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Through their transgenerational character, family SMEs raise questions about the place of anticipation in companies whose futures appear to be marked by their transmission to new generations. In this transgenerational entrepreneurial context, the objective of this research is to discuss the place of anticipation in the managerial practices of managers of family SMEs and to explore the different types of behavior of these managers vis-à-vis the future. After first discussing the future orientation of transgenerational entrepreneurship, we present the results of five case studies coupled with a survey of forty-three companies in the pastry sector in Alexandria. Both the case studies and the survey reveal different orientations regarding the future. We propose a typology to facilitate discussion of these orientations. The results show the essentially operational nature of business leaders' anticipation, underlining the contrasting character of transgenerational entrepreneurship. Research reveals that managers of these companies diverge significantly in terms of their relationship to the future, although there is a dominant group of “futuristic” thinkers who outnumber the “presentists” two to one. Taking different forms, the relationship to the future is thus very present in these companies, and not only from a transgenerational angle.