The aim of this research is to discuss how the digital leisure experiences of different generations differ and converge in terms of personal enrichment. The concept of personal enrichment signifies a paradigm that transcends the conventional understanding of leisure, which has historically been conceptualized as consumerist, passive, and distinct from income-generating activities. In contrast, it emphasizes development, active engagement, and, in some cases, the potential for income generation. Semi-structured in-depth interviews were conducted with 32 people, eight from each generation (Baby Boomers, Generation X, Generation Y, and Generation Z), living in Konya, Turkey. Digital leisure was associated with personal enrichment, which was divided into three categories: practical, material, and cultural gains. Generation BB and Generation X appear more interested in practical gains (learning through hobbies) and cultural gains (such as general culture). Generation Y is engaged in all types of gains, while Generation Z shows greater interest in material gains. BB and X generally do not view digital leisure as a source of income (material dimension). Compared to all groups, the digital leisure experiences of Generation Y align more closely with the historical ideal of leisure.