After leaving Sony Music, Aiko released her first mixtape Sailing Soul(s) (2011), independently; the mixtape featured appearances from well-known artists and was met with generally positive reviews and was nominated for Best Urban Contemporary Album at the 57th Annual Grammy Awards.

The album features guest appearances from several rappers, such as Kendrick Lamar, Ab-Soul, Childish Gambino and Vince Staples.

The single's artwork and music video was inspired by John Lennon and Yoko Ono’s Bed-Ins for Peace protest against the Vietnam War.

[3] On January 14, 2014, "The Worst" was serviced to rhythmic contemporary radio in the United States as the album's third single, and peaked at number 43 in April, 2014 on the Billboard Hot 100 chart.

[5] In 2011, she released her debut mixtape Sailing Soul(s),[6] which was received well by critics and was certified gold by mixtape-sharing website Datpiff, for downloads of 100,000.

"[8] Aiko revealed that she has signed to Def Jam via her official Twitter account, the tweet consisted of an image of Jhene Akio and No I.D.

[12] In October 2012, after performing at SOB's in New York City, Aiko revealed to The Singers Room that she is recording a project with No I.D.

One day, maybe", she also revealed that American rapper Big Sean and members of the TDE cats (Kendrick Lamar, Schoolboy Q, Ab-Soul, Jay Rock) may make an appearance on "Souled Out".

"[15] Jhené Aiko also stated that she is working on the album everyday either recording or writing, but is taking her time as she doesn't want "to put out some nonsense".

[15] "Comfort Inn Ending (Freestyle),"features "large swaths" and introspective lyrics that mix between rap and jazz-style scat.

[24] In 2012, Aiko was also the opening act on the highly anticipated “Life Is Good/Black Rage” concert tour headlined by fellow American artists, rapper Nas and singer-songwriter Lauryn Hill.

[26] On January 22, 2014 she performed the song at BBC Radio 1's Future Festival in Maida Vale, London along with her band wearing a flowy white dress.

"Bed Peace" featuring Childish Gambino was released as the album's lead single on September 17, 2013.

[3] On January 14, 2014, "The Worst" was serviced to rhythmic contemporary radio in the United States as the album's third single.

[31] On May 2, 2014 "The Worst" rose from three to one on the airplay Mainstream R&B/Hip-Hop, in doing so she became the first female artist to top the chart as a lead with a debut single since Jazmine Sullivan reached the same feat with "Need U Bad" in 2008.

[41] The New York Daily News gave the EP two out of five stars, praising Aiko's vocals calling them a "feathery tone, sky-high pitch and dazed delivery, she floats above the beat, sexy and aloof".

They also compared the album to the work of Kanye West, Kid Cudi, Drake, Future and Frank Ocean.

[44] On June 16, 2016, the album was certified gold by the Recording Industry Association of America (RIAA) for selling over 500,000 copies in the United States.