To aid with a serious shortage of empirical studies on generational human resource management (HRM) preferences, Chapter One aims to add to the discussion in two ways. Firstly, by providing an extensive theoretical systematisation of HRM practices which are likely to be the most effective for achieving high performance from the two prevailing generations in the contemporary workforce (Xers and Yers), and secondly by exposing empirical evidence from a comprehensive study on the topic. Chapter Two explores the engagement levels of Generation X and Y HR practitioners in South Africa. However, reference was also be made to the Baby Boomers in order to indicate the cross-impact among the three cohorts. Shifting to a focus on health between generations, Chapter Three covers the use of online health resources and levels of eHealth literacy among random samples of 996 Baby Boomers from the US, UK, and New Zealand (NZ). In conclusion, Chapter Four argues that in order to have sound mental health, a baby boomer will need to develop ways of challenging the brain and protecting short term and long term memory by regular brain activity and social interactions. Every individual is different but the general guiding principles can be personalised for each individual and practiced as a routine in daily life.