In 2002, my older brother tried something similar. First, he was going to attpempt to do this exact same thing, but instead of a diving board he was using the roof of our back porch. Fortunately, he was smart enough to realize that the pool was a good five feet away from the edge of the roof, so leaning off would probably result in him faceplanting into the pool deck.

So instead, he decided to put the kayak in the pool (upside down), and jump onto it from the roof like a cowboy would jump onto his horse in a cheesy Western flick. I happened to be watching from the kitchen as I saw his body fall from the roof, land with an excruciating finality, legs wide open, on the kayak, and comically slide off the side into the water.

Nearly a decade later, he still doesn't know why he did it.