This study attempts to analyze retiree’s retirement experiences including retirement planning, problems encountered, and adjusting strategies so as to clarify the relationships between them, and to explore the ways that could assist retiree’s adjustment to retirement. Both in-depth interview and focus group methods were used to collect the retirement experiences of 24 retirees. There are four major findings. First, three types of retirement planning can be categorized including ‘to live without planning’, ‘to build castles in the air’, and ‘planning and preparing’. Second, the two types, ‘to live without planning’ and ‘to build castles in the air’, are more likely to face the problems including ‘having too much time’, ‘interacting with family members’, ‘maintaining social relationship and interaction’, and ‘bridge-employment barrier’. Third, although retirement should not be considered as the same as the aged in life cycle, the adjusting problems caused by ageing still exist during the retirement period. Fourth, differences on retirement planning and adjusting exist between genders. It is not recommended to standardize and simplify the retirement planning. It is suggested to go on investigating various groups of retirees, and to provide multiple ways and lifelong assistances to their retirement planning.