This project report is a self-reflection on the author's dual careers as a performing artist and as an arts administrator during the 12 year period between 1999 and 2011. Career experiences with 5 key arts organizations are discussed, with a chapter dedicated to each organization. The organizations included are The Western Stage, The City of San Diego Commission for Arts and Culture, The La Jolla Stage Company, Centro Cultural de la Raza and the City of Riverside Arts and Cultural Affairs Division. Within each chapter the author reflects on topics such as his greatest success and his greatest failure with each organization. Other topics examined are the author's experiences as a performing artist concurrent with each arts administration position and the lessons, concepts and ideas worth sharing that were garnered from each organization. It is the author's hope that this information may prove to be valuable to arts organizations and fellow artists who may find themselves on a similar path.