Recent scholarship on the African middle classes focuses on a middle-aged cohort and generally assumes that social status remains stable over the life course. This contribution argues that a struggle to retain one’s social class across the life course is part of middle-class life in Kenya. I focus on those who currently lead a decent life in the city and prepare for their life after retirement. My ethnographic data suggest that the middle classes cannot afford life in the city once there is no regular income. I argue that entitlements and resources need to be saved and invested during an economically productive phase to lead a decent life after retirement outside the cities.