In ageing Czech society the age of retirement has become an important issue in debates on how to reform the pension system. In this article, which deals with the transition to retirement, the central question is asked what perspective the Czechs have on the timing of their retirement, and whether they are beginning to prepare themselves for the eventuality that they will have to retire much later than has been the case so far. Using results of various Czech representative surveys, the paradox of early retirement is found. It consists of contradictory links the Czechs know that their society has been ageing, that they have been living longer and that the number of pensioners has been increasing. They know also that after the retirement, their level of income (pension) will decrease substantially having a serious impact to their standard of living. Despite these facts the middle-aged and the elderly Czechs (45 years and older) not only oppose the increase in the statutory retirement age but they even prefer early retirement more frequently. Paradoxically, research conducted among the elderly has shown that many of those who are already retired today admit that they did not really want to retire. The article tries to find explanation of this paradox in the mentality of retirement created by the peculiar socialist labour market, and/or in the psychology of life course.