Family businesses, owing to their unique blend of family dynamics and business operations, often face distinctive hurdles that can significantly impact their sustainability and growth. This qualitative study delves into the multifaceted challenges that confront family business leaders, as seen through the eyes of family business owners, which is a missing aspect in the extant literature database. Through in-depth interviews and thematic analysis, this study aims to shed light on the key challenges family business leaders encounter. The findings of the study reveal that the family business leaders have challenges related to the succession planning, financial management, conflict resolution, communication breakdown, governance, HRM, and the evolving business environment in the day-to-day business operation. These findings further echoed the need for a personalized approach and support systems to face the challenges and to be successful in the long run. These results not only contribute to the existing literature related to the management of family business, but also provide a very practical use to the practitioners in increasing the strength of both the family and business while operating within the context with such complexity.