The Rollercoaster of Life: Risk, Reward, and Lessons for the Young …. Part One or The Brutal Art of Gambling

Life is a wild rollercoaster ride, filled with exciting twists and turns that shape our paths. Yet, many folks are blissfully unaware of this thrilling adventure, stuck in the cozy groove of their everyday lives. By the time they finally realize that life is a bit like a high-stakes game show, it’s often hilariously late in the game. They’ve already made some questionable choices, like picking the wrong door or choosing the mystery box instead of cash. Now, they’re left to navigate the quirky outcomes of mediocrity or, at worst, a comedic disaster. It’s an endless game of poker where the chips are as high as the sky, and folding is not an option. Many think that only the savviest and wittiest players can dance through life’s challenging and amusing landscape, coming out as the champions with the best stories to tell!

Don’t get me wrong. There are countless folks all over the world who find joy without swimming in piles of cash or having a trophy room full of accolades. What’s hilariously ironic to me is that they also jumped onto the roulette wheel of life, maybe without even realizing it, just by chasing a different kind of jackpot. Perhaps they took a wild gamble and decided to prioritize family, culture, charity, religion or kindness over the never-ending rat race for money. But let’s not kid ourselves—they still put something valuable on the line to hit that happiness jackpot.

The individuals who, sadly, never achieved their dreams often stumbled because they didn’t fully understand the level of commitment needed to reach their goals. Some may not have had the knowledge to navigate the complex balance of risks and rewards. Others understood it but perhaps felt too overwhelmed or unmotivated to take action. Regardless of the reason, taking risks was a significant factor in their journey, much like it was a key to success for those who achieved their dreams.

Indeed, taking risks is a powerful and constant force at the heart of everyone’s quest for success. It plays a significant role in decision-making, offering the excitement of new opportunities and the hope of success. At the same time, it can challenge stability, introducing elements of unpredictability and change in the pursuit of one’s aspirations.

Fortune showered me with its favor, steering me toward the perfect people and opportunities at precisely the right times in my life. I was incredibly lucky to break free from the soul-crushing grip of the corporate world at a relatively young age, while many of my colleagues remained ensnared in its relentless clutches. As I surveyed my surroundings a few years ago, I saw too many friends inching closer to Medicare eligibility, still shackled by crushing obligations and responsibilities, their lives dictated by what they “must” do rather than what they desperately longed for. It was a brutal reminder of how fragile luck truly is and how easily it can vanish from our grasp, leaving us all in its wake.

As I look back on my life, my mind is filled with images of over seventy years of friends and colleagues. Each face reflects shared experiences, as we all walked similar paths, attended the same key events, had similar education, and worked in the same companies. However, while many simply absorbed this information as entertainment or fleeting interests, there were a few among us who saw it with striking clarity. We recognized untapped potential, a strategic arsenal to use in the harsh arena of life.

This knowledge was a weapon, a double-edged sword that both excited and frightened me, balanced on the edge of fate. The exhilarating thrill of taking bold risks, aware that a single wrong move could ruin everything, was irresistible. Those of us who thrived on the adrenaline of risk taking, technology, probabilities, data, and the truth/success those elements could provide, questioned whether our insider gambling knowledge would be our salvation or downfall.

My personal gambles were as relentless as a toddler’s quest for candy, and I was constantly flabbergasted by those who couldn’t quite grasp what I thought were the ABCs of risk and reward. Picture this: my grand entrance into the corporate world in 1973. My wife of now 51 years and I will never forget the jaw-drop moment when my first weekly paycheck appeared—a whopping $300. Sure, that was the going rate for an underwriter trainee, but back then, the average home was a bargain at $32,500, compared to today’s wallet-busting $355,000. In those groovy early 70s, I was just beginning to dabble in the art of gambling, blissfully unaware that I was about as clueless as a cat chasing its own tail.

I stayed with my first employer, diligently clawing my way up the corporate ladder, rung by painstaking rung. After a decade of dedication, marked by an average salary increase of over 10% annually, I believed I was thriving, still deeply anchored in the familiar neighborhood where I had spent my childhood. Simply put, I was naively nestled in a comforting cocoon of mediocrity, blissfully unaware of the vast world and opportunities that stretched beyond my immediate horizon.

Then came the great enlightenment, like a light bulb going off in a cartoon character’s head. I dove headfirst into the thrilling world of early computing, probabilities and statistics, because who needs adrenaline when you can have math, right? Reports became my bedtime stories, and soon I could predict risk and reward better than a weatherman predicts rain. I even sacrificed a week of vacation to haunt the Elgin Illinois library, analyzing horse racing results for the Arlington Park racetrack. Yep, I was the nerdy ghost of library past, developing my own “normalized speed ratings”—a crucial skill for anyone who wants to gamble on horses without actually knowing anything about them.

While I was knee-deep in risk assessments and reading Ayn Rand’s “Atlas Shrugged” (because who doesn’t want a little philosophical debate with their coffee?), I stumbled upon some interesting studies. One study was as clear as a neon sign in Vegas: changing jobs could rocket your salary increases compared to staying put like a barnacle on a ship. Yes, just one job change could turn into 2 1/2 years of normal career salary growth in a blink of an eye. So, I embraced career gambles like a professional poker player. Now, at the ripe age of 73, my family and I have lived in 12 different homes and 6 cities from coast to coast, each move a nod to my relentless pursuit of opportunity, learning, and the perfect pizza slice in every zip code.

I also found that gambling is deeply embedded in the corporate world, masquerading as seemingly respectable activities. It hides under names like risk-taking, decision-making, purchasing, investing, or underwriting in the insurance sector. Yet, at its heart, it is nothing but gambling. People are perpetually taking risks and placing bets, often oblivious to the fact. Some vehemently deny this gambling reality to preserve their illusion of cultural or business integrity, but this denial only blinds them to the complex intricacies and unspoken “rules” of the high-stakes game they are enmeshed in.

From the gleaming, high-stakes boardrooms of corporate America, to the thunderous, relentless grind of factories where operators sweat over their machines, to the fiercely competitive arenas where athletes push themselves to the brink, to the fervent congregations within religious organizations, to the insidious spread of misinformation wreaking havoc on nutrition and health, to the dazzling, adrenaline-fueled casinos and chaotic sports books, to the gritty, timeworn racetracks scattered across the nation. In all these arenas, the mastery of data translation and the ability to extract patterns from chaos can ignite a chain reaction of triumphant, risk-based decisions. This undeniable truth wields the power to bestow immense advantage or unleash catastrophic consequences.

Tragically, most of the population has squandered vast portions of their lives locked in a relentless game against a cunning few who mastered the art of probability and chance. Unbeknownst to you, you were perpetually ensnared in this competition, pitted against these individuals. They wielded an insurmountable advantage – a treasure trove of truths and insights hidden from your grasp. Did the thought ever cross your mind that your adversaries were armed with a profound understanding that forever eluded you?

To my naive and seasoned corporate executive comrades, those who arrogantly believe they have unlocked all the secrets of life, there is always room for growth. Oh yes, you fierce predators who claw your way to the summit, sacrificing your very essence for the hollow rewards of corporate conquests, battling the sneering intellect and flagrant ignorance of board members, enduring soul-crushing encounters with clueless Wall Street analysts and consultants, and driving yourself to the very edge with relentless 60-hour work weeks – heed my words: my gambling truths are anything but trivial and may carry a gravity you can scarcely fathom.

To my steadfast blue-collar comrades, who might still be grinding away in the twilight of your careers, I present my raw gambling truths as a beacon of hope. Buried within the high-stakes realm of betting and daring risk lies a treasure trove of wisdom potent enough to revolutionize your existence. This profound “body of knowledge” from gambling is infinitely more powerful and transformative than any mundane financial planning course you might be contemplating. So, before you cast it aside as trivial or insignificant, shatter the barriers of doubt and embrace the possibilities that can propel you toward a future ablaze with promise.

Regardless of how brilliant or highly educated you consider yourself, if you fail to grasp that each moment is a high-stakes gamble, you’ll remain oblivious to the razor-sharp skills and profound insights essential for triumph in the ruthless world of high-stakes gambling. Your towering IQ and prestigious degrees won’t shield you from the unforgiving truths of this cutthroat arena. Here, money, power, and adrenaline ignite a relentless fire, and unless you’re prepared to embrace risk and perpetually evolve, you’ll be trampled into oblivion by those who have mastered the brutal art of the probability and risk-taking game. In other words, gambling.

More to come in Part 2.

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