Family enterprises have been researched in traditional, stable market economies, to a lesser extent also in former socialist economies. A special focus has been on family enterprises’ sustainability and it has been discovered that one of the main pain spots is the change of generation related problems. Family enterprises can be sustainable only when they are prepared for a generation change. Family business culture and family traditions in Estonia have been broken. After Estonia regained independence in 1991, entrepreneurs started to restore previous farms and wished to continue family traditions of their ancestors; entrepreneurship started to develop and many people, especially in rural areas, started a family business. In 2012, these family entrepreneurs have a choice to make how to ensure that their family business will stay sustainable, how to pass family business over to their descendants so that the family business traditions won’t cease. This paper seeks to analyse factors that inhibit sustainability of family enterprises. The data sources are special scientific literature and the questionnaire surveys and interviews with family entrepreneurs conducted by the author over 2007−2011. It is possible to ensure that a family enterprise is sustainable only when the family entrepreneurs are prepared for the generation change. The present and future family entrepreneurs in Estonia can get information from this paper about the problems that may arise in connection with the generation change and knowledge to ensure sustainability of their family business.