What are the key challenges in becoming a professional singer of classical music? This chapter is written from the perspective of a professional singer who has been taught using the traditional highly personalised ‘humanistic’ approach to music education, which starts in childhood with choirs, and then focuses on advanced voice technique, development of musical memory, as well as the acquisition and application of linguistic and historical concepts in approaching a score. It raises the question is in how far on-line learning courses can be helpful to augment this kind of training and in how far ideas from a humanistic approach can be transported into the domain of on-line music learning.