In 2020, the EtonHouse International Education Group (EtonHouse) celebrated its 25th anniversary. Under the leadership of Ng Gim Choo, founder and managing director, EtonHouse has become a renowned education provider noted for its well-designed inquiry-based curriculum. Since its initial expansion in Singapore, the institution has spread across the world. Throughout its history, EtonHouse has faced many crises. However, employing paradoxical leadership, Ng has managed to accommodate conflicting demands and guide EtonHouse away from adversity. In early 2020, the coronavirus pandemic (COVID-19) posed an unprecedented challenge to EtonHouse. In addition to developing business strategies in response to COVID-19, Ng has been considering whether the time is ripe for handing over the reins to Ng Yi Xian, her son and EtonHouse successor. This multifaceted case study focuses on paradoxical leadership, women entrepreneurship, crisis management, and family business succession. It presents the entrepreneurial journey of a female protagonist, Ng, who established EtonHouse out of a passion for education and illustrates how she successfully addressed paradoxical challenges and navigated the company through crises. The dilemmas addressed in this case study concern whether Ng should delegate authority to her son to manage the COVID-19 crisis, and which EtonHouse should take to cope with COVID-19.