A recently published study introduced a new instrument (HLS-EU) for the measurement of health literacy (HL) and comparative data at population level for this measure across eight European Union (EU) countries, and revealed significant differences in HL at population level. The HLS-EU instrument consists of items that aim to assess respondents' estimation of difficulties regarding different health-related tasks, and it is therefore a measure of subjective HL. With help of a two-step approach, the present study, which was conducted in Austria, aimed to investigate individual experiences and factors that are associated with high or low values of subjective HL as measured by the HLS-EU scale. In a first step, qualitative data from 20 cognitive interviews for the short version of the HLS-EU scale were analyzed. In a second step, the preliminary results of the qualitative analysis were validated with the help of a standardized survey (n = 800). Results show that subjective HL may be grounded either in high empowerment, including high personal and social skills and resources, or in a lack of health-related experience and reduced critical contemplation but high trust in the health system, which is paired with paternalistic preferences. As a conclusion, it is recommended that research should acknowledge the heterogeneous and multidimensional nature of subjective HL.