Reach for the stars so if you fall, you land on a cloud

from Kanye West (Ft. Chris Martin) – Homecoming Lyrics on Rap Genius

Meaning

If you fail trying to shoot extremely high, at least you are already relatively high.

It also works as an analogy for how rappers move to LA or New York (the stars) but Ye will always be welcomed in Chicago (it’s the Windy City because it’s in the clouds).

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