There are Stories that we are told, stories that we tell, and Stories that are told through us. This text sets out to ask whether self-regulation is a tool to support the progressivist educator or something that undermines the goals of progressivism. But we cannot avoid the footnotes or philosophy in educational research. What is ‘progressivism?’ How does its theory connect or disconnect from its practice? Can it function or live up to its name if those who call themselves ‘progressive’ teachers or parents are distracted by The Question of ‘How do I get them to do what I want them to do?’ And, what about the follow-up fear of control or chaos or the belief that ‘Those kids can’t handle their freedom?’ Employing an ‘out-of-the-box’ narrative academic writing approach, weaving stories from personal parenting and teaching moments with case studies, the questions surrounding self-regulation reveal some surprising answers. Can the narrative surrounding Classroom Management co-exist with progressivist educational goals or the tool of self-regulation? Can democracy be promoted, taught, or lived without praxis? / Graduate