How To Play It “Safe” And Still Do Great Things

Growing up I was always told “Make sure you do something safe”. This was usually mixed with “We just want you to be happy, safe and stable”.

Being part of an immigrant Indian family that prioritized education, career and hard work - the “do something” was usually career-related and “want you to be” was usually related to prestige in society - usually something my extended family would think was respectable.

This type of culture led me to be pretty risk-averse growing up and play it “safe”. Everything my parents had said about safety made sense, so, I did everything that would increase my likelihood of success, I got good grades, kept my head down at school, and tried to make friends with only the smarter students. I wouldn’t even want to go out to a party in high school because that seemed risky to me. Eventually, all this landed me at university at one of the best business schools in Canada.

That’s when my illusion of safety began to shift. Slowly, the things I thought were safe & stable became different than my parents. They thought being an accountant or doctor was safe. I thought building assets & learning the skills to build a business was safe. They thought an arranged marriage was safe. I thought a marriage where you understood your partner thoroughly and had experienced parts of life with them would be far safer.

That was the first time I realized that safe choices are interpreted differently from person to person based on their experience. Navigating the prickly thornbush of my beliefs and my parent’s beliefs around safety was one of the most emotionally taxing experiences of my early life. It was also the first time I realized that you can control what you perceive to be a “safe choice” in your mind. By learning how to control what you perceive to be safe you can achieve incredible results in life because you can get yourself to do traditionally unsafe things.

Humans are always trying to trick ourselves into doing things we know we should. The best way to get yourself to do things is to lower the risk of failure and increase your likelihood of success. The safety of a close-to-guaranteed result is very compelling. We say we want to be "safe" but we usually don't know what that means. Usually, when people say they want safety, they mean "I want to know what is going to happen when I take these actions with 90% certainty".

Right? Knowing what will happen with certainty is usually what people look for when they say they want safety.

When I was in university, one of my roommates began playing poker and decided to leave school to pursue it full-time. A lot of our friends (at times, myself included) thought this was a huge risk and that he was giving up a lot. After chatting with him, he seemed surprisingly calm about the whole thing. He had been playing for a while, had seen great results, and had done considerably well financially. He saw little to no risk with him taking some time off to play poker for a bit.

This threw me for a bit of a loop. How could he see playing poker as a low-risk path? And why did I think it was a huge gamble? (Pun intended)

The difference was clear:

  • He was good at poker. I was not.

His skill set and understanding of the risk of taking on a poker lowered the feeling of risk.


That’s when I realized you can control what is a safe option & what isn’t through your learning and skills. So as you learn & the more you can predict what will happen - your feeling of safety increases. The feeling of safety is controllable.

The bad poker player (me) is concerned that poker is an uncontrollable gamble. The experienced player gets the odds, can weigh their odds of winning and losing and feels comfortable with their bet.

The inexperienced business owner is afraid of spending money on ads and hiring because it’s risky overhead. The experienced business owner understands there’s risk, and can decide how much they want to invest.

That’s not to say playing poker & building a business are not risky things. They both involve considerable risk. The difference here is that the experienced player & business owner have some experience to lean on that makes them feel confident doing it regardless of the risk involved.

Take any area of your life where you’d like to achieve something but feel worried about the risk involved. It can be anything; from meeting your partner’s family to starting a business to asking that attractive person out on a date. Anything that feels like an unsafe or risky endeavour is probably an area of your life where you’re missing a past result that’s positive enough to trick your brain into thinking that pursuing it is safe.

The inverse of this is to think of a scenario where an action you’re taking seems safe and simple to you but risky and worrisome to someone else - there’s usually some personal experience you’ve had that makes you think “Of course, I would do this due to x and x”.

The trick to getting yourself to do traditionally unsafe things is to build some sort of reference which logically makes you think “Based on my past experience, of course I should do this”.

There’s no measure to how successful a result needs to be to take you over the edge from thinking something is risky to safe - it needs to be whatever will convince your brain “Yep, the risk there is manageable”. That can vary for everyone. For leaving school for poker you might have to make an annual salary from your poker winnings or just win a few games. For building a business you might have to make your first few sales or learn how to manage a balance sheet.

But as long as you focus on building any sort of skillset or experience in the area of uncertainty you’re facing, you usually find that over an extended period, it feels more controllable and therefore safer.

You might not ever be able to convince other people of your perception of the risk. That’s usually a losing battle. What you want is to develop the ability to make good decisions based on what’s in front of you, make sure your lack of previous experience isn’t impairing your ability to analyze it and go get the little bit of validation you need to do the big & scary thing. You also don’t want your positive previous experience to taint the risk of taking something on - you just want to develop the ability to safely assess the risk involved accurately.

This is especially important if you’re ambitious and want to do great things in life because that usually involves taking risks. Your ability to assess risk accurately and inspire yourself to do it anyway will be important in the pursuit of your ambitious goals.

-Arry Pandher

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