The purpose of the study was to explore the experience of aging and approaching elderhood for five members of the Baby Boom generation with an emphasis on community, imaginal ways of knowing, and contemplative journaling practices. The research problem noted that Baby Boomers are attempting to transition into elderhood during a particularly challenging economic, environmental, and social moment, and asked: “How do these economic, environmental, and social crises affect Boomers’ experience of growing older and continuing contributions to society and community?” The research was conducted by engaging volunteer participants in focus group workshop sessions, and the narrative data collected was in the form of participant journals and transcripts of group discussion. The study employed a qualitative approach and offered a transformative framework for the narrative inquiry with its three embedded themes of environmental, economic, and equity crises. Data collection, analysis, and interpretation practices were based on ethnography and content analysis, and were performed in part with the assistance of focus group members. Validity checking was built into the design and consisted of crystallization and member-checking techniques. Study findings centered upon the struggle of reconciliation represented by oppositional forces residing within the data, the thematic structures, and the gargantuan crises that undergird the study.