Background: Family businesses contribute significantly to global economies but face unique challenges, notably in succession planning and generational transitions. These challenges are amplified due to the interplay of personal relationships, emotions, and family dynamics. Existing research offers quantitative insights into this field; however, the nuances of human experiences and perceptions in different cultural contexts remain underexplored. This study seeks to bridge this gap through qualitative exploration of family businesses' experiences and perceptions in Sweden and Canada, focusing on succession planning and generational transitions. The research aims to provide a more nuanced understanding, thus contributing to more effective, culturally sensitive, and practitioner-oriented strategies for managing intergenerational transfers. Purpose: This study delves into the complex process of succession in family businesses in Sweden and Canada. By emphasizing practitioners' lived experiences, it aims to identify prevalent patterns, contribute to the current literature, and potentially inform enhanced succession practices. Method: Applying an abductive research approach, the research combined hermeneutic and phenomenological methods, employing semi-structured interviews with nine family businesses six in Sweden and three in Canada as the primary data collection method. This approach allowed for a rich understanding of the phenomena. Conclusion: The research underscores the complexities of succession planning in family businesses, emphasizing the importance of open communication, trust, personal ties, and effective succession planning. Our findings diverge from a one-size-fits-all approach, revealing a multifaceted reality that requires a more adaptable, context-specific approach to succession planning. This research contributes to a deeper understanding of succession processes in family businesses, presenting valuable insights for future research, policy decisions, and practical business strategies.