As geographic information systems (GIS) and science have evolved from programming and development to include application and modelling, design and institutional implementation, and the theory of geographic information, the need for specialized, career-specific instruction has consequently increased and diversified. The traditional college or university approach of formal GIS instruction is proving outmoded and insufficient to satisfy the needs of a widening set of learners in need of specific, sometimes current awareness and sometimes remedial learning. The audience can be learners in high school, community college, undergraduate or graduate school, pre-service or in-service professionals, or even those new to the profession. Recent advances in both technology and applications of GIS indicates the need for three major interacting ingredients to provide such a multi-path entry into GIS: online learning and personal learning environments (PLE) combined with conditions of heutagogy. This chapter describes how this approach might be achieved with existing technology and approaches.