Science, Technology, Engineering and Mathematics (STEM), including Computer Science (CS) are fields that are in great demand globally. This study's purpose was to explore the nature of the educational pathways, critical factors and commonalities/differences leading to CS undergraduate enrollment through the male and female perspectives focusing on personal/home, academic/attitude and psychological factors underlying the Social Cognitive Career Theory factors. Purposive sampling method was used for this multi-case study, comprised of CS undergraduate upperclassman. Participants shared their perspectives on their CS educational pathway via three interviews and journals. Thematic analysis of narrative for both individual and cumulative group analysis, plus researcher journal and drawings, enabled an interpretivist lens on the participant's voices. Five themes were identified in connection the participants educational pathways to and within CS: family role model, sense of belonging, growth mindset, good teachers, and you have to want it. Students' early exposure is essential and most influential within family connections. Students need a sense of belonging; and need to have educational experiences and strong foundations in STEM core disciplines in order to be successful and progress through more technically oriented educational pathways. My findings align with much of the relevant literature: early exposure and a sense of belonging is essential; students need strong core STEM experiences to pursue successfully STEM educational pathways. Recommendations for policy, practice and research are highlighted in the manuscript. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]