The main objective of this study is to investigate a solution for the current lack of skilled workers in Europe and to optimize the utilization of expertise. For this qualitative study, 36 semi-structured interviews were conducted (with a purposive sample of financially independent (soon-to-be) retirees and employers). The thematic analysis revealed (1) on both the employer’s and recruiter’s side, there are many stereotypes and prejudices, as well as a lack of creativity about how to integrate these highly motivated specialists into the organization’s workforce; (2) as regards senior experts, there is a worry that their competences and commitment will be judged based on how they have been treated in recent years of employment. The results also indicate that searching for intellectual challenges and solving them with a team of co-workers is one of the main attractions for senior experts. We identified six main patterns for unretirement choices: learning and intellectual challenges, applying expertise, public perception of retirees, belonging and social connections, compensating for loss of status, and feeling appreciated. Appreciating, valuing, and channeling this drive to solve present-day problems independent of a person’s chronological age should be self-evident for organizations and societies.