Elena Antonacopoulou and Regina Bento offer a chapter called “Choosing Our Cross with Wisdom: A Folktale for Living and Leading”. This chapter is inspired by the folktale about a man who constantly complained about the weight of his “cross,” but then, in a dream, was given the opportunity of choosing his own cross. In this folktale, we come to appreciate suffering as an inescapable part of life. Yet, the wisdom of our choices influences our ability to deal with suffering and allows it to become a source of personal growth. Such choices can influence not only the cause of our suffering (for example, when the suffering relates to something that is conceivably under our control); but, more importantly, those choices can influence the effect that suffering has on us, even when we cannot do anything about the suffering itself. But how can we “pick” (choose) our cross with wisdom, so that we can also “pick up” and carry it through life, in a sustainable way, that opens us to joy, and helps us greet both happiness and suffering with equanimity? Here we draw from various religious, spiritual and philosophical traditions to examine the wisdom of picking up a cross in a way that involves assessing both the burden (the weight to be borne) and the bearer (our capacity to bear that weight) in a lifelong search for meaning. We then explore the challenges and opportunities this entails for leaders as those, who can influence the burdens of others, and their capacity to bear burdens. And then this chapter concludes by reflecting about the role of leadership education and development in helping prepare future leaders to pick up individual and collective crosses with wisdom.