The Limits of Planning

July 27, 2015

Like many Michiganders, I took a summer vacation. And as I always do, I planned the trip thoroughly ... from flights to sights to accommodations to restaurants, but still leaving a few details to spontaneity and serendipity.

This summer's trip was to Newfoundland, where winter was very grudgingly giving up its grip. Everything about summer was slow in coming, and the thousands-of-years-in-the-making icebergs that had drifted down from Greenland were several weeks later than usual to disappear off Newfoundland's coast.

It was a trip that once again reminded me of the limits of planning.

Understand, I am an ardent advocate of planning. First, I am my mother's son who would often say that "Happiness is having a plan." Second, I'm so obsessed with planning that I committed to writing two decades ago what should happen when I die, which actuarial tables inform me should be even longer than two decades in the future. 

But once again, all my planning for this vacation failed to provide its best moments. The best accommodation was the one I did not book in advance; the best restaurant was the one I had not heard of before we departed from Michigan; the best iceberg adventure was the one we had on our own after taking a wrong turn, not the commercial tours we took in groups. 

Planning is a necessary part of leadership and it is essential for the success of any enterprise. But so is staying open to hunches, going with your gut and learning from mistakes. This often makes for the most memorable vacations as well as the most meaningful vocations.

Winning

December 26, 2012

If you and I were playing a game of, let’s say, a game of tennis, and I don’t try to win, and you defeat me, I’ve cheapened your victory.  And in cheapening your victory, I’ve been a poor sport.

Trying to win is a good thing.  Trying to win is a goal of school sports.  Trying in the best way, that is:  within the rules, with all our effort, and with grace, regardless of the outcome.

The most satisfying victory we can have in sports is defeating our best opponent on our opponent’s best day.

The least satisfying victory is against a weak opponent, or as a result of an opponent’s mistake, or an official’s bad call, or – worst of all – by our own cheating.

You want your best opponent on their best day.  You feel the best when you defeat the best, playing their best.

That’s ecstasy in sports.  There is no better feeling in sports.

Don’t mistake anything I ever write to mean I don’t care about winning.  I really do.  And I care that it has real value.