This study explores how German entrepreneurs manage work-life balance during persistent adversity, including economic downturns, resource losses caused by the Ukraine war, and the aftermath of the pandemic. Through 84 semi-structured interviews with 28 entrepreneurs over 12 months, we conducted sentiment and thematic analyses using border theory as a theoretical lens. The findings reveal distinct entrepreneurial responses to prolonged challenges and their impact on work-life balance strategies. Male entrepreneurs respond in a detached and objective manner to adversity, leading to segmentation strategies and strong work-life boundaries that protect their personal time with friends and family. Female entrepreneurs demonstrate emotional responses and integrate prolonged challenges into their entrepreneurial identity, creating permeable boundaries that affect their entrepreneurial decision-making and personal well-being. This research offers a fresh perspective on gender-specific responses to adversity and their impact on entrepreneurial work-life balance. This study extends the literature by demonstrating how gender-specific entrepreneurial responses shape boundary management strategies during persistent adversity, advancing beyond generic approaches to work-life balance.