The senior generation’s reluctance and indeed resistance to alter the status quo of the existing management and ownership structure of their family farm is undoubtedly strong within the farming community. This phenomenon has resulted in extraordinary socio-economic challenges for young people aspiring to embark on a career in farming. The reasons why older farmers fail to plan effectively and expeditiously for the future are expansive, and range from the potential loss of identity, status and power that may occur as a result of engaging in the process, to the intrinsic multi-level relationship farmers have with their farms. These so-called ‘soft issues’ i.e. the emotional and social dimensions involved, are the issues that distort and dominate the older generation’s decisions on the future trajectory of the farm. These really are the ‘hard issues’. This paper draws on three interrelated journal articles exploring the complex human dynamics influencing the decision-making processes surrounding farm succession and retirement to put forth a series of recommendations that sensitively deal with problematic issues surrounding generational renewal in agriculture, whilst also ensuring farmers’ emotional wellbeing in later life.