This dissertation reports findings from a 10-month collaborative ethnographic study of discouraged workers in rural North Carolina. Methods including semi-structured and unstructured interviews, participant observation, and the Occupational Questionnaire were used to explore elements surrounding the daily occupations and situations of five discouraged workers. Findings address the formal classification, categorization, and conceptualization of 'discouraged workers' within the labor force; the idea of 'routine' as both a concept and concrete foundation for discouraged workers' occupations; and the extraordinary and multi-faceted nature of occupational possibilities in situations of long-term unemployment. These findings are discussed in light of cultural frameworks surrounding the opposition of 'crisis' and 'everyday' experience, and are couched in a Deweyan understanding of remaking tense situations. Conclusions include the need to incorporate experiential understandings when collecting data on discouraged workers; rethinking routine as an actively negotiated process that affects occupational engagement; and expanding ideas about what occupations are possible in experiences of long-term unemployment. Future lines of research related to well-being, social service processes, and discourse analysis are also discussed.