I have worked all winter, I will not fail summer

from Childish Gambino – Freaks and Geeks Lyrics on Rap Genius

Meaning

If you are working non-stop preparing for big things, it’s unlikely you’ll fail when given the opportunity to shine.

Summer is usually when artists go on tour or drop albums, and it is also when large “Summer” blockbuster movies are made. Gambino may be referencing one or all of these facts.

SUMMER FAIL

Also, Gambino’s album Camp was originally meant to come out the summer following the release of this track (but it was delayed until November 2011). He’s basically saying that Camp will not fail and will be awesome.

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