The purpose of the study was to examine the experiences of current high school students and teachers in Ontario regarding their experiences with personal financial curriculum and teaching at the secondary level, and to identify the ways in which this important educational experience may have helped prepare students to become financially literate. We considered this overarching issue using a transdisciplinary lens from the perspective of the three stakeholder groups. Using a case study research design, the first of its kind in Ontario or Canada on this topic, We utilized interviews and artifacts to uncover student and teacher experiential data across three high schools in southeastern Ontario. The major findings were that current students and teachers perceived curriculum and teaching experiences as seriously lacking in effectively preparing them to be financially literate, and that a fundamental reorientation around transdisciplinary, student-led learning was key to transforming such learning into a more meaningful and valuable educational experience. With mandatory, properly supported, student-oriented (transdisciplinary) instruction, the potential exists for more effective and valuable learning, resulting in better equipped high school students who were properly prepared to successfully navigate financial issues and the path ahead.