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In this article, the author suggests midcareer is a central but transitional season in a Christian leaders’ life-course. During this season, the Lord seeks to bring clarity to, and integration between, the leader's calling as a citizen of the Kingdom of God, the leader’s personal identity as united with Christ, and the leader’s occupation within his or her organization. After proposing a conceptual framework for the experience of midcareer, the author discusses common themes, challenges, and opportunities of “middlescence” (Morison, Erikson, & Dychtwald, 2006), which exist on a continuum from “burning out” on one end to the “sweet spot” of ministry on the other. This article concludes by proposing a series of developmental assignments midcareer Christians could employ as they move toward fruitfulness.