S. Holden Jaffe, the artist behind the indie-pop persona Del Water Gap, could’ve been keeping your books if it weren’t for a stroke of luck in 2020.

Right before the lead single from the artist’s self-titled debut album, Ode to a Conversation Stuck In Your Throat, made its way into the world, Jaffe decided to step away from a career in music, something he’d dreamed of since college when he started the first iteration of Del Water Gap. “I quit music during the pandemic,” recalls Jaffe. “I’d been doing Del Water Gap for a few years, and I called a few of my friends and said I was going to go become an accountant.” The singer is kind of joking about the accountant thing but it’s clear that the Brooklyn-based artist found himself at a serious crossroads. When Ode—a melodic tribute to the words that are often left un-said—connected in a big way (the song is currently sitting on 83 million streams on Spotify,) this aspiring rock star turned temporarily aspiring real-job-haver found himself faced with the idea of getting what you want after thinking it was all over. This triumph, and the feelings that came along with it, are chronicled in Jaffe’s sophomore album, I Miss You Already + I Haven’t Left Yet, released last fall.

The 12-track project, which touches on self-discovery, communication, love, and how to exist independently of, yet committed to, another person, is unapologetically honest, both in its indie-alt yearning and admissions of Jaffe’s own struggles to communicate. In conversation, the singer shares his tendencies to rely on indirect forms, like songwriting, to convey his feelings — a habit that originated back in his hometown of Sharon, Connecticut. “I grew up in a very loving household, but a household where things were communicated by inference,” he says. “One of the ways that I communicate with people is sending these little messages out into the world and hoping that someone would hear it.”

Now, as he moves into his thirties, Jaffe is practicing more openness in his life, a shift that can be heard in his music, as well. He believes that when it comes to the best songs he’s ever written, he was simply a conduit for them, an artistic container meant to deliver a message from above, or even better, from his own subconscious. “A lot of my life as a writer is trying to be open,” says the songwriter. “So that when that message arrives, I can be there to receive it.”

Another element in Jaffe’s sonic evolution is working with producer Sammy Witte (credited on both Harry Styles and SZA’s most recent projects). Throughout IMYA + IHLY’s lengthy recording process—spanning nearly a year and a half—the producer challenged Jaffe to think of himself not only as a writer but also as a live vocalist. Accustomed to creating music that skewed more melancholy, this time he let himself blend despondency with danceability. “This was the first time I just let myself make music that you could sort of bop to,” he says with a chuckle. “I think that’s classically been my favorite music—a bit thoughtful and insightful and sad—but disguised as something a little more hype.” Songs that feel ever-so anthemic, but still are tinged with sadness. That is to say, music is meant to be played live. Which is exactly how it has been. “I spent more time on tour than off tour in the last three years,” explains Jaffe. His most recent set of live shows, the North American leg of the IMHA + IHLY tour, put him in over thirty cities in the span of a month and a half. In these sold-out theaters, a conversation, a ceremonial exchange of energies exists between the artist and his growing fanbase. Under the warm glow of his first headlining tour, one thing is strikingly clear: This is way more fun than accounting.

This story appears in the pages of VMAN 52: now available for purchase!

Photography Daniel Sachon

Fashion Soki Mak

Makeup Melissa Rodgers (The Only) using DIOR Forever Foundation

Hair Yiotis Panayiotou using DYSON Haircare

Executive producer Dan Cingari

Photo assistant Ryan Hacket

Stylist assistant Jack Wilson

Location Smashbox Studios