There are widely expressed concerns about competitive stress in the upper secondary schools of Australia, and there is good reason for asking whether the pressure placed on upper secondary students is necessary. Is the pressure on upper secondary students in Australia productive, and are the assessment systems at upper secondary school attaining an appropriate level of productive pressure rather than unproductive stress? On the other hand there is the opposite concern about international competitiveness of Australian students. There is also a concern about the levels of basic skills currently attained by the graduates of secondary schools in Australia. And on the other hand there is concern that the focus of attention in upper secondary school is still too academic, and that insufficient attention is given to the personal skills and attitudes (such as teamwork, adaptability and innovation) that young people will need to cope with the challenges of the future. Upper secondary school seems to be focussed on gaining high tertiary entrance scores rather than developing either basic enabling or higher-order thinking skills. There are evident contradictions in these concerns about more and less competition, the need for more attention to basic skills and more attention to higher-order thinking and personal and social skills. As we move towards 2020 there is reason for asking whether the contradictions to be seen in these concerns about upper secondary schooling in Australia can be lessened, and even, perhaps, resolved. If we look back, how did we get to the current position in upper secondary school in Australia? And as we look forward, how might we better arrange assessment and certification at upper secondary school and the transition from school to work or further education in the future?