[1][2][3] The album was recorded after Lally had moved to Italy, where he met Abela, whom he described as a multi-instrumentalist who can "play music on whatever is in front of her," and Tomasi, "a free jazz kind of drummer.

[4] Regarding the music, he noted that the "record comes out of my own head more than the other ones,"[5] and stated that, whereas on the two previous albums he attempted to "creat[e] a skeleton... an atmosphere or texture" that he would use to guide the musicians, on Why Should I Get Used to It, he "began really trying to flesh out the songs and get them down as demos" prior to rehearsals.

[6] In a review for PopMatters, Corey Beasley described the album as "a cohesive and layered statement, and a successful one," stating that it "sees [Lally] refining his melodic chops and exploring new textures in his gentle, clear voice," and noting his willingness to "experiment with song structures, restless, soft-loud, balancing introspection with forcefulness.

's Vish Khanna stated that the album "features some of the richest grooves and startling playing of any record [Lally's] been a part of," and called it his "finest post-Fugazi work.

"[11] Jason Morton of The Skinny wrote: "while Lally's plaintive vocals might not purvey the same passion as his former bandmates, this LP should satiate the appetites of Fugazi fans, as well as people who like challenging music that doesn't sacrifice melody to push the envelope.