One teacher's experiences teaching English as a Second Language (ESL) to adults in community-based programs are drawn upon to illustrate how ESL syllabus design can better reflect the conditions that attract students to community agencies, and how the agencies can better serve students uninterested in or disadvantaged by formal educational institutions. The approach integrates critical perspectives on identity, social justice, and active citizenship with more traditional ESL concerns such as grammar, pronunciation, and second language literacy. It is suggested that under certain conditions, transformative or emancipatory practices can result when educators challenge received wisdom in areas of the syllabus not usually associated with critical theory. Three examples are offered from the author's classroom experience: discussion of principles underlying an upcoming referendum; student assessment that focuses on language awareness and media literacy; and conducting classroom research in the ESL context. (Contains 11 references.) (MSE)