This contribution aimed at investigating how work-related reflection as cognitive efforts towards developing an understanding of work tasks, the surrounding work context, and one's professional competencies adds to the role of psychological empowerment and participative safety in predicting innovative behaviour and job crafting as two forms of proactivity. Quantitative data from 295 employees of micro, small, and medium-sized organizations in the information sector were collected with a cross-sectional questionnaire. For hypotheses testing, structural equation modelling was employed. The results of the study showed that work-related reflection and psychological empowerment were substantially related to innovative behaviour and job crafting while participative safety only played a minor role. These findings imply that jobs need to contain empowering and sufficiently complex work tasks that require reflection and provide occasions for reflective interactions to enable employees to create efficient routines and adapt to changes at work. Furthermore, experiences of empowerment need to be rooted in social interactions at work. Likewise, the value of reflection will only unfold if employees and supervisors regularly engage in reflection.