This article explores our experiences as faculty implementing a five year sustainability strategic plan within the Outdoor and Environmental Education (OEE) curriculum centre during a time of organisational restructuring. This paper builds on the work of Jansen and Boardman (2011) who describe the process of developing the strategic plan and some initiatives arising from it. Now at the end of the five year timeframe and with the benefit of hindsight, we describe some of the problematic aspects of our sustainability initiative. The role of a strategic plan appears crucial in providing a general bearing, however remaining ‘true’ to a small centre and its vision also limited possibilities for interdisciplinary sustainability. We discuss how disruptive organisational changes provided unexpected opportunities for our sustainability initiative. The ongoing journey through ‘cutty-grass thickets’ and ‘clearings’ for sustainability is described with a view to providing inspired self generalisation for others on a similar journey.