Dessa went to Southwest High School, graduating from the IB Diploma Programme in 1999. She attended the University of Minnesota, where she earned a B.A. in philosophy. Before becoming an artist full-time, she worked as a technical writer for a medical manufacturer.
Initially drawn to their raw aesthetics and unique sound, Dessa forged a friendship with Doomtree. Soon after, she started dating P.O.S. Though they eventually ended their relationship, she was asked nonetheless to join the crew, and did so. Since 2005, Dessa has appeared on numerous Doomtree albums, as well as on the other members' solo albums. She is also the CEO of Doomtree.
Dessa's debut solo EP, False Hopes, was released in 2005. Despite being only fifteen minutes long, it was listed as one of the top local albums of the year by Minneapolis Star Tribune.
She completed and released a book of creative non-fiction titled Spiral Bound at the fourth annual Doomtree Blowout in 2008. In 2009, Dessa published Spiral Bound on Doomtree Press, a seventy-page collection of fiction and poetry.
Dessa's first solo album, A Badly Broken Code, was released on January 19, 2010. The singles from this album are "Dixon's Girl" and "The Chaconne." The album features production from Paper Tiger, MK Larada, Lazerbeak, Cecil Otter and Big Jess. MK Larada also designed the album art.
In 2011, Dessa released Castor, the Twin.
In 2013, Dessa released Parts of Speech. The singles from this album are "Warsaw" and "Call Off Your Ghost."
Dessa is a founding member of The Boy Sopranos, an almost all-female a cappella group, with frequent collaborators Jessy Greene, Aby Wolf and others. She also taught at the Institute of Production and Recording and the McNally Smith College of Music.
On March 2, 2012, Dessa presented "Mic Lines: Art, Ethics, and their Contested Connections" at Augsburg College in Minneapolis, Minnesota, as part of the three-day Nobel Peace Prize Forum .
Dessa was the host of Twin Cities Public Television's The Lowertown Line, a live music series, from 2012 to 2014.
- False Hopes (2005)
- Parts of Speech, Re-Edited (2014)
- False Hopes (2007)
- Doomtree (2008)
- Doomtree Blowout / False Hopes 13 (2008)
- FH:XV (False Hopes 15) (2009)
- Doomtree Standards Mixtape (2010)
- No Kings (2011)
- All Hands (2015)
- Sims – "No Homeowners" from Lights Out Paris (2005)
- Kanser – "No D in Erogenous" from Kanser (2005)
- Paper Tiger – "Speedmetal" from False Hopes (2007)
- Mel Gibson and the Pants – "Bit of a Buzz" from Sea vs. Shining Sea (2007)
- Heiruspecs – "Change Is Coming" from Heiruspecs (2008)
- P.O.S – "Low Light Low Life" from Never Better (2008)
- Paper Tiger – "Palace" "And the Camera" from Made Like Us (2010)
- Lazerbeak – "Bound" from Legend Recognize Legend (2010)
- Gayngs – "No Sweat" "Faded High" from Relayted (2010)
- p-teK – "This Bridge Is Burning for You" from Oh! What a Miracle! (2011)