The song was also recorded recently (beautifully, in my opinion) by Gordon Bok, Ed Trickett and Ann Mayo Muir on their CD, Harbors of Home. Gordon explains that it is a lament by a man whose life is on the road (hobo, swagman, etc.) for those of that group who leave for a more settled life. I'd vote for Alan's interpretation, in that it's a life not chosen by many, and not for those who are driven to "win"...whatever that may mean.

Aloha,
Mark