This thesis explores the challenge of preaching that encourages listeners to embrace transition as an invaluable part of a healthy spiritual life. It builds on the work of William Bridges who argues that healthy transition requires intentionally letting go of a previously familiar place; remaining in a place of uncertainty and possibility while important internal work unfolds; and gradually taking hold of new clarity and direction that begins to emerge. The primary ministry context is a Unitarian Universalist congregation marked by significant religious diversity, as well as a high percentage of members who have come to Unitarian Universalism from other religious and non-religious backgrounds. The claim of this thesis is that there are methods and elements of preaching that communicate effectively to listeners in spiritual transition. Drawing on the work of Leonora Tubbs Tisdale and Robert Stephen Reid, it encourages preaching that is indeterminate in approach; pays particular attention to the intuitive and emotive aspects of preaching; and understands the significance of ethos in preaching.