Background: Homelessness is rising in the United Kingdom, despite investment in measures to eradicate it made by the government and charity organisations. Aim: The aim is to examine the stories of homeless people in order to document their perceptions of their social status, the reasons that led to their homelessness, and propose a conceptual explanation. Method: We conducted 26 semi-structured interviews in three centres for homeless people in Cheshire, North West of England. Results: Three categories—education, employment, and health—emerged from the data and provided a theoretical explanation for the reasons that led to their homelessness. These are vital not only for the successful negotiation of one’s way out of homelessness, but also for achieving other social goods, including social connections, social mobility, and engaging in positive social relationships. Conclusion: Participants catalogued the adverse childhood experiences, which they believe limited their capacity to meaningfully engage with the social institution for social goods, such as education, social services, and institutions of employment. Since not all people who have misfortunes of poor education, poor health, and loss of job end up being homeless, we contend that a combination of these with multiple adverse childhood experiences may have weakened their resilience to traumatic life changes, such as loss of job and poor health.