We investigated the interplay between the personality trait exploration and objective socioecological conditions in shaping individual differences in the experience of two individual‐level benefits of current social change: new lifestyle options, which arise from the societal trend toward individualization, and new learning opportunities, which accrue from the societal trend toward lifelong learning. We hypothesized that people with higher trait exploration experience a greater increase in lifestyle options and learning opportunities––but more so in social ecologies in which individualization and lifelong learning are stronger, thus offering greater latitude for exploring the benefits of these trends. We employed structural equation modeling in two parallel adult samples from Germany (N = 2,448) and Poland (N = 2,571), using regional divorce rates as a proxy for individualization and Internet domain registration rates as a proxy for lifelong learning. Higher exploration was related to a greater perceived increase in lifestyle options and in learning opportunities over the past 5 years. These associations were stronger in regions in which the trends toward individualization and lifelong learning, respectively, were more prominent. Individuals higher in exploration are better equipped to reap the benefits of current social change––but the effects of exploration are bounded by the conditions in the social ecology.