I would very much like to be a gym leader, I would have come from a long line of circus preformers who preformed with Pokemon. My greatgrandpa decided to end the carefree life of a circus and start a gym. This gym would be handed down to my mother, and then to me.
My Pokemon would be ciruc-trained like Ursaring, the Dancing Bear and so on. I would have lost my feel for the life of a gym leader somewhere in my early adult hood, being bored with it all. A pluck young trainer would challange me, I'd kick their butt and they'd challange me again. Their determination and well worded speech would make me snap to my sense, and then I would join them.
We'd have madcap adventures (Join some contests, stop an evil organization) for a while (At least a season or two), and then I'd go back to my Gym where there is tumoil. Grasp it by the horns and make it better.
I'd be dressed outragously at all times, never know where I'm going and eat all the food while we travel.
^_^