Produced primarily by band members Black Thought, Questlove, Dice Raw, and Rick Friedrich, How I Got Over features a subtle, somber sound and lyrics concerning themes of self-determination, existentialism, and African-American middle-class angst.

[7] It was recorded in sessions at several Philadelphia studios—A House Called Quest, Fruity Loops, The Boom Room, and The Studio—and at MSR Studios in New York City.

[8] On June 23, 2009, Billboard reported: "Among the tracks expected to make the cut are 'Walk Alone,' the vintage R&B-leaning 'Make a Move,' 'The Day' featuring Icelandic vocalist Patty Crash and a cover of Frank Zappa's instrumental classic 'Peaches en Regalia.'

'How I Got Over' is also expected to include a version of Cody Chesnutt's 'Serve This Royalty;' the singer-songwriter rose to fame in 2002 when the Roots re-recorded his song 'The Seed' for their album 'Phrenology'".

[36] AllMusic's Andy Kellman described the album as "deeply planted in realism ... gracefully and cleverly sequenced",[27] while Rolling Stone critic Nathan Brackett highlighted The Roots' incorporation of indie rock elements into an "in the pocket" sound.

[32] Pitchfork's Nate Patrin deemed How I Got Over "a particularly efficient album ... the Roots' shortest (a lean 42 and a half minutes), one of their most lyrically straightforward, and a work of strong stylistic cohesion".

[4] James Shahan from URB found it "dark and tragic in places, but also enlightening and empowering",[37] and Spin journalist Charles Aaron said "you'd have to rewind early-'90s Scarface or Wu-Tang for such convincingly cold-eyed hip-hop existentialism".

[1] Eric Henderson was less enthusiastic in Slant Magazine, finding the lyrics inconsistent and "mildly self-delusional" while calling the album "stylistically the most inert, contemplative, offputtingly soft music they've possibly ever released".