Referring to JhenΓ© Aiko's EP "Sail Out", the phrase means to "Be free, go with the wind, like a sailboat."
"It's really important to sail out when it comes to peace... inner peace especially. You can't help anyone else if you don't have it together yourself."
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A guy that's says he's so in love but will catch the wind and leave you high and dry when he's ready
Don't be a Sail Out typa nigga!
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