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LESSON: If we have the foresight to arrange our lives today in preparation for not only continued success but also in anticipation for extreme adversity that will likely appear, our chances of survival will increase dramatically. If I had practiced greater humility in my material acquisitions, as well as my lifestyle and personal choices, I would have likely fared much better in my challenges with regulators, shareholders, and jurors.


The below lesson is an excerpt from my recently released Amazon #1 Best Seller, When Not If: A CEO's Guide to Overcoming Adversity, Forbes Books. 


Leaders, I previously told you how your success will be used against you by regulators and prosecutors, but more importantly it was my fault not to practice greater humility to begin with.


When after considerable struggles, one becomes fortunate to achieve financial and career success, practicing humility becomes almost a full-time job. With each year of ever-expanding achievement, I increasingly misplaced my priorities. If humility means not thinking less of yourself but thinking of yourself less often, I definitely lost my way. My attention increasingly focused on the things that money could buy: fine suits, fine cars, private jet travel, and the Chihuly chandelier for the foyer. And, in turn, I, ever so slowly, stopped prioritizing beating everyone to the office and showing up at the 6 a.m. workouts that made me so productive.


Now, let me pause here and stress I do not buy into the crowd that says you have to drive a Buick (sorry, Tiger!) and buy cheap suits, so your clients don’t think you make too much money providing their services.


On the contrary, I subscribe 100 percent to the school of thought that successful people want to work with successful people. As long as you join those circles with the right attitude and balance of values, it can be an effective business strategy.


It is easy for everyone to believe the Wolf of Wall Street stereotype because it feeds human insecurities and our excuse-driven culture. Yet, the great majority of successful, and wealthy, people I have come to know in my own success have been kind, generous, and humble. Most acquired their wealth as first-generation entrepreneurs and honored their humble beginnings by not flaunting their success.


But I kept slipping, and I served up so many symbols and narratives my detractors could use against me, in business as well as the legal battle I was too blind to see waiting to ambush me.


My purchase of a Bentley automobile was another way I signaled my success. Little did I know it also signaled my obliviousness to how it looked and how it would be used against me. Sarah, a friend and long-term country club member, was not happy with my conspicuous consumption. She pulled me aside, like the principal pulling a student by the ear, and whispered, “Are you crazy buying a brand-new Bentley? In Newport News, Virginia?!”


“But it’s not the big fancy model!” I lamely protested.


“You just don’t get it,” she said. “They will crucify you for this.” And she was right.


At the time, though, the exchange seemed ludicrous to me. I ordered another martini from the bartender, Bob, and quickly dismissed the conversation, like I dismissed most conversations that threatened to confront me with reality. As I mentioned earlier, the Bentley consumed 20-minutes of Judge Doumar’s sentencing soliloquy.


I should have been smarter.  I’m not sure what the right balance is here of enjoying a good life versus serving up ammunition to your detractors, but I do know I could have made 1,000 better decisions.  I lay out my examples to help you think about what is right for you.


Do you wish to rise? Begin by descending. You plan a tower that will pierce the clouds?

Lay first the foundation of humility.

—    Saint Augustine


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