Drawing upon the concept of personorganization fit, the present work shows ways how to account for changes in todays working environments by adapting established models of work analysis and work design, as summed up by the keywords “MayWantCan”. “May” applies to establishing working conditions that allow for learning and personality development by designing tangible work tasks (proximal aspect) as well as normative structures (distal aspect). “Want” refers to motivational contents and processes, aiming at psychological need satisfaction. “Can” indicates processes of competence acquisition, preservation, and extension. Corresponding to the keywords, three empirical studies were conducted, aiming at the expansion of established models of work design. Study 1 addressed the perspective of “May” by testing empirically an integrated work design model consisting of beneficial learning demands, supportive job resources, and detrimental job stressors. An additional contribution demonstrated the paradigmatic application of the model to office work. Study 2 approached the integration of the perspective of “Want” in a work design model by selecting work characteristics according to their contribution to or their interference with psychological need satisfaction. Study 3 expanded upon an aspect of “Can” by combining self-leadership as a personal resource with work characteristics in order to assess unique and joint effects on motivation and health impairment. In order to implement and integrate the three perspectives of “May, Want, Can” into a continuous process of work designwhile taking into account prospective, differential, and dynamic strategieswork enrichment of workplace health and safety staff is proposed. Being pivotal enablers and promoters of work that supports health and performance, safety specialists, occupational physicians, and work psychologists need to work under favorable conditions themselves in order to accomplish their task effectively. Therefore, study 4 analyzed the status quo of the three professions labor situation in Austria. The integration of the four studies is outlined and discussed. Finally, a conceptual framework is introduced that captures changes in the working world from the perspectives of organizations and individuals and identifies the task as both the interface and the crucial design element of personorganization fit.