Taken from this page:

This song is very powerful and has great meaning. Undoubtedly, noone can really understand the true underlying meaning better than the writer, Kris Kristofferson. In an interview he gave with The Dallas Morning News in 1990, he expressed deep emotion when talking about the song. In the interview he stated, "I was writing about the irony of personal freedom. It's like a two-edges sword. The freest you are, the loneliest you are. But it's something that I need."