Barrel Jumping (A Man of Letters) Lyrics

Lyric discussion by SecondFig 

Cover art for Barrel Jumping (A Man of Letters) lyrics by Astronautalis

My favourite song on The Mighty Ocean, I just love how resigned and weary he sounds...

I'm not at all sure, but it sounds like he's describing going over a waterfall in a barrel - as a way out, an end. A love gone wrong that he's escaping...?