If I ain't thinking about cash, nigga
I'm thinking about life
Making a change, no winners do the same shit twice

from Kid Cudi – Rain Lyrics on Rap Genius

Meaning

Cudi realizes that life is all about progression, and making changes, both in life and in music.

In life, he’s tried to make his life better through change by making the decision not to smoke any weed anymore.

In his music, he has tried to stay relevant through changing up his style a lot: from his hard raps in early 2000’s on “Rap Hard”, to his more chill/ depressing even Man on the Moon’s, to his new music, like this, which seems to be more straight raps. Also, he announced via Twitter that there won’t be any expletives on his upcoming album Wizard.

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