The paper is an empirical contribution to the intention to remain at work until legal retirement age among different age subgroups of employees. Three groups of antecedents are analyzed: health condition, professional competence, and psychosocial work conditions, among two age groups of employees: 40- to 49-year-old employees and employees 50 years of age or older. The participants are employees from the service industry who are subject to annual control by occupational medicine (n = 280). They completed the VOW/QFT (Vragenlijst Over Werkbaarheid / Questionnaire sur les Facultés de Travail), a self-report questionnaire measuring several dimensions to understand the intention to remain at work. Hierarchical regression analyses tested the hypotheses. Results show there is clearly distinctive process between employees who were 40–49 years old and those over 50 in the explanation of intention to work until the lawful retirement age. Among the first group, perceived health and increase in abilities explained the intention to remain (psychosocial aspects were not an incremental explanation); among the second, it was the possibility of participation that motivated them to work. Implications concern the management of age and career: These are not the same factors that explain the intention to remain at different stages of the career. This research clarifies the respective roles of health, professional competence, and work conditions to understand the intention to remain by studying their incremental explanations and distinguishing two subgroups of age.