Many youth experiencing homelessness (YEH) are surprisingly hopeful. We propose a typology of the hopes for the future (HFTF) of YEH, based on a qualitative study employing grounded theory. YEH fell into four categories: (a) nonmainstream HFTF youth who wished to escape the mainstream, (b) mainstream HFTF youth who wished to integrate into the mainstream, (c) marijuana-economy HFTF youth who aspired to escape homelessness by entering the marijuana economy, and (d) no HFTF youth who did not or could not envision the future. Our finding that some YEH transition between different HFTF suggests a modifiable point of intervention. We share novel findings regarding how the perceived trajectories of some YEH may have been influenced by the evolving legal status of marijuana. Our emic approach to constructing a typology may inform the design of more acceptable/effective interventions. We suggest implications, including ethical quandaries, raised by our findings.