Canadian baby boomers began turning 65 – traditional retirement age – in 2011. How this generation perceives and experiences retirement may differ from preceding generations. In this online, grounded-theory study, 25 baby boomers who were approaching retirement or had recently retired participated in a multi-author blog about their retirement experiences and processes. We collected additional data via subsequent focus groups and participant interviews. Participants retired in several ways, including ceasing work, adopting casual or part-time work, and adopting new types of work. Findings highlighted three phases of the retirement transition: pre-retirement, characterized by both apprehension about retirement and idealization of the perfect retirement; the initial transition, which participants compared to an extended vacation, but in which they also struggled to adjust to increased amounts of free time; and mid-transition, when participants learned to balance structure and flexibility. Findings suggest that despite retirement transition challenges, many people have positive experiences with this transition.