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Few individuals have given careful thought to what their lives might be like after they retire. Although some may have considered the financial implications of living on a fixed or limited income, most have not considered the social and emotional impact of leaving work. Career practitioners can play an important role in facilitating the transition between work and retirement. This paper explores the common challenges and concerns faced by people entering this important stage of life and provides case examples from a variety of clients: some who are considering retirement, others who've chosen to fully retire, and a few who are enjoying a refreshing combination of less work and more leisure. (GCP)