Take Jack Horton, a Portland-based singer-songwriter whose path to folk-Americana included stops at Japanese law school, Tokyo piano bars, corporate boardrooms, and government offices.

His latest EP, “Imperfections,” feels like finding someone’s private journal set to music. And that someone happens to write really, really well.

The five-song collection opens with “Set Me Free,” a piano-driven confession that might surprise anyone expecting typical breakup bitterness. Horton explores something far more complex: the strange gratitude that can emerge from divorce.

His vocals carry weight here, the kind that comes from someone who has genuinely processed pain rather than simply wallowing in it. The track demonstrates how personal transformation often requires letting go of what we thought we wanted most. It’s counterintuitive, like finding relief in a thunderstorm.

Horton’s classical piano training provides the foundation throughout “Imperfections,” but never overwhelms his storytelling.

Each note serves the narrative, creating space for listeners to absorb the emotional complexity he’s presenting. This restraint feels intentional rather than accidental.

The production maintains consistent intimacy, allowing Horton’s voice and piano to remain central while supporting instruments add texture without distraction.

“Never Know Why,” featuring Vesper Stockwell, shifts the EP’s emotional centre entirely. This powerful duet starts bare and builds to a full symphony, showcasing the incredible chemistry between Horton’s gravelly voice and Stockwell’s crystalline clarity.

Their harmonies create something that feels both inevitable and surprising. The song explores love’s inexplicable nature, how the need to be with someone often sidesteps logic entirely.

Stockwell’s voice cuts through like sunlight through rain, while Horton anchors the emotion with his weathered delivery.

The collaboration feels natural, probably because Stockwell is Horton’s partner. But their musical connection transcends personal relationship. They sing like two people who have learned to finish each other’s sentences, then decided to do it in harmony instead.

Horton’s background as an attorney, government official, and tech founder might seem disconnected from his musical pursuits, but these experiences inform his songwriting in subtle ways.

His lyrics demonstrate the precision of someone accustomed to choosing words carefully. There’s legal-brief clarity in how he constructs emotional arguments. Meanwhile, his melodies carry the emotional intelligence of someone who has lived multiple professional lives and found them all wanting in different ways.

The EP includes a reworked version of Jim Croce’s “Operator,” which could have been a misstep. Instead, Horton makes it his own without losing what made the original special.

It’s like watching someone translate poetry between languages while keeping the soul intact. His interpretation feels both respectful and personal, proving his versatility as both musician and storyteller.

“Imperfections” succeeds because Horton refuses to present himself as having figured everything out.

Instead, he offers the ongoing process of figuring things out, complete with false starts, unexpected discoveries, and moments of genuine surprise.

This honesty creates connection with listeners who recognize their own struggles in his songs. It’s the difference between reading someone’s autobiography and overhearing their therapy session.

The production choices feel deliberate throughout. Horton’s classical training supports rather than dominates his folk-Americana sensibilities.

The arrangements build organically, never feeling forced or overproduced. Each track maintains the intimate feel of someone playing piano in their living room, even when full instrumentation enters.

What makes “Imperfections” particularly compelling is how it handles vulnerability. Horton doesn’t weaponize his pain or use it for cheap emotional manipulation.

Instead, he examines it with the curiosity of someone genuinely interested in understanding how things work. The result feels both deeply personal and universally relatable.

The EP’s title proves prophetic. These songs find beauty in life’s rough edges, in the places where things don’t quite fit together perfectly.

Horton has created something that feels both polished and raw, professional and intimate. It’s the kind of music that makes you think about your own imperfections and how they might contain hidden beauty.

“Imperfections” leaves you thinking long after the final notes fade. Horton has crafted a collection that proves the most effective art often emerges from our most vulnerable moments.