In this action research, the need for high schools to embrace a pedagogical shift to teaching 21st century computer and online literacy skills is investigated. This study explored areas of secondary and higher education, technology usage, and online pedagogies, 21st century skill frameworks, and brain function as they pertain to learning and decision-making, with the aim of comprehending the differing high school levels of preparedness for college in regards to 21st century skills. Through literature reviews, a research was designed to further explore the specific areas of a discovered gap in high school students' 21st century skills for college. Pre- and post-unit surveys, in combination with student assignment scores, were complied and examined to reveal a weakness in academic habits and computer literacy skills associated with 21st century learning. The study results support literature review findings of a breach between high school 21st century skill levels and collegiate level necessities. With these findings, it is suggested that instructors become choice architects, giving them the unique ability to nudge high school policy makers and students towards identifying the gaps between the analog and digital worlds of academia, generating more successful students as they transition to university online courses.