The last nine months have been not short of challenging, overwhelming, heart-acheing individual and collective experiences which have and probably will continue to shape our ways of living for generations to come. This paper aims to provide a space in which to reflect and revisit our understanding of well-being and its implementation in light of these past few months and the continuous obstacles faced. It endeavours to offer some thoughts on how this unique time could be experienced to our advantage, and even in light of extreme pressure, stresses, and losses, how this opportunity for reflection can advise and guide our thinking and behaviours, values and beliefs, to new hopes and discovery that will hopefully provide some level of solace, inner strength and transformative growth. Through selected five pillars of well-being all discussed in turns, it aims to challenge and present alternative understanding and application of these pillars, that can hopefully continue to develop and grow as we are all exposed to new lived experiences. It concludes by inviting other colleagues and individuals in their own quest for making-sense and meaning-making of these challenging times.