This document discusses leadership challenges in a volatile, uncertain, complex and ambiguous (VUCA) world. It argues that leaders need opportunities to quiet their minds and gain new perspectives in order to develop insights. The document proposes that a leadership experience aboard a sailing yacht could provide such an opportunity. Leaders would learn about leadership through experts, practice sailing, and captaining the yacht while leading an inexperienced crew. This simulated experience in a new context is intended to challenge leadership thinking, build self-awareness, and generate insights that could help leaders navigate today's VUCA world.