While not asked about this directly, most of the interviewees in this program were chronically homeless at one point. One even saw himself as being homeless in the future. Our conversations alluded to the cycle of homelessness and how hard it is to break free from the cycle. Evette talked about how easy it was to get stuck in the cycle of homelessness:
A lot of homeless people, they go and rent hotel rooms to get off the street just to have a place to sleep, just to have a place to eat. But then it uses up their money so fast that they don’t – they don’t even get a chance to be stable. And then you have programs, like I was outside and there was a program that had opened and all this homeless people had got rooms. But they didn’t have jobs to maintain them. They lied their way into it. “Oh yeah, I get a check every month.” Because they had a couple dollars in their pockets so the landlord would go ahead on and take the stipend that the government, or that the state, or the federal, local government was giving them for that person without that person having a way to sustain their self. So then what happens? They go right back out on the streets again within ninety days. It’s a vicious cycle and the only way to pull yourself up out of it, to maintain stability, is to really want it. And after you stay outside for a couple years, you don’t want it anymore – you just get used to it. You – those people become your family, they become your friends, they become your enablers – they enable you to stay outside.
This detailed description of the desperation that people go through to find housing, only to lose that housing and struggle with chronic homelessness shows how difficult it can be to break the cycle when an individual is in distress about their situation and has received a lot of previous disappointment. As Evette relates above, she feels that some homeless are forced into such desperate situations that they feel the need to lie and cheat the system to attempt to better their situation, only for it to be made worse in the long run due to temporary solutions.
In their book, At Home on the Streets, Wasserman and Clair discuss the struggle to break free from the cycle especially when the health care system or criminal justice system is involved.
The health-care and criminal justice systems become increasingly problematic obstacles once an individual becomes homeless, since contact with them becomes more frequent. Individuals who are homeless are more likely to become sick as a result of their living conditions or injured because of the type of work the perform. Exacerbating the later, the informal nature of their employment leaves those who are homeless little recourse for work-related injuries. They are also more likely to be arrested for misdemeanor crimes such as vagrancy, because they are forced to do private things in public spaces. Since they are often unable to pay the fines for these arrests, they accumulate debt in the court system. 
This quote reveals how circular the problem of homelessness really is. As the authors discuss, a person often becomes homeless after a living a life on the brink of poverty and losing their job. Once they lose their job, they lose health care and the ability to pay for their house and car. When they cannot pay for those things, many end up homeless. This sudden thrust into homelessness can lead to severe depression or the exacerbation of the symptoms of a current mental condition like schizophrenia. Because they have no access to health-care, many chose to self-medicate with drugs and alcohol, thus hindering their ability to find new stable employment or keep up with family ties and leaving them to find work through a temp agency or manual labor. Once a person has entered this ‘revolving door’ of homelessness, escape can prove very difficult, as the obstacles seem to become more insurmountable the longer one is homeless. But despite of circular set of obstacles, the participants of Wasserman and Clair’s study “[saw] their lives on a course: one switch sent them into homelessness and another in the future will take them out of it.” While Harold sees himself as heading “back to [his] tent” in the future should things not go his way, other interviewees see themselves as having broken free from the cycle at this point in their lives. This shows that these people remain optimistic on exiting homelessness despite the many obstacles they may face.
Interviewees for this project and in the study conducted by Wasserman and Clair all talked about having very negative feelings about the shelter environment because it was dirty, dangerous, and made them feel like complete degenerates because many of the shelter programs “conceptualized homelessness as an addiction problem.”  For most of these men, addiction is not the reason they are homeless. It is something that some, not all, use to cope with their situation and therefore they do not want to be labeled as a homeless addict, because that definition is so narrow, confining, and full of negative connotations. While the shelter assistance programs can be very useful for getting off the streets, there is a barrier to entry caused by the imposed identity that all homeless are addicts or mentally ill. People struggle asking for help to begin with because it hurts their pride and sense of masculinity, but it takes an even bigger hit on one’s pride and self-esteem when asking for help also means acknowledging and taking on a stigmatized identity as your own.
 Lewis, Evette. Interviewed by Kelsey Glander. Richmond. Video. March 16, 2016.
 Wasserman. At Home on the Street, 80.
 Wasserman. At Home on the Street, 80.
 Ibid., 78.
 Ibid., 100.
 Smith, Harold. Interviewed by Kelsey Glander. Video. Richmond. March 15, 2016.
 Wasserman. At Home on the Street, 115.