Transformation is a choice and an art. It is no linear process but a spiral going up and down within fixed boundaries, widening and opening up on the way to the top. The author of this chapter illustrates why the ‘deficient’ human species is dependent on specific skills and capacities to ascend that spiral staircase and that this requires a juggling act to keep five balls in the air simultaneously. He showcases that this path involves dealing with complex mental processes and that mastery can only be achieved through hard and disciplined work. This chapter is a call to take on this challenge and a warning that the ability to adapt, which has represented mankind’s ‘selection advantage’, is at stake in a world where our cultural achievements have enabled us to coevolve and create a culture beyond nature. At the same time, it reminds us that transformation is the very process by which we can best deal with uncertainties, contradictions and disruptions. As such, mastering the art of transformation is relevant for both sustainability transformation at the collective level and more well-being for individuals, determined by a mindset that is capable of staying open to what the future may hold and that favours a ‘both-and’ thinking over the ‘either-or’.