The term strategy appears to be amongst the 1,000 most commonly used words in the English language, particularly in a business context; yet it can have a multitude of alternative meanings. The concept of strategy in a military or political context has remained prominent throughout history, and has been discussed by such major writers as Shakespeare, Montesquieu, Kant, Mill, Hegel, Calusewitz, Liddell Hart and Tolstoy. Strategy requires learning, development and adaptation. In contrast, relatively stable situations, with low levels of complexity and uncertainty, may benefit from a top-down approach. However, as the environment becomes messier, more turbulent and uncertain, the process of defining a strategy becomes more experimental and driven from the bottom up as new insights and learning emerge from interactions and discovery. The idea of a strategy journey provides a platform for action and offers an opening for beginning to address organisational learning in the context of strategic management and improvement.