The demographic low, and thus the inevitable aging of the populations of economically developed countries, makes it necessary to extend the working life of citizens. Therefore, an increasing percentage of workers are representatives of the so-called “silver” generation, i.e., people over 50 years of age. The main objective of the study is to characterize the system of values, attitudes to work, and related expectations of professionally active women and men over 50 years of age and to determine whether, and if so, how the hierarchy of values, attitudes to work, and job satisfaction affect the further development of their professional careers. In order to achieve such a goal, a CAVI survey was conducted on a sample of n = 600 respondents. The statistical significance of the differences between the groups was tested with the Mann–Whitney U test. To verify the main hypothesis, ordinal logistic regression models were built. The results of the study were supplemented with elements of descriptive statistics. In the course of the research work, it was confirmed that there are significant differences between the studied men and women in the assessment of traits concerning their value hierarchy, attitudes towards work, and career prospects. Traits such as value hierarchy and attitudes toward work have a significant impact on the career development of both women and men of the “silver” generation, while job satisfaction shows a significant impact on career development only for women.