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Recent research has started to explore more flexible, manual self-tracking systems, which allow users to express themselves through their data and learn by engaging with their experiences in-the-moment. This article describes a field trial using the Chromatize app, designed to explore the value of minimalism and flexibility \u2014 including in data histories \u2014 in personal tracking systems. Our data indicate that low-burden experience logging systems which focus on the creation of symbolically-rich, self-defined data can support self-awareness, reflection and regulation at opportune moments. 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