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Recently, various digital solutions have emerged to enhance the process of self-refection, which can be crucial for personal growth and resilience. However, whether technology can meaningfully match or augment a traditional approach like pen or paper remains to be ascertained. Our objective was to build an better understanding of design paradigms’ role in introspection. Through formative iterations, informed by Self-Determination Theory (SDT), we designed and developed diferent tool formulations (Analogue, Digital, and Hybrid) for comparison. Participants (N = 48) received one variant, completing a pre- and post-six-week assessment with the Self Refection and Insight Scale (SRIS) and intermediary self-reports for qualitative feedback. We found scores for Hybrid and Digital conditions change signifcantly, suggesting format decisions have meaningful impacts on the efcacy of designs to alter intrinsic motivation toward introspective behaviour. We also identify determinants and design considerations to help others conceive solutions to support or stimulate a component of broader well-being.