Songfacts®:

• Jhené Aiko's songs tend to represent different sides of herself. She told Radio.com that this tune, which was inspired by a real relationship, channels her confident but stubborn side.
• Aiko told Radio.com that the song's video, which finds Aiko being busted for murder, is a metaphor for her "killing those feelings" that she had for her former boyfriend.
• This was released as a single from Aiko's Sail Out EP. She explained to Artist Direct that the title is a play on words. "Obviously, it sounds like 'Sell Out' in terms of money," she said. "I've always been a fan of writing and words. Wordplay is something I've always loved. I love it when things have double meanings. The album is going to be called Sold Out, and the mixtape is called Sailing Souls. Sail Out was a happy medium between the two titles."
  
  "The cover is me walking into this hopeless-looking place," Aiko continued. "Clearly, I don't have on any clothes. I'm just fearless like, "Who cares?" The boat looks abandoned, and it's a scary situation. I'm going into it being free. I feel like that's what sailing out is about. It's going with the wind and trusting that you're going to end up where you're supposed to be."
• This won the Centric Award at the 2014 BET Awards.