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I don't remember being beaten in a game of chess with family or friends. I'm sure I have been, I just don't remember. In that circle, I was pretty good. But, when it comes to playing with serious players, I wasn't very good at chess at all. I suspect that's why I started directing chess tournaments.
I got into it head first, by not only directing, but organizing a tournament. In many cases, organizing and directing comes as a package deal, making site accomodations, preparing and mailing flyers, forms for directing, answering calls. Lots of long nights of preparation.
When I got interested and involved with disc golf, it wasn't long before I started thinking about organizing tournaments there as well. I started by directing small one-day events. Then I organized/directed the East Texas Open and players filled the field. I had even better results the second and third year when it was renamed the Paul Giles Memorial.
Now, I'm playing Scrabble®, and have already been certified as a tournament director, though I haven't started anything there yet.