A key requirement for being an integrated member of our achievement-oriented society is the successful transition from school to work. This article aims to present a multi-dimensional point of view on de-standardized vocational orientation processes. Vocational orientation therefore is understood as an active, constructive process of young adults, which are socially and institutionally bounded. Data is based on a mixed-method design with 406 young adults who completed a standardized questionnaire and 12 qualitative interviews. With this design, we aim at answering the following questions: (1) which patterns of risk can be identified and (2) how representatives of different risk patterns describe their individual vocational orientation process. Three groups of risk patterns were conducted by latent class analysis, which differ not just in terms of individual factors but also regarding social resources of family, school and workplace. If we take a closer look at the individual perception of vocational orientation by representatives of these groups, vocational orientation has been perceived differently depending on one’s agency.