This document outlines an educator's experience transitioning from a traditional education model to an Education 2.0 model that incorporates more collaborative and flexible learning using web 2.0 tools. It discusses opposing views around structured vs flexible learning and top-down vs bottom-up approaches. The educator describes implementing wiki, blogs, microblogging and other web 2.0 tools in their courses and the benefits of less lectures and more student-centered collaborative work, but also challenges around information dispersion, digital competency, and privacy issues. The conclusion advocates for Education 2.0 as more than just adding technology, and identifying individual learner needs.