Michaelson began writing songs in his mid-20s. Michaelson formed Absentee in 2003, the group releasing three albums between 2003 and 2008. In 2009 he began a side project, recording as Dan Michaelson and The Coastguards, the initial release under this guise being the Saltwater album and "Bust" single, released by Memphis Industries in 2009.
A further album, Shakes, followed in 2010. The band included Henry Spenner (drums - of Fields), Laurie Earle (piano/guitar), Sanjay Mitra (bass guitar), and Horse (pedal steel/guitar).
In November 2011 he released the solo album Sudden Fiction, inspired by time spent in Marfa, Texas, drawing comparisons with Bill Callahan.
Blindspot followed in 2013 and Distance in 2014, released on The state51 Conspiracy. NME describe Distance as 'forlorn Americana to rival The National', awarding the album 8/10.
Michaelson described 2016's Memory as the final part of a trilogy.
In 2017 Michaelson released First Light, working without The Coastguards for the first time since Sudden Fiction.