Transition has an impact upon the emotional and social development of the individual as well as academically. This paper argues that transition is not a one-off event but is an ongoing process that is repeated over time. In entering further education (FE) the impact of transition in the move from formal schooling to post-compulsory education is no less daunting. Emerging independence and exploration of self-identity are fundamental in adulthood; however, individuals often need guidance and support during this process. Using an interpretive methodology, the voices of key stakeholders in the transition to FE were sought and recorded to explore and inform good practice. Data was collected using online and paper questionnaires, interviews and focus groups. Findings concluded the value of active and supportive relationships between learners and practitioners and between learners and their peers during the transition process. Nurturing effective practitioner-learner relationships, with opportunities to visit the setting promoted increased engagement by learners and facilitated learner identification with the learning environment, thus ensuring smooth transition.