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Career Advice:
Real Winners Know How to Lose

by Ramon Greenwood

The idea of winning is at the very heart of the American work ethic. The gospel of our culture tells us winning is not just the best thing, it is the only thing.

But real winners in the world of work know they can't win them all, nor should they. They have mastered the art of losing, strategically, in their career relationships.

If we insist on winning every single point, we set up unnecessary opposition. Let's face it, nobody likes anyone who always wins.

Fact is, it is not necessary to win every point. It is a very rare situation that has only one right answer. One instance would be in disarming a live bomb. Another would be brain surgery. Otherwise, several acceptable options usually exist.

Winning is not a zero sum matter. There does not have to be a loser for every winner. If we win, it is just common sense to make sure others feel they won, too.

Unless we are absolutely sure we have the only correct answer, or that our organization will be materially injured if we don't prevail, it is wise to let associates win a few. The abilities and morale of the entire team will be improved.

But when common sense and facts say ours is clearly the best, or only acceptable solution, we should fight for it with tooth and claw.

No One Wins All The Time
Anyway, we can't win all of the time, even if we try. We cannot play and we cannot win without taking some risks; and we cannot take some risks without losing some of the time. We just need to be sure we win enough of the big ones.

Thomas Edison recorded some 25,000 failures in his attempt to invent a storage battery. "Those were not failures," he said. "I learned 24,999 ways not to make a battery."

R. H. Macy failed seven times before his first store caught on. Babe Ruth struck out 1,330 times, but he also hit 714 home runs.

Dr. Harry Levenson, noted psychologist and adviser to management, says that a key characteristic of successful managers is the willingness to take big risks. "Not crazy risks, but big risks," he says. "They are willing to endure the distress of fear and uncertainty until the results are known. They stick with their decisions even when there are some downers before their ideas begin to pay off."

If we truly want to build a successful career, and we work in an organization that demands that we always be right, we are in trouble. Such an environment will not allow us room to grow and achieve success. We will either be stifled or we will be in trouble for trying new ideas and for making the inevitable mistakes that go with them. We should get out as fast as we can, unless we want to live in a suffocating bureaucracy.

Healthy, growing organizations expect their people to make some mistakes. But not too many!

Winners take common sense risks. They are ready to lose some of the time in order to be a big winner in the end. They know how to lose strategically.

Ramon Greenwood is Senior Career Counselor for He is a former Senior Vice President at American Express, a published author and syndicated columnist, a professional director and an entrepreneur.

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