Finnish governments have utilised a ‘stick and carrot’ approach to prolong work careers at the end by both increasing the official retirement age and offering financial incentives for people to work longer. This chapter explores Finnish male metalworkers’ and engineers’ thoughts regarding retirement and prolonging their careers in terms of how men’s motives change as they approach retirement age. Our interviews (conducted in 2010/2011 and 2017) indicated in both groups that the men had lost a great deal of their interest in work and most of them were ready to retire. Rather than focusing on their work ability, both metalworkers and engineers considered it important to secure sufficient health for life in retirement. Quite surprisingly, economic incentives did not seem to play a role in these men’s considerations of retirement in either of the groups, even despite the substantial income differences between them. Instead of additional money, the interviewees thought about their retirement plans in terms of health, mental wellbeing and work-related satisfaction. Our study suggests that future efforts to prolong work careers should therefore focus on improving working conditions and age-friendly work environments.