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How to Win

The Deal You Make Every Day

On this date 92 years ago, the Boston Red Sox sent the contract of Babe Ruth to the New York Yankees for $100,000.

Boston owner Harry Frazee needed money to get out of debt. So he made the deal.

We all know how the deal turned out. Ruth became a Hall of Famer, the Yankees became baseball’s most successful franchise, and the Red Sox did not win another World Series until 2004. It was a really bad deal, the kind that keeps the return desk busy on the day after Christmas.

It’s easy to criticize Frazee for the deal, but the fact is that everyone — you, me, everyone — makes a deal every day. And that deal often turns out much worse than Frazee’s deal did.

The deal we all make every day is the exchange of our time for some return. Sometimes the return is relaxation, sometimes it’s amusement. The most successful people invest their time in creating skill or building something worthwhile.

American writer Ambrose Bierce defines a day as “a period of twenty-four hours, mostly misspent.”

John Wooden said, “If you don’t have time to do it right, when will you have time to do it over?”

One way to judge how well you’ve spent a day is to take the Pillow Test. When you go to bed at night, will you say to yourself, “I’m glad I did,” or “I wish I had.”

People who say “I’m glad I did” are making the correct deal. Those who say “I wish I had” are like Harry Frazee.

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TotalGamePlan offers Winner’s Workshops for schools, sports teams and businesses. The emphasis is on motivation, skill-building and teamwork. To bring a Winner’s Workshop to your group, just email coachtully@totalgameplan.com or call (973) 800-5836.


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