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New and emerging technologies pose a serious challenge for the future of employment. As machines learn to accomplish increasingly complex production tasks, the concern arises that automation will wipe out a great number of jobs. This paper investigates the relationship between the risk posed by the automation of jobs and individual-level occupational mobility using a representative German household survey. It provides an overview of current trends and developments on the labor markets due to the automation of jobs. It also describes the most recent dynamics of self-employment and relates it to the risk of the automation of jobs. The results suggest that the expected occupational changes such as losing a job, demotion at one’s current place of employment, or starting a job in a new field are likely to be driven by the high occupation-specific risk of automation. However, the switch to self-employment, both with and without employees, is more likely to occur from paid employment in occupations with a low risk of automation. Hence, the rising level of entrepreneurial activities is less likely due to jobs becoming obsolete over the course of automation, but rather due to the high number of opportunities offered by the digital age. The issues addressed within the paper provide room for further investigation. Particularly, an important question concerns which additional skills workers in jobs with a high risk of automation should acquire in order to make themselves less susceptible to the negative consequences of such a change. More research is needed in order to develop educational strategies to make workers less susceptible to job loss due to automation.