Over the past 25 years I have been intimately involved in the world of individual and organisational change within a host of different settings and with people from all walks of life; and during this time in my various roles as counsellor, educator, coach, and facilitator, I have been privileged to see the amazing capacity for positive human change. My natural curiosity and love of learning has led me on a lifelong quest to better understand what it is that enables people to change: from simple behavioural adaptations to major life transformations; from a shift in attitude to learning a whole new set of skills. The scholarly endeavours of a host of dedicated researchers that have built up a significant body of knowledge has been impressive; there is such a wealth of material that it would go far beyond the scope of this chapter to fully explore and do justice to the richness that is a defining feature of the scholarship of personal and organisational change. However, within this chapter, based on my years of experience, reflections, conversations, and explorations, my desire is to contribute to the field of Applied Positive Psychology (APP) by offering a series of observations and questions about our awareness and understanding of human change, and more specifically, how different modes of change might shape the way positive psychology is applied in practice.