Retirement is a major life transition which is associated in public discourses with reduced economic productivity and a raft of personal vulnerabilities. Consequently, governmental, health and employment sectors have promoted ‘active’ planning of affordable and ‘healthy’ retirements. This study presents a qualitative exploration of retirement transition and preparation experiences among 52 men and women from rural and urban areas of North East England, United Kingdom. The sample was diverse in terms of social class, income level, health status and type of work exit. Health, finance, social relationships and third-age opportunities were required resources for a good transition into retirement, and a degree of planning was required to mobilise these resources. However, the degree of choice and control around the transition to retirement was highly variable and socially structured. The notion of planning was embedded as a normative practice, particularly in relation to finances, but the practice of planning was highly contingent primarily due to personal circumstances (ill-health, bereavement, relationships) and work exit (redundancy, work stress, changes to shift patterns or hours). The findings offer insights into the reasons why many people do not plan and indicate that many of the assumptions associated with retirement planning warrant further consideration both theoretically and practically.