We examine how neurodivergent individuals experience creating, interacting with, and reflecting on personal data about masking. Although self-tracking is often framed as enabling self-insight, this is rarely our experience as neurodivergent individuals and researchers. To better understand this disconnect, we conducted a two-phase qualitative study. First, a workshop where six participants with autism and/or ADHD crafted visual representations of masking experiences. Then, three participants continued by designing and using personalized self-tracking focused on unmasking over two weeks. Using reflexive thematic analysis of activities and interviews, we find that self-tracking imposes substantial interpretive and emotional demands, shaped by context-dependencies that challenge assumptions in self-tracking. We also find that facilitated sharing of experiences might validate emotional responses and support reflection. We identify three emotional dimensions that shape engagement with personal data in a working model of emotion in self-tracking, and discuss implications for designing self-tracking and reflective practices that incorporate peer support and better account for context and emotional labor.