Lyric discussion by spartan0187 

I think it's more about the human spirit and will to endure, and less about the concept of reincarnation.

The song tries to say that even though men die, there are still others with the same attitude and resolve to press on. You might say they each had the same type of spirit (the highway man) in them.

Per the songwriter -

"I didn’t know where the song was going. Then I realized that this guy doesn’t really die in the first verse. He’s reincarnated. I thought, “Where does this soul go?” The verses started to evolve. He becomes a sailor, then a dambuilder. Then the best idea for me was switching the tense into the future and say, “I’ll fly a starship across the universe divide until I reach the other side.” - performingsongwriter.com/jimmy-webb-highwayman/

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