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This paper assesses the ways in which the characteristics of entrepreneurs from transition economies, and the extent to which they participate in making business decisions, affect their propensity to make rational/risky decisions in a work environment. A multicontextual analysis of entrepreneurial decision-making is provided, facilitating a better understanding and the further advancement of entrepreneurship in the transition countries of Montenegro and Serbia. Logistic regression and a Structural Equation Model (SEM) were used to assess data collected from a stratified random sample of 260 entrepreneurs. The results reveal that the demographic characteristics of entrepreneurs have a significant impact on their propensity to make rational/risky decisions. Elderly entrepreneurs with more years of service are more prone to make rational decisions in comparison to younger entrepreneurs, who lack business experience and thus rely on intuition, leading to risky decision-making. Additionally, the results show that the more involved entrepreneurs are in the decision-making process, the more risky decisions will be made; while more employee inclusion leads to business decisions based on rational thinking. The results also reveal that entrepreneurs in transition economies have formed attitudes towards the nature of entrepreneurial activity. Finally, these results reveal that entrepreneurs who consider levels of economic development, national culture, and intuition to be important when making business decisions are more prone to implement risky decisions. Considering the obtained results, this paper provides guidelines for the future research of this issue in transition countries and other developing economies. © 2022, The Author(s).