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This study explores the use of creative journaling to help clients grapple with the existential questions that beset them at midlife in order to come to an understanding of how they want to live out the second half of their lives. It is a multiple case study involving 5 women from differing backgrounds. The women met once a week for ten weeks and were put through various semi-structured creative journaling activities that helped them to flesh out their past and present hurts, hopes and desires, and encouraged through the group process to confront and come to terms with those issues. At the end of the ten weeks, the participants were asked to give their feedback, both verbally and through journaling, about how the experience of creative journaling therapy personally affected them.