While most people usually tend to avoid thinking about their death, it can be beneficial to reflect on it. As technology is further integrated in our lives, HCI needs to consider that users eventually die. A concrete example for this concern is digital legacy. From a perspective of existential HCI and Thanatosensitivity, this thesis explores how young adults experience their own mortality and how they might be encouraged to reflect on their lives by engaging in their digital legacy. Subsequently, this exploration led to conducting expert interviews, sending out cultural probes, and sharing a collaborative matrix. Synthesizing and ideating on the gathered material concluded in a low-fidelity prototype that was tested by six users. The initial user feedback and individual workshops with three participants led to further explorations in the form of two workshops – one for ideation, the other for analysis. The thesis concludes in a series of conceptual design proposals that act as ground for discussion with implications for design opportunities and future research alongside an analysis of key findings.