This research looks at the barriers to sustainable development Squamish, BC., a costal town that is in transition from a resource to non-resource based economy. Smart growth guiding principles have been used to shape the transitional processes; most plans however have yet to be implemented. Action research was used to guide this thesis, and data generated from District staff and community participants suggests that limited or inefficient communication/education has not motivated community engagement in sustainable development plans. The research explores District lead sustainable development initiatives and identifies barriers to their implementation. The research also identifies community values and explores how these values align with initiatives. Suggestions that support the principals of the Self Determination Theory (Ryan & Deci, 2000a) are put forth to internally motivate community collaborations, and engagement to encourage implementation of community-based sustainable development plans.