Online platforms like Reddit are increasingly becoming popular for individuals sharing personal experiences of leaving behind social, ideological, and political groups. Specifically, a series of "ex-" subreddits on Reddit allow users to recount their departures from commitments such as religious affiliations, manosphere communities, conspiracy theories or political beliefs, and lifestyle choices. Understanding the natural process through which users exit, especially from problematic groups such as conspiracy theory communities and the manosphere, can provide valuable insights for designing interventions targeting disengagement from harmful ideologies. This paper presents an in-depth exploration of 15K exit stories across 131 subreddits, focusing on five key areas: religion, manosphere, conspiracy theories, politics, and lifestyle. Using a transdisciplinary framework that incorporates theories from social psychology, organizational behavior, and violent extremism studies, this work identifies a range of factors contributing to disengagement. The results describe how disengagement from problematic groups, such as conspiracy theories and the manosphere, is a multi-faceted process that is qualitatively different than disengaging from more established social structures, such as religions or political ideologies. This research further highlights the need for moving beyond interventions that treat conspiracy theorizing solely as an information problem and contributes insights for future research focusing on offering mental health interventions and support in exit communities.