Reflective professional development results from thoughtful planning of goals and meeting learning objectives. With rapid changes in health care resulting in major reevaluation and even modification of the role and functions of an occupational therapy practitioner, producing a historical record of competencies in order to learn from one’s own experience and to plan for change is essential. A new use of the portfolio is presented to show that a portfolio can be more than the typical repository of completed projects. The transitional portfolio is introduced as a tool for one to self direct professional development through thoughtful engagement with artifacts created during one’s career in relationship to professional goals and desired roles. The transitional portfolio process is holistic, flexible, and reflective. It can serve as a way to document accumulated knowledge and skill acquisition as well as facilitate thoughtful, planned reflection on one’s career development in occupational therapy. This article describes the use of transitional portfolios to connect professional development learning experiences, accomplishments, and future opportunities for occupational therapy practitioners.