Jeff Dieken was raised in Cedar Falls, Iowa and attended the Cedar Falls Community School District and Malcolm Price Laboratory School (NUHS). After graduating high school, in 1989, he joined the US Air Force and was stationed in Rapid City, South Dakota where he worked as a medic in Obstetrics/Labor and Delivery. In 1993, he left the active duty Air Force continuing in the Air National Guard until 1995. In August of that year he enrolled at Hawkeye Community College and transferred to the University of Northern Iowa in 1996. He graduated in 2001 with a BA in Secondary English Teaching. His teaching career began in the Waterloo Community School District where he taught for 5 years teaching Freshman and Sophomore English, Theater Arts, World Literature, and AP Literature. In 2006 he left the WCSD to pursue an administrative position in the Hudson Community School District and to start a Principalship Cohort at the University of Northern Iowa. In 2007 he moved from Hudson Middle School dean of students to Hudson High School principal. He completed his MAE in Educational Leadership in 2008.