This chapter explores the challenges employees face pre- and post-retirement, after contributing a significant part of their lives to organisations. The chapter attempts to identify retirement policies and practices in two different scenarios. First, for the employees of organisations in which employees continue their careers. Second, for employees switching from one job to another. This will effectively help in exploring the state of retirement in public and private sector organisations in the Indian context. Careers in public sector organisations in India have long been associated with security in terms of pension after retirement as a significant social security initiative. The chapter addresses the characteristics of the Old Pension Scheme (OPS) and New Pension Scheme (OPS) in this context. Further, employees emancipate financial and psychological changes regarding post-retirement life at the closing years of their careers, and this chapter highlights the steps that they can take to mitigate these changes. The chapter also focuses on factors that lead to the requirement of a stable retired life. Retired employees possess skillset and experience from their jobs, and the chapter looks to explore how it can be utilised once they retire. Resilience and self-efficacy, as two important critical behavioural traits are examined for retired employees. This would not only open up opportunities for retired employees to contribute in a second career post-retirement, but also stay relevant in their local communities, as well as look at organisation policies that embrace employees from different generations to address their challenges. Finally, the chapter concludes by identifying critical areas of focus for pre- and post-retirement employees to lead a stable retired life and the responsibilities of organisations and government towards enhancing social security measures for improving the standard of life post-retirement.