Today's social and political context is filled with environmental elements that both support and work against deep, participatory democracy. I argue that certain democratic habits should be nurtured through a supportive formative culture, especially in schools, in order to best achieve good democratic life in the present context. My aim here is to fill some of the gaps within the picture of democracy that Dewey paints, to employ Dewey's unique understanding of habit formation and change as key elements of political agency, and to suggest some fruitful avenues for citizenship education in today's social and political context.