This article sets out to examine the effectiveness of five different post-16 study pathways and the impact that spending time away from education has on gaining employment associated with an undergraduate degree. It also explores advice and guidance for students looking at post-16 study options, higher education and employment. An initial online survey was used, followed by case studies to form a mixed-method approach. The findings suggest that a vocational pathway better prepares students for making decisions around employment and study in comparison to the more traditional A Level pathway. They also highlight that a period of one to four years after finishing post-16 study and starting undergraduate degree study is the most effective for students to gain employment associated with their undergraduate degree. Finally, it was found that most participants did not have positive experiences with advice and guidance regardless of their pathway.