The Inherent Risk of Playing It Safe

by | Mar 29, 2022

The Inherent Risk of Playing It Safe

Jack was out for his nightly walk when he popped into the local grocery mart to pick up some last minute items for that night’s dinner. Pizza for one, a six pack of IPA and the latest edition of Men’s Health. 

He approached the checkout counter and there she was. ‘Hannah’ read the blue oval badge on her vest. Tall, blonde, attractive—and no ring. Everything Jack had always dreamed about. 

He slid his haul onto the conveyor belt and looked down as Hannah scanned and bagged each item with perfection. Jack desperately wanted to flash his charming smile, but something stopped him in his tracks. 

He had never felt particularly handsome, although quite the opposite was true. He had also never felt particularly confident. Due in part to the time he asked a girl out in high school and got laughed at in front of his friends. 

The exchange of pleasantries was kept to a minimum and Jack walked out of the store and into his own head. “Why didn’t I say something”? “Why didn’t I at least smile”? 

This is the inherent risk of playing it safe.

We all have opportunities like this everyday, perhaps not as obvious, but opportunities just the same. Opportunities to chase our dreams that are squandered because we can’t pull the trigger. 

Playing it safe assures us that we won’t get hurt, that we won’t get laughed at, and that we won’t be embarrassed. It promises security, protection and immunity from the judgment of others. 

Perhaps you yourself have a similar story. That boy or girl at the grocery store that you never could muster up the courage to talk to. 

Or the amazing job offer that you turned down because you didn’t dare give up the steady paycheck at your mind-numbing desk job. 

Or the time you said “Thanks, but no thanks” to that free Hawaiian vacation because your cat, Mr Happy Pants, might get lonely while you’re gone. 

Opportunities are all around us and some only come once in a lifetime. We often pass on them though like we’ll get another chance some day.

“Some day when I lose this last 20 pounds”.

“Some day when I have more money saved up”.

“Some day when I can find a decent cat sitter”. 

But if that someday never comes we’re left wondering – What if? What would your life have been like if you did have the courage to talk to that hot girl/guy that day? Or if you did take out that small business loan to fund the tech startup you’d been dreaming about since you were a kid? 

The reason we don’t often wager on ourselves is the fear of failure. The fear of failure can, in and of itself, be paralyzing. Failure comes in many shapes and sizes too- embarrassment, financial loss, potential injury, disapproval from others, feline depression, etc. 

Having a fear of failure can prevent us from ever trying anything worthwhile in the first place, and the inherent risk is that we will never live life to our full potential. 

In economics, Loss Aversion is the tendency to prefer avoiding losses over acquiring equivalent gains. This tendency can be applied to many other areas of our lives as well, and it can be a real buzz kill. 

But what if you just told the fear of failure to fuck off once in a while and took a gamble anyways. Would it be the end of the world if things didn’t work out exactly as planned? There’s a risk vs reward factor to consider, but if the potential reward is greater than the potential loss, then it’s a no brainer. 

Next time you see an opportunity, go for it. Hedge your bet if you have to, but do something, anything, to at least try. Start small and take chances you wouldn’t normally take. 

Introduce yourself to that hottie next time by asking for directions to the gym. Ask your sister to watch the damn cat for you. I can promise that the reward of at least knowing you gave it a shot, is worth it. And if things do work out you’ll build confidence for the next time. 

Having never gambled at the expense of your happiness is going to be a painful pill to swallow when you look back at your life one day.

People will often rationalize with themselves that they shouldn’t try anything risky. “What if things go wrong”? When the real question they should be asking  is “What if things go right”?

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