During a break touring to support his self-titled debut album, McMahon wrote new material with Gregg Wattenberg and Derek Fuhrmann.

[5] In August 2015, McMahon revealed had been writing a lot of material for his next album and attempting to build a strong group of songs that he could work on following the touring cycle.

[9] Later that month, and into January 2016, McMahon's band Jack's Mannequin reformed for an anniversary tour to support their debut album Everything in Transit (2005).

[12] After learning that a lot of New York-based writers/producers had migrated to Los Angeles,[6] and having had a positive experience writing "Fire Escape", he relocated to New York City.

[18] The city's bars remained open until 4:00 am, which "got the best of [McMahon] him", and he subsequently returned home to California to continue working on the album.

[20] "Brooklyn, You're Killing Me" and "Island Radio" were recorded at Studio America in Los Angeles, California, with English acting as engineer.

"So Close", "Fire Escape", "Dead Man's Dollar", "Shot Out of a Cannon", "Walking in My Sleep", "Love and Great Buildings" and "Birthday Song" were recorded at Arcade Studios in New York City, with engineer Mike Adubato.

"Don't Speak for Me (True)" was recorded at Arcade, Play Beats Studios in London, England, and Infrasonic Sound in Los Angeles, with engineers Jerome Williams and Suzy Shinn.

[21] An underlying theme of the album was McMahon reconciling with his tendency to gravitate towards late nights and drinking heavily.

[26][27] While in New York City, he spent many nights in festival tents listening to dance music, namely FKA Twigs, Lido, Sylvan Esso and Atlas Genius.

[12] "Zombie Intro" is a short 27-second long track[28] that consists of city noise,[29] passing trains and chatter from a New York subway.

Here, he encountered "the acrobat, the banker, the oxblood friend; these larger than life characters ... that lead me through the boroughs, bodegas, bars and subway stations," which he referenced in "Fire Escape".

[34] The track has soft verses with strong chorus sections[28] that incorporate chanting in the same vein as the band Walk the Moon.

[35] "Dead Man's Dollar", one of the first songs written for the album,[36] talks about working long days to provide for one's family.

[37] It combines the lyric fragility of "Don't Speak for Me (True)" with the pop tendencies of "So Close" and "Fire Escape", starting with a quiet piano before eventually building by adding guitar and extra backing vocals.

McMahon explained: "I am someone who craves constant motion, but once plane rides and hotel nights accumulate there is a sense that the world has shifted in some imperceivable way.

[6] Directed by Jon Morris and Michael McQuilken,[41] it features two inflatable dancers falling in love in different locations around Brooklyn.

[50] The Japanese edition, released on June 7, features the demos "Throwing Punches" and "Rich Kids with Summer Jobs" as bonus tracks.

[37] The Hoya's Rachel Linton said the album was "powered by McMahon’s strong sense of metaphor-based lyricism and catchy rhythms", showcasing his "increased musical ambition".

[28] Substream Magazine reviewer Jessica Klinner found it full of "gut-punching, tear-jerking lyrical content and catchy alt-pop melodies".

"[56] Sputnikmusic staff member SowingSeason said it was McMahon's "first album since Everything In Transit that simply explodes with life and energy; whether it’s the enormous pop hooks, the dynamically interwoven verses, or the optimistic lyrics".

[23] Annie Zaleksi of Alternative Press said that "[n]ot only does the album overflow with stick-in-your-head hooks, but it also boasts contemporary production, from sleek digital programming to airy synthesizers, to go along with more traditional band-based instrumentation".

[30] AllMusic reviewer Stephen Thomas Erlewine wrote McMahon was "dedicated to carefully constructed melodies and earnest emotional blood-spilling".

Club's Chris Mincher said that while McMahon "fully throws himself at reminiscence and reflection", he "allows his seasoned songwriting to fall onto an adult-alternative treadmill of formulaic chord-plunking and bombastic choruses that's big on impact and short on invention".

[27] Melodic reviewer Johan Wippsson said it was full of "clever pop in a slightly electronic packaging", following "the same path [as the debut]".

[54] Rolling Stone Australia reviewer Rod Yates said it "feels interchangeable with much of what's currently on pop radio, with McMahon's personality and soul smothered under a mass of shiny production techniques".