This article draws on our backgrounds as adult educators in Ireland and our experience at Highlander in 2014. We review our development as critical educators, exposed to deep inequalities in Irish society. We explore role of popular education in fostering social change, beginning with the commitment to equality and freedom, whereby, we produce emancipatory knowledge with students and participants. This learning process is more explicitly political and collective than individual psychological concepts of learning. The Highlander experience provided the opportunity to interrogate related assumptions that underpin the concept of leadership, pointing toward a more collective and political framework. The article uses feminist critical theories as lenses for this interrogation, holding that equality and freedom are mutually constitutive principles of critical practice. Popular educators foster critical thinking and reflection. The Other’s Tools, drawing on the precept that traditional thinking reinforces the status quo. These critical thinking tools are vital to question the assumptions that power and control in society as individualized or de-politicized. We take this learning into our practice in Ireland.