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Diana Calderon's work experience begins in 2004 as an Assistant Language Arts and Art Teacher at Diegueno Country School. During this role, they educated students in language arts, provided tutoring for reading skills, and facilitated arts learning for students in 1st-6th grade. In 2010, they started their own business called Be Clutter Free, offering professional organizing services. Diana helped clients clean up and organize various areas of their homes and provided them with skills to maintain the organization. In 2011, Diana held the position of Vice President/Director of Operations at Ladies Stardust, where they managed and directed special events to raise money for various causes. Diana planned and negotiated terms with companies and individuals involved in the events. Additionally, they worked as a Sales Associate and Marketing Assistant at VAVi Sport & Social Club, where they assisted in making sales for adult recreational sports leagues and executed marketing plans.

Diana Calderon's education history includes attending Point Loma Nazarene University, where they studied Business Administration (Management). However, the specific years of their enrollment and whether they obtained a degree are not provided. Additionally, they also attended Mesa College, although no details regarding their degree or field of study at this institution are mentioned.