Why Me? (part 2)

My research into my own seemingly “bad” luck convinced me that the age-old quote attributed to the Roman philosopher Seneca—“Luck is what happens when preparation meets opportunity”—was not the whole story. There was something else that contributed to manifesting good fortune. Sure, solid preparation (like training to run a marathon) is a clear improvement over a lack thereof, and yes, opportunity (like entering or qualifying to run in a race) is the most obvious contributing factor. But somewhere between those two, I believed, was yet another element, or perhaps another kind of preparation. Certainly, there were also a million different things that could interfere to derail the “preparation + opportunity” scenario. I was convinced that a significant amount of luck relied on one’s mindset toward, and flexibility in relation to, all those elements that remain outside our direct control. So, I looked for that “something else,” and piece by piece, put it together. As I assembled its constituent parts into a formula, I became certain that applying that formula—in our personal lives, in the business world, wherever—nearly guaranteed success.

Of course, I didn’t just think this through. I set out to prove it so.

I had learned some things from my formative experiences. Seven years of Olympic sailing campaigns, culminating in 1988, taught me the “ten-thousand-hours rule:” try at something long enough and you can succeed. But finishing fourth in the Olympic trials was also a lesson: ten thousand hours alone is insufficient.

Racing on the McGill University alpine skiing team taught me that genetics were to be respected: my five-foot-eight frame and 145 pounds made me competitive in slalom, but I simply was not big enough to compete in the high-speed thrill event I loved most: the giant slalom. Ten thousand hours of practice got me a long way, but not to the ultimate inner satisfaction of proving that I could accomplish anything I wanted.

After college, I joined my first company in Toronto, Canada. My inspirational CEO, Michael, and lifelong friend and mentor, Neil, were instrumental in challenging me and giving me all the rope I desired. Rather than hanging myself with it, I pulled myself up, and with their support, earned an incredible opportunity to build a new venture in balmy southern Florida. That venture was supremely successful, and I had that first sweet taste of success that I had craved since being the kid who was bullied every day on his way home from school. My venture was a success, and I was cash rich.

I lived on a beach road and learned to surf. I had the adoration of beautiful women and drove a gorgeous convertible. I felt like I was living my dream.

Then, in skiing terms—I got out over my tips.

We sold the company, and I was arrogant enough then to think that I could go it alone. The result: I over-extended myself and completely squandered the proceeds. Less than one year later, at age twenty-five, I had almost zero financial net worth.

For a year I bounced along, trying to find direction. I was consumed figuring out what had worked and what hadn’t. I reflected on all the times in my life when I was “at my best,” and looked at them alongside those when I was “at my worst.” What emerged was a clear set of attitudes and behaviors that I had practiced when at my best and had neglected—even worse, quite consciously ignored—when at my worst.

Reflecting on my own successes and failures, I generated a set of “principles” that I wrote out by hand. That list became a sort of hypothesis upon which the next twenty years of my life, and ultimately this book, would be built. Starting that year and then every January thereafter (on my birthday), I would review the year that had just passed and then write a plan for the year ahead the baseline and compass for which were these very principles.

My first accounting of my life against these principles was in 1998. I was inspired by the resulting vision as much as by the deep sense of humility they engendered, so I made a decision that—much as it may have looked otherwise to others—made total sense to me. I wanted a fresh start for my new life. I loved the beach, hated paying taxes, but wanted to be close enough to fly only a few hours to see my family. So, I sold my last asset—my TV—and purchased a one-way plane ticket to Bermuda.

(cont’d)…

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