I worked as a dockboy at a resort a few year ago.

One day my dockboy intuition told me there was trouble. Someone had unhitched their boat from the trailer before rolling it down the landing (our landing is about 35 degrees steep). Sure enough, his boat started rolling off the trailer before it was in the water. The guy floored his truck so his boat would land in the water and not on the cement landing, but, as a result, his boat was now floating away from the shore with no dock-line.

Our main dock is parallel to the shore near the landing. When I noticed that the boat was floating away I figured I would just run down the dock, jump in, and drive it back to the dock. It looked to be only a few feet away from the opposite side of the dock I was on. So I started running down the dock to jump in and when I got near the end of the dock I noticed it was actually about 8 - 10 feet away. I was going too fast to stop and try again, but I wasn't fast enough to make it either so I just had to go for it. I leaped far enough to get my feet onto the side of the boat, but didn't have enough momentum to actually step into the boat so I just fell back into the water.

All I could do was swim the boat back to the dock while everyone in the boathouse and on the shore were laughing their asses off. I destroyed my cellphone which was in my pocket and soaked everything in my wallet and the tip money I had in my pockets. The idiot whose boat I swam back didn't even tip me OR thank me.

It was a shitty day to begin with, but at least everyone got a good laugh at my expense.