essential skill we should have learned in childhood. But, with age, we become more risk-averse and less curious. We start to crave security, comfort, and certainty. People actively discourage us from taking risks. This makes sense because we have more to lose (a home, a job, etc). But as your tolerance for risk goes down, so does the scope of what’s possible with your life.


Photographer: James Pond | Source: Unsplash


Rejection is an inevitable part of taking any kind of risk. But it’s such a painful emotion that we’ll do almost anything we can to avoid it. We’ll avoid taking a risk, even though the potential upside is so much greater than the downside.

When Indians negotiate, they are willing to ask for things that are absurd. They don’t even need the Jedi mind tricks of an FBI hostage negotiator. In their eyes, everything is negotiable. So, they don’t care if they look or sound insane.

  • The first time my grandmother came to the US, she tried to bargain with a cashier at Walmart. She didn’t understand why my mother was paying full price.
  • I always take my dad with me to buy a new car. He will go so far as to tell the salesperson to throw in a free car. And he can turn a 5000-dollar down payment into a 500-dollar one.

When we ask for something we want, the worst that someone can say is no. But when they do, we confuse fact and fiction. We assign meaning to every experience we have.

  • 27 publishers rejected Tim Ferriss’ best-selling book The Four-Hour Work Week. Imagine how different his life would be if he had let that mean that he wasn’t a good writer.
  • Even after a decade of running Unmistakable Creative, people still turn me down. But that doesn’t prevent me from reaching out to people I find interesting.

You’ll never get the things you truly want unless you’re willing to ask for them. That means exposing yourself to risk. It means getting back in touch with this essential skill we should have learned in childhood.

3 Illusions that Prevent us from taking Risks

This is an example of zoom burst photography. The zoom lens on a tripod mounted camera is turned to zoom in or out during a long exposure of a still object; ceating the illusion of motion
Photographer: Robert Zunikoff | Source: Unsplash

1. Control

One of the “bugs” in the human operating system is our attempt to control the uncontrollable. Focusing on things we can’t control is a recipe for stress and anxiety. We believe that we can control outcomes, but we can’t. All we can really control is our own actions and behavior.

2. Security

Security is the greatest of the three illusions. We think that by crossing off the checkboxes of society’s life plan, we’ll achieve security. But it doesn’t matter whether you choose a predictable path or take the scenic route. Nothing is guaranteed and anything is possible.

3. Safety

We seek safety to avoid risk. But the world is changing at such a rapid pace. New jobs emerge and old ones disappear. As the author Randy Gage says, risky is the new safe. In the long run, it’s safer to defy the status quo than it is to defend it.

Risk and progress are intertwined. You can’t have one without the other. It takes a risk for entrepreneurs to start companies and for inventors to bring new technology to market.

Regardless of your age or your current situation in life, you can increase your capacity for risk. Just because you were never taught about this essential skill you should have learned in childhood, it’s not too late to develop it.

But first, you have to understand the three types of risks.

Physical Risk

essential skill we should have leanred in childhood
Photographer: Priscilla Du Preez | Source: Unsplash


Learning how to walk is the first exposure to physical risk that most of us experience. If you have kids, then you know what an unforgettable moment it is to watch a baby’s first steps… until you realize your days of dining out are over for a while.

Yet every time a kid attempts to walk, there’s a risk of falling. Regardless of how many times babies fall, they will persist until they are walking. In her interview on the Unmistakable Creative, Sarah Peck described her son’s experience of walking as follows:

What’s really interesting is the amount of determination there is. At the beginning of human life, you see how innately curious and innately fascinated and just unbelievably determine they are. He tries something, it doesn’t work. He tries it again and again. I’m exhausted just watching him sometimes, but he never stopped.

We learn to crawl, walk, and run. By the time we’re running, adults around us are doing everything they can to reduce our physical risk, while we are do everything we can to increase it.

As I’ve come to understand with age, this is parental nature. That’s the reason that, no matter how old you get, your parents say, “text when you arrive.”

But everything from running around on a playground to playing sports comes with the possibility of physical risk. Cuts, bruises, and scrapes are a rite of passage in childhood. Nobody gets to adulthood without a few scars.

Then something happens… Rather than continue to develop this essential skill we should have learned in childhood, we do all we can to avoid using it.

Snowboarding and Surfing

With age, the bruises become more brutal, it hurts a bit more when we fall, and our tolerance for physical risk goes down.

I grew to HATE snowboarding in my 20’s. After 2 seasons, I told my friend “brown people and cold weather are an unnatural combo.” But now, at 41, surfing is my first love, and snowboarding is a wonderful mistress.

What changed? The euphoria of standing up on a wave was so intense; I was willing to endure anything to experience that feeling. I’ve definitely had some close calls in the water. There have been times when I thought I was going to drown.

But what 10 years of surfing and close to seven years of snowboarding have taught me is that the pleasure far outweighs the pain. And the fall is never as bad as you think it’s going to be.

Your ability to take physical risks will inevitably decline with age. But you don’t have to become an action sports athlete to take physical risks. Something as simple as a long walk or a yoga class could expand your capacity for risk. Step slightly outside of your comfort zone and you’ll quickly get back in touch with this essential skill you should have learned in childhood.

To add to this, physical risks also equip you to take creative risks. Moreover, they teach you how to respond rather than react to situations in other parts of your life. Somebody hating one of my blog posts is mild in comparison to getting pummelled by a 10-foot wave.

Emotional Risk

essential skill we should have learned in childhood
Photographer: Debby Hudson | Source: Unsplash

The success rate for meeting the right person is one in ten. Only after you have met nine other people does one appear who likes you back.” – Haemin Sunim, Love for Imperfect Things

Every relationship in your life from friendships to romantic love requires emotional risk. This is why the most important relationship in your life is the one you have with yourself. The strength of this relationship impacts your ability to take emotional risks in your relationship with others.

You probably remember when the line is drawn in junior high between popular kids and unpopular kids. Once you become aware of your social status, you come up with the list of all the people who are “out of your league.”

For me, it was the cheerleaders and girls on dance teams. From junior high to the end of college, none of the girls I “liked’ ever liked me. Because a few girls didn’t like me, I started to believe that all of them didn’t.

Because I had unrealistic expectations from watching a few too many romantic comedies, I stopped taking emotional risks.

  • I had the biggest crush on my English teacher’s daughter in the 8th grade. She also gave me every indication she would say yes if I asked her out on a date.
  • There was a girl in one of my classes during my freshman year of college who used to laugh at everything I said.

But I never asked either of them out on dates.

Because what we believe creates a filter for how we experience the world, we’re literally blind to opportunities that are right in front of us.

When emotional risks don’t live up to our expectations or get our hearts broken, we make permanent decisions as a result of temporary experiences. As my friend Brian said to me after a bad break up with an Indian girl, “You can’t rule out an entire race, particularly your own.”

We have to learn to take emotional risks to fall in love, make friends, and navigate the social dynamics of adulthood. And we have to do it without letting disappointments turn into disasters and depression. Emotional risk and social connection are birds of a feather.

If we want to experience the joy of connection, we have to take the emotional risk of rejection.

Creative Risk

When I work with creative people to bring their ideas to life, they have two fears:

  1. Their work will suck
  2. Other people won’t respond well

Because of evolution, we care a lot about what other people think.

But how the audience responds to your work is completely out of your control. The only thing you control is the effort you put into the process.

Take Seth Godin. People have said we’d need to invent him if he didn’t exist and called him a “cultural visionary.” Millions agree this is true today. But the further back you go into his body of work, the less this is the case. My favorite example is his book Titled Email Addresses of the Rich And Famous 


It’s not exactly the work of a “cultural visionary.” If you compare your creative work to someone else’s outcome, you’ll find it inadequate. But if you trace the progression of their work, you’ll start to see that everybody starts at zero.

Everybody sucks when they start. When you start anything new, you have to give yourself permission to suck. Otherwise, you’ll never get started.

Financial Risk

A few months ago, I interviewed a professional poker player named Alec Torelli. I asked him what his biggest loss was in one night. ONE night, he lost over two million dollars.

Imagine how that would feel for most people. For many people, that’s what they earn over the course of their careers. But what surprised me most was what he did to bounce back.

Rather than acting as if he’d, he lost, he decided to do what he’d do if he won: exercise, eat well, etc.

Of all the risks we take, this is the one that comes with the most anxiety because both the upsides and downside can be so big.

It’s a financial risk when you:

  • Attend a prestigious university and don’t know if it will help you get a job
  • Invest in a course, coach or mentor you aren’t sure will produce a result
  • Buy a house only to see its value decline

Every purchase you make is a financial risk, whether it’s a new pair of shorts or a meal at a restaurant

Want to become better at taking risks and making decisions? I’ll send you interviews with a professional poker player, an economist, and Google’s director of innovation. Click here


Strategies for Taking Risk

All in
Photographer: Keenan Constance | Source: Unsplash


Risk without strategy is recklessness. Driving without a seat belt, snowboarding without a helmet, or launching a product when data says it will fail doesn’t make you risk-tolerant. It makes you an idiot.

People who succeed when they take risks are strategic. They mitigate risk by thinking in bets, conducting experiments, and adjusting their actions accordingly.

1. Thinking in Bets

Often we confuse the quality of an outcome with the quality of our decisions. But we can avoid this by thinking in bets. There are three parts to any risk you take:

  1. Decision
  2. Outcome
  3. Probability of the Outcome

Let me demonstrate with an absurd example.

  1. Decision: Say I decide to ask a girl who has a boyfriend out on a date.
  2. Outcome: She says yes or no.
  3. Probability: Unless she hates her boyfriend, the probability she’ll say yes is zero.

In the case of the example above, it’s a terrible decision with an outcome that’s almost guaranteed.

But let’s look at a less ridiculous example:

  1. Decision: Write a blog post about why risk is an essential skill
  2. Outcome: People hate it or love it
  3. Probability: There’s a 50 percent chance that people will love it or hate it

In this case, writing the blog post is not a bad decision. It won’t lead to bankruptcy, jail time, or death (my litmus test for most risks).

2. Conducting Experiments

A well-designed experiment requires minimal time, effort, and resources. But it has the potential to provide you with invaluable feedback. In the words of our former podcast guest Alberto Savoia, you want to fail “Ferrari fast and Fiat cheap.”

Take my friend Gareth. He started a business with a $150 and a simple experiment that led to $10,000 in his first month.

  1. Record a Youtube Video
  2. Drive traffic to the video with some Google Ads
  3. Encourage people to book an appointment with him on a landing page

Today the business generates almost 50,000 dollars a month in revenue.

He made what the author Peter Sims calls a little bet.

3. Adjust Accordingly

Assuming you’ve been strategic with your risk and gathered valuable feedback, you can adjust accordingly.

For example, Chris Rock tests his material at open mic nights before a national tour. If you pay 100 dollars to see him you expect him to be funny. But seeing him at an open mic night is a pleasant surprise.

By testing the material in a low-stakes environment, he’s able to take a risk and adjust accordingly. When he hits the stage for a national tour, the material has already been proven.

A few years ago, I met an old guy at a coffee shop. Every time someone asked how he was doing, he’d say, “It’s the best day of my life.” Since I was having the worst day of my life, I asked why he kept saying that.

He told me, “At some point, I realized that there’s less time in front of me than there is behind me. So every day going forward is the best day of my life.”

Look back over your life. Think about every event that decreased your tolerance for risk. What did you miss out on? What did you not do because your fear of the downside outweighed the upside?

There may be less time in front of you than there is behind you. But that doesn’t mean it’s too late to take a risk that will lead to a more meaningful life.

Before you Go

Want to become better at taking risks and making decisions? I’ll send you interviews with a professional poker player, an economist, and Google’s director of innovation. Click here


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