According to John Dewey, self-government is the right and ability of everyone to participate actively in the regulation of their living conditions and social activities (Zask, 2010). It is part of a cooperative and reflective conception of democracy which simultaneously integrates all individuals into a self-governing community and an intelligent approach to solving political problems (Honneth and Farrell, 1998). Drawing from an overview of the writings of John Dewey and Jane Addams, this essay aims to detail and analyze the main challenges and obstacles to achieving self-government. Of primary focus are political contingencies, the concrete valuation and the constant re-actualization of this ideal according to an experimental and reflective approach, the exclusion of democracy from economic activities and the industrial world, the lack of lifelong learning opportunities, and the different forms of domination and paternalism in social relations.