This article describes our transitions through three phases of a reflective cycle as a journey from the past to the future. In the descriptive phase, we delve into our past research experiences and address questions such as: What is the role of mathematics at work? In doing so, we uncovered additional venues for exploration that called for a new mode of analysis. We transition into a theory-building phase where we share our learning experiences that occurred in-the-moment. We then shift to an action oriented (reflexive) phase during which we construe personal practical theories that enable us to negotiate broader understandings of the role of mathematics at work and identify areas for future inquiry. We document our lived experiences as informed and inspired by our work with two groups of workers--bus conductors and street vendors.