The decision to exit or take over an entrepreneurial venture represents a crucial turning point in entrepreneurial life-cycle. Exiting an entrepreneurial venture can create opportunities for others who wish to become entrepreneurs through the acquisition or inheritance of existing companies. This important decision has profound consequences that extend to various stakeholders, including owners, employees, suppliers, and other business participants. The situation in Croatia further emphasizes the importance of the business transfer issue, especially due to an aging population. According to the UN, Croatia ranks among the top ten countries with the highest percentage of people aged 60 and over in the total population. This fact underscores the relevance of the challenges associated with business transfer, given the large number of companies established in the 1990s that will soon need to plan for the transfer. It is estimated that as many as 16,590 businesses, whose owners are approaching retirement, need to initiate the business transfer planning process. These businesses employ approximately 179,000 workers. In light of these demographic challenges and the need to preserve business continuity, it is of paramount importance to recognize the significance of thorough planning and implementation of the succession process to ensure the sustainability of the company and the preservation of jobs. At the same time, the psychological aspects that entrepreneurial founders face when making the decision to withdraw from business must not be overlooked. The main objective of this paper is to highlight the issue of ageism and explore the psychological pressures and challenges faced by small and medium-sized business owners during this process. It is important to understand how these factors can influence decision-making and how to cope with them to achieve a successful business transfer. The psychological consequences of business liquidation are significantly more challenging than transferring it to family members. Transfer to family enables the entrepreneur to maintain an active role and a sense of control, while liquidation results in a sudden cessation of business activities without a replacement role, which can lead to identity loss and stress. It is crucial to carefully consider the decision between these two scenarios, as explored through interviews with two entrepreneurs, to avoid unnecessary psychological difficulties.