The song "Man Of Constant Sorrow" is not originally by Waylon Jennings, but rather a traditional folk song that has been covered by various artists including Jennings. It gained popularity through the soundtrack of the film "O Brother, Where Art Thou?" In this song, the narrator describes himself as a man who has experienced constant trouble throughout his life. He is familiar with misery and struggles, and he decides to say goodbye and leave tomorrow, vowing not to return the same way. The lyrics suggest that the constant sorrow and difficulties have become a part of the narrator's life, and he hopes that by leaving, he can find some relief for his troubled mind. He acknowledges that he cannot meet the expectations placed upon him and expresses the desire to find satisfaction elsewhere. The repeated chorus emphasizes his determination to move on and leave the troubles behind. Overall, the song conveys a sense of resignation and yearning for a better life, away from the constant tribulations. It speaks to the universal human experience of facing challenges and seeking solace and redemption.