This workshop explores potential connections between life experiences, resource accumulation, and technology attitudes across different generational cohorts. Building on prior work, we propose considering age as an axis for accumulating (or not decumulating) various resources which impact their technology engagement in later life. Through activities such as timeline creation and technology attitude mapping, participants will gain insights into shared patterns and unique narratives within their generations. By fostering empathy and understanding, the workshop enhances HCI research and design practices.