Rapid technological advancements, globalisation, environmental crises, and ongoing conflicts have contributed to an increasingly quickly changing social, cultural, and work environment for current and future generations. In this paper, we argue that the traditional schooling system and approaches to curriculum and pedagogy that are based on nineteenth century industrial age models might reach their limit to prepare students sufficiently for the expectations and challenges of life and work in future. While so-called 21st-century education has seen a nominal change in classroom layouts and increased use of teaching technology, we would argue that not much has changed in terms of the underlying structures of schools and the mostly pre-described curriculum schools and teachers must operate under. While current education systems struggle with many challenges from teacher burnouts to increasing student dis-engagement (e.g. rising truancy in New Zealand), we posit that new challenges lie ahead that will further disrupt, if not implode, current approaches to schooling and curriculum. Drawing on theories such as Biesta's "World-Centred Education" and Pinar's notion of "Currere" to reconceptualise curriculum, we would argue that schooling needs to move away from the traditional 'static map' of curriculum content to a more dynamic approach to schooling that allows teachers and schools to chart new territory, together with their students, for a rapidly changing future. As guiding compass of sorts for dynamically exploring an uncertain future "with" students, we propose Teschers educational approach to Schmid's "Art of Living" as a starting point.