For three days in early January, with camera and microphone in hand, we embarked on a project to document people’s experiences of standing on the median or along the street with cardboard signs.

The practice, which is called “flying a sign,” is an issue of intense debate in Portland and beyond. We wanted to know what motivated people to fly signs, what they used the money for and what they did on a day-to-day basis to survive. We interviewed 10 people, and here is what we learned:

Most of the people who fly signs said they would rather work than beg for money.

In conversations with signers on the median or along the street, we learned that all of them want to be working. Some have experience as general laborers, boat builders, masons. Others worked in food service. Some were disabled, had criminal records or lacked housing, which affected their ability to work.

 Most of the people we talked to said that flying a sign was humiliating.

The experience of standing on the median or sidewalk with a cardboard sign and asking for money is a degrading one. When we asked them “Have you ever had to ask for money?” most of the people on the street said they had, and that it was hard. During the interviews, we heard passers-by yelling “Get a job!” which only adds to the humiliation.

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One person we interviewed said, “Every time someone passes by, I lose a part of my soul, and every time someone gives me something, I lose even more.” Another person said, “I don’t like to do this – I know I am taking money from working people.”

Most people said they use the money to buy essentials.

Only one of the people whom we interviewed said they would buy a beer with the money. The rest said they use the money for food and water. Were they lying about that? We doubt it.

Most talked about very specific things they use the money for. One person said, “I know it’s not essential, but I would like to be able to have creamer for my coffee once in a while.” Another said, “I use the money to bribe my way into a friend’s home for the night by paying for food, so I don’t have to sleep outside.”

Of the 10 people we interviewed who were flying a sign, five live outside in tents or in the woods.

The first day when we collected interviews, the temperature was in the single digits and breezy. Living outside in the winter in Maine is hard. Enough said.

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Almost all of them are from Portland.

While the people we talked to have lived in other places at some point in their lives, nine out of the 10 have lived in Portland for many years.

They all have a story.

Many of them spoke about being judged, and wished that people would stop and talk to them about how they ended up on the median. “But,” one man relented, “nobody wants to hear it – it’s too depressing.”

It’s not just about money.

Flying in the face of cynicism, all of the signers spoke of the social interactions that occur while on the street, and how they look forward to positive encounters. One gentleman laid it down by stating, “If someone wants to give money, that’s fine. If they want to give me something to eat, that’s great. If they want to talk, that’s even better, because I don’t have many opportunities to have intelligent conversation.”

There are many homeless and extremely poor residents of Portland who do not fly a sign, and it is quite possible to get “three hots and a cot” for free through Preble Street and the Oxford Street Shelter. So why do some choose to do it? Perhaps it is that by earning some pocket money, and having the choice to buy a sandwich or creamer or even a beer, these folks are asserting a sliver of autonomy and grasping onto a sense of self that is threatened daily by the anonymous nature of homelessness.


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