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Estonian and Latvian rural inhabitants enjoy many factors enhancing the quality of life, such as the peace and quiet of the countryside, fresh food and rural activities. However, these benefits are insufficient to overcome poor employment prospects in rural areas. Place-shaping practices have transformative powers that are instrumental in achieving sustainable change in communities. The process of reappreciating local landscapes creates memories of positive associations with symbolic meaning; it helps inhabitants to strengthen their sense of place identity and re-grounds their appreciation into a specific local context. Sustainable rural futures require conditions where inhabitants feel listened to and that are responsive to their needs. They also require inspirational leaders to facilitate change and create networks of opportunities, linking inhabitants to the outside world and resources. Leaders may play an important role of re-positioning local communities for the future, creating new experiences or new opportunities, which further feeds re-appreciation of place and enhances quality of life. In order to understand the main issues of the rural areas, two villages with active rural projects in Estonia and Latvia were selected to analyse the role that leaders play in the development of the area and the barriers to a more sustainable approach.