Across the globe many nations have found engaging young people in the post compulsory years of school to ensure their transition into economic citizens is challenging. Governments are focusing on developing initiatives and programs to connect young people in education and training as preparation for the workplace. In Australia the use of Applied Learning as pedagogy is emerging as a valuable tool in the delivery of curriculum to engage young people in education. Educators who use Applied Learning pedagogy develop curriculum that is relevant to student interests and needs, connected into communities and results in young people acquiring workplace skills. One such program in Australia is the 'Victorian Certificate of Applied Learning (VCAL), offered in years 11 and 12 of school and firmly grounded in Applied Learning pedagogy. The challenge for many educators is, and has been, that there are marked differences between VCAL pedagogy and curriculum and the pedagogy and curriculum they may have previously used in senior school programs. This paper draws on research that explores the professional learning experiences of Applied Learning educators, in the context of the VCAL. I argue that general professional teaching experience alone is not necessarily adequate preparation for teaching in the VCAL program.