Is Gambling a Valuable Life Skill?

Two major reasons why you should take calculated risks

Sackri Writes
4 min readFeb 6, 2021

Have you ever wondered how life might have turned out had you not taken a few risks? If you had not quit your job to run your own business? Or taken a year off to restructure your life?

Whether you have had to dive into financial uncertainty or emotional vulnerability, risks have no doubt been a necessary evil. In fact, decisions with a ninety percent possibility of success also have a ten percent probability of failure. Life will always be a gamble so we might as well learn to take calculated risks.

“There is freedom waiting for you,
On the breezes of the sky,
And you ask ‘What if I fall?’
Oh but my darling,
What if you fly?”

— Erin Hanson

Why Do We Need to Take Risks?

Think of a time you had to take a risk. No, not just any risk — the Marie Curie of risks. If it wasn’t a game changer or a page turner, think again. Mine, is the decision I made over a year ago to switch career paths. At the time, I was at the peak of my final year at the University of Dar es Salaam.

While most of my classmates were eager to graduate, I was sceptical about life after. I remember asking myself, “Is this really what I want to do?” and if not “What else is out there?”. So, I did what most people do when torn between two worlds — I wrote a Pro/Cons list which escalated to a dissertation. But that’s a story for another day. Looking back, I now realize how important it was to go out on a limb and take a leap of faith. Here’s why:

1. A life without regrets is a happy life

What do you think you’ll regret the most about your life? Not following your dreams? Yeah, me too. Perhaps you never gave that bakery idea a chance because you saw “potholes” down that road. Maybe you thought your paintings wouldn’t amount to much — despite your love for art. Or perhaps you never found the courage to fly out to her/him, to let them know how much they mean to you. Instead, you let them go about their lives while you wonder “what if?”.

“What if?” by Rostyslav Savchyn on Unsplash

Each of us has an ideal version of who we want to become or what we wish to pursue. When reflecting on our lives, we often wonder whether we are becoming the person we’d like to be. This is what shapes the regrets we have when we look through life’s windscreen. You see, failure is seldom the cause of regret. Doing nothing is what truly haunts you.

“Marry, you will regret it; don’t marry, you will also regret it; marry or don’t marry, you will regret it either way. Laugh at the world’s foolishness, you will regret it; weep over it, you will regret that too; laugh at the world’s foolishness or weep over it, you will regret both. This, gentlemen, is the essence of all philosophy.”

— Søren Kierkegaard

2. It is a great self-esteem booster

Learning is a major part of life. Failure can be a great teacher — if we are willing to look past the disappointment. This is essentially because in order to discover what works, you must learn what doesn’t work. Do you ever catch yourself fabricating deeply rooted strategies to avoid the risk of failure? What you need to remember in these instances is that taking risks: grants you the opportunity to explore, fail, grow and fail better. When you do this, you boost your self-confidence which in turn builds resilience to failure.

“When you take risks, you learn that there will be times when you succeed and there will be times when you fail, and both are equally important.”

— Ellen DeGeneres

While failure is inevitable, the experience we get need not go to waste. Who knows when the next rainy day might be? Yes, some risks should be avoided because the consequences could be catastrophic. However, with the guidance of the lessons we learnt, we can get better at taking risks.

“Fool me one time, shame on you,
Fool me twice, can’t put the blame on you,
Fool me three times, drop the peace signs,
Load the chopper, let it rain on you! “

— Jermaine L. Cole

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Sackri Writes
Sackri Writes

Written by Sackri Writes

Curious about the world and how to make the most of my time here. I write to think, feel and share my journey.

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