During an interview on WWFX, "100 FM The Pike", Bob Seger said that "Against the Wind" came about from his days as a high-school cross country runner. He described the song as "about trying to move ahead, keeping your sanity and integrity at the same time." The "Janey" Seger references in the opening lyrics of the song refers to Janey Dinsdale, with whom he had a long-term relationship from 1972 until 1983. In Rolling Stone, Seger elaborated on the song's meaning:
Seger later said that the line "Wish I didn't know now what I didn't know then" bothered him for a while, but that everyone he knew loved it, so he left it in. He also said that it has since appeared in several other hits by other artists, so that proved it was an acceptable lyric.
Music critic Maury Dean described the theme as being about aging and dealing with "all the burdens we'll ever have to face." Billboard Magazine described "Against the Wind" as "a midtempo folky tale of young love featuring pretty piano backing."
Rolling Stone Magazine critic Dave Marsh stated in his review of the Against the Wind album that none of the ballads (including the title track) contained any memorable lines, but he later amended that to acknowledge that the lines "Well, those drifter's days are past me now/I've so much more to think about/Deadlines and commitments/What to leave in/What to leave out" are not only memorable but also haunting in the way Seger "haltingly expresses his indecisiveness."