People are often limited to their own perspectives, which are deeply shaped by their surroundings. Place – that is, the geographic location in which people live and interact with one another – is enriched by historical, cultural, and social contexts which subsequently influences how people think and behave. People often perceive locations, especially unfamiliar ones, as inherently distinct from the self, merely as places to visit and learn about rather than as mechanisms for personal development. Yet, people’s internal worlds are shaped by the same forces which shape surroundings. Individual habits, beliefs, values, and attitudes evolve through exposure to societal, cultural, and environmental pressures. Whether consciously or subconsciously, people make efforts to improve self-concept and overcome personal challenges through reflection, self-awareness, and seeing issues from a new perspective. Oftentimes, it is the last element that enables the first two to occur. There is an opportunity to reconcile people’s internal worlds with their external world, particularly through providing people with contexts that are disparate from their own. In this manner, we welcome alternative perspectives, grounded by physical locations, to help individuals reveal current thought patterns, make comparisons, and ultimately gain personal insights. In this paper, we present WorldMirror, a system that uses a mixture of LLM discussions and interaction with videos to help users gain a deeper understanding of their problem, learn different ways to approach their problem, and learn about the world. Given a user problem, the LLM prompts the user to learn more about their problem and connect it with different aspects of the user’s life to identify underlying root causes. Then the LLM provides locations around the world that can teach the user new ways of thinking about their problem. Through interacting with a video of people living their daily lives at the location and further discussion with the LLM, the system pushes users to learn more about their problem and the world. A preliminary study with one participant using the system suggests that WorldMirror can understand the user’s problem thoroughly and identify root causes but struggles to help users grow in their own thinking about their problem and the world.