Fear and Adventure: Why Encouraging Risky Behavior Will Save Us All


Safety is killing us. It is stifling. Nobody wants to take risks. Nobody wants to make the calls that have consequences should they not work out.

My observations and personal experience lead me to believe that, unless people have near mathematical certainty of a positive outcome, nobody wants to make a decision.

But why? And why does this matter?

It matters because life is risky. Being an entrepreneur is risky. Approaching that cute girl over there is risky. Moving to a different city is risky. And so is standing up and physically defending your loved ones and other innocents from harm.

Riskiness and rugged individualism are baked into the American way, but somewhere along the line this started to get viewed as a liability rather than an asset. I believe the common buzzword is “toxic.”

How we got this way is less of an important question–helicopter parents, “wear a helmet,” and all of that. More important is making sure that the next generation isn’t like us.

The wife and I took our soon-to-be four-year-old to a fun local kid’s amusement park the other day. He is very tall for his age, and much to his delight, is now able to go on many of the rides hitherto unavailable to him.

The kid didn’t stop.

Edaville, Carver Massachusetts.JPG

Roller-coasters, the big Ferris wheel, rides that shake, spin, tumble, and drop. He loved them all, laughing hysterically and throwing his hands in the air with each loop and plunge. If he’s had any fear of free-fall or heights, he hid it well.

It was great! There’s nothing like watching a little kid enjoy themselves. But it also made me think of a few things relating to my own life:

  • I never went on roller-coasters when I was a little kid.
  • To this day, I really don’t like roller-coasters and still kind of fear heights.
  • Much of my adult life has involved overcoming my aversion to risk-taking.

Are these things connected? Does a willingness to take physical risks translate into other kinds of risk-taking later in life, risk-taking in love, in business, and in thought?

I mean, I have a boy. Boys are crazy, right? They all have this impulse to make mischief, take things apart, and in general raise hell.

But there’s more to it than that.

These impulses, whether in boys or girls, are inborn but can also be squelched. 

They can be squelched by excessive safety.

They get squelched at our own peril. A society that’s afraid to take risks is a society that’s afraid to be great.

I’ve been beating this drum for a while now, but I see a generation gone haywire. I need to make sure that I don’t make the same cultural mistakes that lead to this with my son. Whether you call them “beta males” or another preferred epithet, there’s no doubt that traditional notions of masculinity and risk-taking necessary for American society to function in the kick-ass way we’re accustomed to are going the way of the dinosaur.

I have to make sure that my son never loses this impulse. This isn’t something that just hit my mind. It has been percolating for a while and informing my parenting choices. But something about sitting at the top of the Ferris wheel, watching my son point at the landscape, commenting how small everything looked with wonder in his voice and his eyes, crystallized things perfectly: What I’ve been doing, and what I should be doing.

Thomasland, Edaville Park, Carver, Massachusetts.JPG

I don’t claim to be a perfect parent, nor do I have THE SCIENCE to back these up. And these are male-centric since they’re derived from my personal experience with a boy. But here are some things I try to follow with my son to make sure he never loses that risky, devilish impulse:

Never say “What’s wrong with you?” Parents have a natural tendency–call it a cognitive bias–to think that little kids should act like little adults. This is ridiculous. It’s still a work-in-progress, but I’ve stopped saying this to my son. When my son does something completely absurd–brings a bucket of dirt inside the house and dumps it on the floor, sfor instance, or decides that it’s a great idea to start throwing stuff at the TV (which, to be fair, is a pretty good idea)–I have to take a deep breath, remind myself that he’s just curious about things, and let him know why his actions aren’t acceptable instead of making it sound like he’s defective.

There is nothing wrong or improper about the childish instinct to spoil, to destroy, or to see how far boundaries can be pushed. Kids don’t know better. They’re just curious.

Let him hurt himself (within reason). This one is tough, because it goes against the natural parental instinct to protect our children. But if my son is doing something risky, I let him finish his scenario to the end as long as the downside is on the order of magnitude of a skinned knee or a bruised shin. And afterwards, I make sure he gets back up and tries the thing again.

I’m convinced that a willingness to take physical risks does translate into a willingness to take other risks, and I don’t want to stifle that instinct in him.

Besides, you can always walk-off small bumps and bruises.

Protect the downside. I try to communicate to my son, in ways he can understand, why the safety measures we do take are important. Usually, trying to buckle his seatbelt or putting on sunscreen makes him impatient and antsy, asking “What are you doing, daddy?” But he has to know the why before I send him out into the world. “You can have all the fun you want, I just don’t want to you get sunburned.” “Play in the woods, but not over there, because that’s poison ivy and it will make you itchy.” And so on.

I found this principle articulated very well by Richard Branson in his 2012 book Like A Virgin: Secrets They Won’t Teach You at Business School, which, ironically, I read in business school. Branson talks about taking calculated risks. This is a cliche for a reason. It’s why people like Branson, Donald Trump, Warren Buffet, and Scott Adams, to name a few, are able to make risky moves that end up failing without completely ruining their business or personal finances.

Richard Branson As an adventurer I try to protect against the downside. I make sure I have covered as many eventualities as I can.

Is four too young for my son to understand these principles? Probably. But I’m trying to plant a seed now so that when he’s a little older he’ll remember what his boring old dad used to say.

Don’t project your neuroses. Another easy one to say but a difficult one to live. The amusement park rides are a perfect example for illustrating this: Just because I don’t like roller-coasters and other thrill rides doesn’t mean I have to make sure my son doesn’t either.

If he really wants to do something that I personally don’t care for, I’ll just have to strap on my big-boy pants and do it with him.

The things he gravitates to now may be indicators of what he is willing to devote the time to get skilled at later in life. And sinking time into something is a risk with significant opportunity costs. I’d like to make sure that he sinks the time into something he actually enjoys doing.

Our kids are a part of us, but it doesn’t mean they have to be clones.

Create time and space for mischief and destruction. Sometimes my son, normally easygoing, curious, and respectful, really just wants to trash things. And so I let him. Within reason.

I used to put a stop to this, but then asked myself: Why? Is anything really going to get broken beyond repair, or do I just not want to clean up after him?

Analyzing my own motivations made everything fall into place.

If he wants to destroy the huge Lego city he just built . . . if he decides to dump his (washable) paints into a big pile, stick his hands in them, and start coloring the walls . . . if he thinks it’d be fun to run the garden hose, make a pile of mud, and start jumping up and down as high as he can . . . I tend to let him.

It’s fun, and it’s good to get that energy out.

Dirt and paint can always be cleaned from skin and clothes.

Legos can always be rebuilt.

It’s much easier than rebuilding shattered confidence.

Follow me on Twitter @DaytimeRenegade

And check out my Instagram here.


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