Some people have creative genius beyond what any of us could comprehend while skiing. Some people attempt moving chairlift to rail transitions while skiing. They aren’t usually the same people. Fortunately Hank was wearing a helmet and didn’t seem to wind up with any major injuries. Still, this probably wasn’t the best decision.
I’m no physicist, but wouldn’t he need to be moving in the desired direction of travel for this to really work out? Even if he somehow managed to land on the rail, would he be able to get moving downwards? Maybe he knew the outcome all along, maybe he didn’t.