The career arc for many in student affairs involves an uncertain journey. Finding balance between the professional and personal life can be challenging. For some, changing careers in mid-stream, an emerging trend in some facets of the American working landscape, offers possibilities. For others, retiring after a full career and working part-time in another is becoming a financial necessity; however, combining the two, changing career directions after a full professional life without retiring, is different. This article reflects the experience of one, the author, a senior career student affairs administrator turned faculty member, and explores his own professional journey--the accidents, coincidences and choices that merged into this journey of career change. It is the story of a road less traveled but one certainly worth consideration in the long arc of professional life.