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Entrepreneurship researchers’ interest in the cognitive dimension is growing (Baron, 1998, Cossette, 2010, Schmitt, 2015). Several authors (Filion, 2008, Grégoire, Corbett, & McMullen, 2011) have seen entrepreneurial cognition as one of the most promising areas of research on entrepreneurship over these past years. Clearly being oriented in this direction, this article aims to present the mechanisms behind the decision to take over a business by an external natural person/buyer following a professional break. To this end, the article uses an unprecedented analysis framework in takeover entrepreneurship (the theory of sensemaking). The “element” (Shapero, 1975) perceived as a determinant in the decision-making process of creating or taking over a business (Deschamps, 2000) is studied from the perspective of sensemaking. Drawing on an exploratory piece of research based on three case studies, we show that professional interruption constitutes an ecological change (Weick, 1979) generating equivocity in the future buyer, who will seek to rise by interacting with others. From these intersubjective exchanges comes a process of construction of meaning. We propose a modeling of this process, incorporating the factors of contextual influences highlighted by our research.