Diana has worked since the age of fifteen. While a student at UCLA, many of her positions focused on education and human development. She worked for the City of Santa Monica's Parks and Recreation Department, leading the preschool program at Lincoln Avenue park, and directing the Teen Program at Jocelyn Park. Diana taught Spanish at the Bonner School, and also worked for the Perlman Learning Center, tutoring children with dyslexia, and honing her knowledge of phonics-based reading systems.

Upon graduation, Diana began teaching reading to kindergartners and first graders. During these latter four years, she was an evening student at Loyola Law School. She began her legal career as a labor lawyer where she focused on workplace equity and sexual harassment issues.