This paper explores the significance of designing online learning led by the principle of direct and meaningful participant engagement. It considers the notion of kindness as a crucial value contributing to pedagogy and the development of meaningful learning relationships. The paper challenges the "delivery" approach to online learning, suggesting that the flexible and explicit design of engagement opportunities from a sociocultural perspective is a more meaningful and human approach to learning online. The paper clarifies the term Digitally Mediated Learning (DML) to establish connections to important pedagogic positions. The research approach is based around a qualitative professional reflective enquiry. It considers the experiences of learners on a Masters in Education online module and concludes that design, engagement nurturing, community cohesion and kindness can become crucial aspects of successful DML, if institutions learn to value the life projects of others more fully.