[3] His latest works have been released by Righteous Babe Records (album) and Write Bloody Publishing (books).
In 2001, he left his position as an executive assistant for a biomedical firm[5] in Gig Harbor, Washington, sold or gave away everything he owned, and moved into a Honda Civic to tour North American poetry venues.
A Choir of Honest Killers (2019, Write Bloody Publishing), Wakefield's first book of new work in eight years,[12] will be released October 15, 2019.
Wakefield and Stephen Snook have published an entertaining table book on chicken rearing: Henhouse: The International Book for Chickens and Their Lovers (2012, Write Bloody Publishing) ISBN 978-1-938912-05-4 Wakefield has also released three full-length spoken word albums with producer Jon Berardi: A Stretch of Presence (1999) (co-produced with Levi Lyman), Run On Anything (2006) which was released by Strange Famous Records,[13] and Live at the Typer Cannon Grand (2009) which was released by Ani DiFranco's Righteous Babe Records.
"[5] The album contains recordings of live performances, including several from Wakefield's numerous times opening for DiFranco on her tour, as well as one studio-produced track.
In 2007, Wakefield began touring annually with Derrick C. Brown and Anis Mojgani, calling their group “The Poetry Revival.” Each year, the group invited other popular performance poets and musicians to join them for certain legs of the tour, and altered the name slightly to reflect the changing line-up.
Wakefield has had a profound impact on the contemporary Poetry Slam movement, both in his performance and writing style as well as how he has conducted his career.
She wrote, ...[Wakefield] sold everything he owned and toured the country, living out of his car when he wasn't crashing on couches.