With the labor market and work environments becoming increasingly dynamic, the question of how young people can find their way to a sustainable professional future becomes ever more complex. This paper looks from different perspectives at apprenticeships, at their advantages and limitations. The first step is a description of the prerequisites that are necessary for a sustainable career choice. In this respect, the role of career guidance is particularly relevant, as guidance needs to take into account both individual characteristics as well as labor market aspects in order to support a sustainable career choice. Based on a comprehensive critical literature review of current interdisciplinary and international papers, as well as of basic career choice theory literature, the theoretical framework is set out and linked to empirical results. The conclusion emphasizes the high importance of apprenticeships for the holistic personality development of young people and a positive as well as a sustainable effect on their lifelong employment careers. It should be stressed that this success depends, to a large extent, on the structure of the vocational education and training system, on labor market developments, and on individual advanced qualifications in the course of working life.