LOOK OUT, WORLD: Simmons dreams in melody, gets drunk on vintage pop, and counters adversity with pretty, harmonic couplets.

So forget that I’m writing from a college-kid bivouac. The context for Simmons’s Farewell, My Sweet Alibi (Kool Kat Musik) isn’t civic or temporal; it’s classic and archival. Elvis Costello’s plaintive phrasing. Moody Blues–ish mellotron. Harry Nilsson’s bouncy melancholy. Ten songs of late-’60s incandescence that are written, produced, and recorded by a Cambridge-based 30-year-old who dreams in melody, gets drunk on vintage pop, and counters adversity with pretty, harmonic couplets. “Sad times are coming up,” Simmons augurs over a Hammond organ. To which he responds blithely, “Na-na nah-nah.”

Also, blog dudes, you wouldn’t be latching onto a regional trend: Simmons is virtually unknown in these parts. Farewell, My Sweet Alibi may be his third full-length release, but his face hasn’t been piled up by bar entrances on local rock rags, and neither has his name been stamped all over club listings. His most recognizable musical role is probably as the Greg Brady–haired guy who spent years behind the Planet Records counter in Harvard Square. (He now has a “regular day job” in the Back Bay.)

Of course, until last Saturday at T.T. the Bear’s, he hadn’t performed for a live audience since 2004 — and that was a “loose, sloppy, drunk” night in which he covered Neil Young’s Tonight’s the Night with his former backing band, the Symptoms. Some musicians write songs as an excuse to tour; Simmons, who’ll be at the Middle East upstairs this Wednesday, talks about dragging out his equipment as an unfortunate necessity, a burden to endure so strangers will get to hear his compulsively crafted record. “I look at that whole experience like it’s time-consuming,” he tells me at the Other Side Café. “I just don’t enjoy it as much as recording and writing.” Shows demand compromise, especially for a songwriter who’s credited with playing seven or eight different instruments on his most recent tracks. “There’s so much going on [in the record] that I’m not sure how we’ll pull it off. We can’t have people playing with their feet.”

Farewell, My Sweet Alibi’s opener, “Half Dollar,” begins with violas. Hopeful strings. Ebullient strings that make gracefully bold entrances like the first actresses on stage in a Broadway musical, handpicked for their lovely confidence. Then the strings coax in the drums, the handclaps, the vocals, the pianos, and the other instruments that are gamboling around the song’s orchestral layers. There’s a banjo mixed so low, it tickles. A bass quietly throbbing. Then those strings again, nudging away the jaded reluctance to acknowledge that this is radiance, this is joy, this is a timeless feel-good pop tune. “All my free time’s for sale,” Simmons offers, then beckoning again and again, “C’mon and show how it’s done.”

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He doesn’t need the guidance. Farewell, My Sweet Alibi is his first product of ProTools hermitage, a daedal composition he spent months obsessively tinkering with in his pajamas. “Feeling comfortable at home, not watching the clock, just being able to be totally relaxed — I think allowed me to get exactly what I wanted.” He says he mostly writes in flashes on the bus, on the train, on the street. In this case, he knew exactly how he wanted to embellish those epiphanies, which is why he stopped collaborating with the Symptoms, who’d been on his last record, Almost . . . All the Way . . . Down (2003). “I just had a really clear idea of what I wanted and that didn’t leave much room for the two other people. I didn’t want it to sound terribly ‘singer-songwriter’ — I wanted to avoid sounding like a folked-up sap.”

“Folked-up sap” implies histrionic treacle; Simmons’s songs are emotive but in that universal pop sense. Love is a wager (“Lovely Liar”); hearts teeter-totter like playground equipment ( “See Saw Heart”), and they come with damage-ready diagrams (“Blueprints,” which casts heartbreak in architectural terms against a 12-string guitar jangle à la the Byrds). “Paperweight” is a wistful, airy, carpe-diem-reverie-turned-stationery-supply metaphor over an e-bow shudder. But those themes say more about the record’s mood than its mission: at most points, the lyrical symbols are secondary to the layered song structures. In “Tall Tales,” Simmons toys with shifting tempi, segueing from a percussive trot to a church-organ drone to a trilling tone that seems squeezed out of a dolphin’s blowhole. Such abrupt transitions, he explains, “were a big thing for me — like a Brian Wilson Smile thing — it’s all fragmented. It kind of seems like, ‘What the hell just happened?’ Like somebody bumped the machine while it was recording.”

Farewell’s dénouement is the title track, in which Simmons reckons with turning 30, dolefully serenading his 20s as if they were victims of a forced break-up. That goodbye is the finale because, “If I lose my arms in a car accident or something like that, I’ll be happy that I made this record.”

JEFFREY SIMMONS + PINOCCHIO SYNDROME | July 5 | Middle East upstairs, 472 Mass Ave, Cambridge | 18-plus | $8 | 617.864.EAST