With midlife career transitions becoming more common, and colleges and universities needing to replace retiring faculty members, more professionals who have attained doctoral degrees may be transitioning to a second career in the academy. While their practitioner-based knowledge and leadership skills might be welcomed, especially in applied degree programs, they could face unanticipated challenges, as may their new colleagues. Themes that arose from reflective sessions between two such new faculty members and a mentoring colleague are shared, along with recommendations for those considering such a transition, their new campus colleagues and for faculty developers and administrators.