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This study is based on behavioral theories and has the purpose of determining the predictors and contingencies of strategic decision making within the strategic tripod framework and CEO age effect. Furthermore, we focus on the effect of the interaction of these aspects on strategic decisions. Multiple theories and concepts are applied in this paper, such as the institution-, industry-, and resource-based view, upper echelons theory, socio-emotional wealth, empathy, and so on. Specifically, we focus on why Chinese real estate firms decide to enter the aged housing market. By conducting an empirical study using panel data from 134 listed Chinese real estate companies, we make the following conclusions: Institutional pressure and competitor numbers positively affect, whereas slack harms, the likelihood of entry. Ceteris paribus, the resource effect is strongest when the institutional effect is the most significant. When facing institutional pressure, a firm with a CEO older than 50 is significantly more likely to enter the aged housing market than firms with a CEO that is younger.