Born in Pittsburgh to two blind parents, both of whom were living-room musicians, he began playing piano and trombone in elementary school and taught himself guitar as a junior-high student. Over time, he also learned to play banjo, melodica, ukulele, and mandolin. While pursuing a master's degree at Geneva College, Fitzsimmons began tracking some of his songs on home recording equipment. These self-produced recordings were compiled together and released as 2005's Until When We Are Ghosts, a strong debut album that appeared during Fitzsimmons' time working as a mental health therapist.

Over time, Fitzsimmons began to attract a following on MySpace. Of course, it didn't hurt that his songs started showing up on various television soundtracks, too, including Grey's Anatomy, General Hospital, Life of Ryan, and Army Wives. A second self-produced album, Goodnight, appeared in 2006, influenced heavily by his parents' divorce during his childhood. By this point, Fitzsimmons had settled on a distinct sound: a gentle mixture of folk-rock and electronica applied to carefully written (and often autobiographical) songs that, at their best, delivered a quiet emotional punch. He carried the theme of divorce into his first official studio album, 2008's The Sparrow and the Crow, which dealt with a recent split with his wife. Released in 2010, Derivatives lightened things up by focusing on electronica remixes of his past work (as well as a cover of Katy Perry's "I Kissed a Girl"), and 2011's Gold in the Shadow found Fitzsimmons confronting his demons with help from guest artists like Julia Stone. Lions, produced by Death Cab for Cutie's Chris Walla, arrived early in 2014, followed by the mini-LP Pittsburgh in 2015. ~ Steve Leggett & Andrew Leahey