Entrepreneurs frequently encounter high levels of uncertainty, setbacks, and stress, resulting in negative effects on entrepreneurs’ well-being. Coping has been identified as a critical factor in becoming resilient to such adverse experiences. However, existing research often relies on aggregated coping frameworks, which oversimplify the complexity of entrepreneurial coping and offer limited insight into why entrepreneurs adopt particular strategies. This study explores entrepreneurial coping trajectories to better understand how entrepreneurs manage adversity and what drives their coping approaches. Based on semi-structured interviews with 30 experienced entrepreneurs and eight ecosystem stakeholders, we conduct a qualitative interpretative analysis of the dynamics of entrepreneurial coping. Our findings reveal that entrepreneurial identity influences coping behaviors and affects whether entrepreneurs employ adaptive or maladaptive strategies. This study contributes to research on entrepreneurial well-being by offering a nuanced understanding of entrepreneurial coping dynamics and informing interventions to foster adaptive coping of entrepreneurs.