(1) Background: The start of vocational education is a challenge for many people whose careers are just beginning. The working conditions exact new physical and mental tolls that can have an impact on their state of health and health behavior. Well-developed health literacy helps to encourage greater self-responsibility with respect to health and safety in the workplace. This study aimed to contribute to the evolution of health-related interventions in vocational training and instruction. (2) Methodology: This cross-sectional study examined health literacy, health behavior, and states of health among trainees engaged in work-and-study vocational training in 11 professions at the start of their education courses in northern Germany. The data were collected using a paper and pencil format. (3) Results: The survey was approved by 47 vocational schools (response rate 14%), with 1797 trainees returning their questionnaires (response rate 36%). The average age of the overall cohort was 21, and 70% of the trainees were female. A total of 47% of the participants began their careers with sufficient health literacy; health literacy was problematic in 40% of cases, and inadequate in 13% of cases. Around 50% of trainees exhibited poor dietary regime and risky alcohol intake, while 58% reported having a medical condition that had been previously formally diagnosed. (4) Conclusion: There is a need to provide support for developing a healthier approach to work at the start of vocational training. © 2021 by the authors. Licensee MDPI, Basel, Switzerland.
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