Instructional designers often navigate ambiguity in their professional journeys towards performance improvement. Although there are many similarities between the two professions, there are also important differences. Most notable is that instructional designers tend to focus on learning-based solutions, while performance improvement practitioners take a broader approach that may include training as just one aspect of their proposal in solving a business problem. This study explores the experiences of professionals who successfully adopted this broader approach and, through their stories, seeks to understand what made the transition successful. Their journeys were captured using an adapted version of Robert Atkinson’s life story interview technique, and the data was analyzed using Kathy Charmaz’s constructivist grounded methodology. The result was a selection of four emergent themes. These emergent themes and their underlying categories led to a model that captured the ambiguous ID-to-PI transition. This model suggests three immediate actions that serve as a guidebook for instructional designers seeking to move into performance improvement. These actions are: (1) Build a collection of performance stories, (2) Be an active member in a performance-focused professional organization, such as the International Society of Performance Improvement, and (3) Find your performance lens to see the world. This model is then simplified to resemble Carl Binder’s Performance Chain®. Finally, the ID-to-PI career transition is mapped out with Binder’s Performance Chain® and Six Boxes® for business results, work outputs, behaviours and behaviour influences in hopes of making the journey from ID to PI less ambiguous. Keywords: Performance Improvement, Instructional System Design, Instructional Design, ID-to-PI career transition, ISPI, Charmaz, and Constructivist Grounded Theory