The common destinations by students after graduation are further education in universities, employment in local and far away businesses, and starting their own businesses as entrepreneurs. The requirements and expectations of these destinations differ widely across the different fields of study, the complexity of skills required to succeed in jobs within the different industries, and the resources available to support small businesses in a community. Regional variations in natural resources also pose structural differences in the types of knowledge and skills required to succeed in further education, local businesses, and entrepreneurship designed to offer services to local businesses and individuals. We have employed an approach that helps us capture granular level data and combine that data with those captured from identified destinations requirements, and expectations to ensure learning is personalized.