In this research methods case study, I discuss some of the methodological choices I made and some of the challenges that I encountered while investigating how people organize the context of their activities in space and time. In this case study, I collected and analyzed video data to look at the organization of space and time during learning activities mediated by information and communication technologies (ICT). According to the qualitative approach I adopted, research designs have “built-in flexibility” allowing new and unexpected insights, leading to a growing sophistication of the design itself. This type of qualitative research is characterized by the progressive, non-linear development of theory and by the continuous interaction of theory and data throughout the process. Even though such non-linearity often constitutes an added value for qualitative research, it does not eliminate the need for a rigorous preliminary planning. I will use the example of the data collection and analysis of my case study to reflect on the delicate equilibrium between initial planning and flexibility of the research design in qualitative video analysis.