The Finnish pension reform of 2005 introduced the concept of a flexible retirement age. Drawing upon a longitudinal study of older Finnish employees, this article examines the extent to which individual propensity to delay retirement is influenced by choice or by chance, and examines the effects of the interplay between chances and choices in affecting longevity of employment. The results suggest that the flexibility in the organisation of the end of the working life is biased towards the better off. They also show that the interplay of choice and chance in the retirement process is firmly tied to the existing age-arrangements and economic trends. The conclusions examine the implication of these findings for divergent routes towards late retirement.