Starting with reflections on the pathologies and potentialities of work for impairment, respectively development of health and well-being, this chapter draws on the concept of Real Utopias to outline a positive vision of democratic, healthy, and ecologically sustainable organizations. The first section introduces the concept of Real Utopias with regard to democratic organizations, characterized by structurally anchored employee participation, collective ownership, and individually perceived participation in decision-making. Associated is the vision of a prefigurative transformation toward a more democratic and just society. The second section scrutinized concepts of healthy workplaces and the theoretical mechanisms and empirical evidence for the role that democratic organizations can play in realizing this vision. The third section reviews the literature on the Real Utopias of ecologically sustainable organizations, including concepts of degrowth, green entrepreneurship, and the Economy for the Common Good. All sections problematize the dialectic antagonism between democratic, healthy, and ecologically sustainable organizing and the profit-maximization, growth, and cost-externalization imperatives of neoliberal capitalism. The last section attempts to integrate the hopeful visions of the three lines of research while calling attention to the status quo of a socially corrosive and ecologically destructive mode of economic organizing. It also cautions about the risks that autonomous, motivating, and meaningful work can imply for employees’ overcommitment and self-exploitation. Deeper ideological foundations that elevate work to the center of human existence and sociality are problematized, and implications for the dialectic process of realizing Real Utopias are discussed.