Based on a sample of over 3000 primary and secondary school students located in regional and rural schools in Tasmania (Australia) this research had three aims: (1) to identify students' self-perceptions of schooling with a focus on high school completion (referred to as school retention); (2) to determine if gender, socio-economic factors, level of school absenteeism, and school setting (primary or secondary) influenced the students' responses; and (3) to identify which factors had the greatest influence on the students' aspirations to continue their schooling. A 42- item survey produced eight factors: (1) Teacher Support, (2) Aspirations, (3) School Organisation, (4) English Ability, (5) Maths Ability, (6) Friends, (7) Other Activities, and (8) Career Goals. Higher levels of absenteeism, lower socio-economic status, and transitioning to secondary school reduced scores on the factors. Girls had higher scores for three factors: (1) Teacher Support, (2) English Ability, and (3) Aspirations. Regression analysis identified Friends, English and Mathematics Ability, Other Activities, and Teacher Support as the 'best predictors' of students' aspiration to continue schooling. The implications of the significant findings for school practice are discussed with recommendations for interventions.