Throughout the time of my teaching career, the tide has exposed changes in the nature of music, students and music education. This paper discusses teaching and learning in contemporary music at seven critical stages of 21st century music education: i) diverse types of undergraduate learners; ii) teaching traditional classical repertoire and skills to contemporary music students; iii) transitioning undergraduates through pre-service teaching into the workforce; iv) supervisory pedagogy for creative work higher degree research models; v) upskilling established teachers in musical practice and pedagogy; vi) professional development for adult community musicians; vii) disseminating learning back into music and teacher education. Constant elements in this landscape are musicianship, practice, creativity, employment, aesthetic expression and personal fulfilment. Shifting sands include characteristics of learners, pedagogy, delivery, technology, industry trends, and learning through consecutive career stages. The final scenario addresses challenges for musicians and teachers to maintain their creative practice through self-directed lifelong learning.