School-level educational interventions targeting learners from low socioeconomic backgrounds often have the long-term goal of enabling access to, and successful completion of tertiary studies. This study tracked the progress of alumni of an educational intervention two or three years post school, in order to investigate their pathways to their destinations of work and study. Forty percent of the alumni were successfully traced, and asked to fill in an online questionnaire. Of the 104 traced alumni, 80% reported good academic progress, despite false starts and changes in direction, which resulted in complex transitional pathways. The main factor disrupting a direct pathway through tertiary studies was a lack of finances. The alumni reported that many of the enabling factors for their tertiary success were legacy benefits of the school-level intervention. The benefits reported included a sound preparation for life and academic studies, and other benefits that the researchers categorised as developing resilience and grit.