This document summarizes John Cook's 16 year research journey in learning technology from 2000 to 2009. It discusses two key projects: (1) Cooperative problem-seeking dialogues which explored how learners can work together to define problems, implemented in a system called MetaMuse. (2) A mobile learning project putting urban planning education in context using mobile phones to explore locations. It reflects that the focus remains on understanding how technology can support collaborative learning and adapting to learner contexts and goals.