“Grand strategy is the art of looking beyond the present battle and calculating ahead. Focus on your ultimate goal and plot to reach it.”
- Robert Greene

While most are terrified of losing, I fear winning – winning at the wrong game. Losing carries a sting that encourages learning and subsequent change, but winning reinforces perspective, builds confidence, and emboldens further pursuit. But what if you continue to win at the wrong game? It can take a lifetime (or longer) to realize and correct course.

Winning and losing always comes down to preference. One man’s win is another man’s loss. To that extent, the score of life is extremely personal. The challenge is our comparative nature. Whether we like it or not, we’re constantly being judged, with money, fame, and power as the dominant metrics for most. It often proves challenging not to adopt a similar viewpoint, or at least occasionally take a peek at the world’s scorecard.

But as the old adage says, “Where there’s smoke, there’s fire.” Those metrics often do tell us something. The wealthy, powerful, and famous are, on average, more remarkable than the general population. The problem lies with the individual. Those attributes are merely the byproducts of some combination of luck and value creation. In the short term, true performance is always obscured and metrics are easily faked, making meaningful progress difficult to measure. How much of last year’s returns were the result of good fortune? Who knows. How much credit is your neighbor consuming with the new Beemer and designer clothes? Only time will tell.

Truly winning starts with establishing the right goals (for you) and adopting a long time horizon. It takes both, each of which is incredibly challenging, to produce a positive outcome.

Is “getting healthy” about losing the most weight? Is “being wealthy” about having assets or cash flow, or something else? Over what timeframe do you measure returns? In the short term, couldn’t the winning company have the most financial, cultural, or code debt?

Be cautious in admiration and courageous in self-reflection. In 2008 the three most admired athletes were Tiger Woods, Lance Armstrong and Oscar Pistorius.

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