After a period living in Boulder, Colorado, where he busked and studied the art of songwriting, Picott moved to Nashville, Tennessee in 1994, where he spent a number of years playing local clubs.
After several years of playing local clubs and supporting such acts as Alison Krauss, he released his first album in 2001. As of 2016, he has released ten albums. Picott met Slaid Cleaves on his first day of second grade and the two became lifelong friends and wrote several songs together.
He began to make a name for himself as a songwriter, which grew when he co-wrote a song on Fred Eaglesmith"s album 50 Odd Dollars.
In 1998 he signed a deal with the management company operated by Denise Stiff, who also managed Alison Krauss. He initially worked as the driver of Krauss"s merchandise truck, but was called upon to fill in when an opening act was needed, which led to a series of support slots with Krauss.
Picott finally released his own debut album in 2001. A year later he released the follow-up disc Stray Dogs.
Two years later he released his third disc, Girl from Arkansas.
In 2014, Picott released Hang Your Hopes On A Crooked Nail, which includes the song, "I Might Be Broken Now". Picott said in an interview that the song was co-written with Amanda Shires and is about their breakup as a couple.