The aim of this paper is to explore the social challenge of sustainable work systems and regenerative work. This is done by using complexity theory to grasp and understand the vision of sustainable work systems. A comprehensive literature review generated a theoretical framework for both sustainable work systems and understanding of complexity and in addition these two phenomena’s point of contact. Two case studies provide an empirical example and illustrate the potential in the conjunction of sustainability and complexity.A sustainable work system can be described as a simultaneous development and convergence between different levels and interests interrelated to the work organisation; from the individual perspective to the surrounding world of the organisation. A sustainable work system is characterised by having the capacity to regenerate and support the growth of the individual’s (employees) cognitive and emotional resources and at the same time maintain or increase competitiveness of the organisation. From the employee’s perspective this paper suggests that in order to reinforce and strengthen the individual, these same resources must be both recognised, adopted and have satisfactory support in the work organisation.This paper suggests that work organisations ought to create a work environment condition that supports self organisation, and acknowledge complexity and uncertainty as the normal state of reality.