Digitalization, robotization, artificial intelligence, and all kinds of new technologies that are known as Industry 4.0 or the fourth industrial revolution have great influence on the future of work because they will gather new jobs with new skills, and a majority of the senior workforce will probably have a lot of problems with those kinds of changes and challenges. The major objective of the paper is to recognize the dependence of the unemployment of the age category 55–64 upon selected explanatory variables. The explanatory variables were selected, and the expectations of their signs were presented in the research design. The secondary data of Eurostat and OECD 2015 has been used, covering the twenty-two member countries of the European Union (the countries that provided minimum wage were included only). The econometric analysis, specifically model specification and model quantification were the main methods used in the paper. The main outcomes and relevance of the model as well as its limitations have been compared with the findings of other authors in the discussion and implications for further research.