“They stop you on the street. They know who you are,” Sheila Allen-Bell, assistant executive director of the Housing Authority of New Haven, said as she sat in her offices on Thursday, September 25. Allen-Bell was talking about New Haven’s homeless, some of whom had been stopping her in a desperate attempt to get a spot on the waitlist of the Housing Authority Haven (an organization that is also sometimes called Elm City Communities) for a home. Allen-Bell works to find safe housing for thousands of families throughout New Haven. But the people who stop her on the street? Sometimes, Allen-Bell can do nothing. Karen De Bois ’89, the director of the Housing Authority, added bluntly, “We can’t get everybody that needs to be housed, housed.”

For New Haven’s homeless, and the authorities that try to help them remove that label, capacity is the biggest roadblock. A complicated and ineffective system faces a stubborn pitfall: there is simply not enough space to get New Haven’s homeless population off the streets. The homeless men and women who approach Allen-Bell in 2014 may easily sit on waitlists for homes until 2020, and with this in mind, organizations around New Haven like Elm City Communities decided this summer to attack this stymied system head on. They wanted to show that their greatest impediment—capacity—was, in fact, surmountable. The 100-Day Challenge, which began on Wednesday, April 16, was the result of this decision. The results were salient and meaningful, the challenge a success; the question New Haven and its homeless face now is how— if at all —they can make that success last.

Accurately measuring the number of homeless individuals is difficult, as much of the data comes from shelters and transitional homes, which only count those who receive support and some form of housing. During 2011, The Connecticut Coalition to End Homelessness (CCEH), an advocacy group, counted 14,000 people who utilized Connecticut’s homeless shelters and transitional homes. They also tallied how many people were homeless in Connecticut on a single winter night: Tuesday, January 29, 2013. CCEH counted over 4,000 people across the state without a home, over 700 of whom were in New Haven. While sixty percent of these individuals slept in emergency shelters or transitional homes, forty percent slept on the streets.

For these homeless men, women, and all too often children, finding a stable home is not easy. The application process is long, decentralized, and data heavy—to tackle it is to hack through a forest of bureaucracy. Each building and housing facility has its own application and screening process. For instance, Leeway, a New Haven supportive housing facility for homeless individuals with HIV/AIDS, has an application that is three pages long and asks for medical information, insurance, and emergency contacts. The application for supported living programs at Continuum of Care, another New Haven organization that offers a variety of housing options for homeless individuals, is ten pages long and must be completed by a clinician, then approved by the Connecticut Mental Health Center before the applicant can be placed on a waiting list.

Difference in format and content of the applications aside, obtaining the proper information necessary to complete the forms becomes itself a significant burden. Applications in Connecticut typically ask for social security cards, birth certificates, and criminal records. Because finding clinicians, filling forms, and locating specific information can be difficult, individuals must usually rely on organizations and case management to move them through the system, a dependence that makes an already sluggish process even slower. Liberty Community Service, a New Haven organization that helps high risk individuals find homes, has a housing resource guide, which begins by advising individuals to “keep a paper trail. Make copies of all applications, ask for receipts, get it in writing, and write letters.” Beyond organizational savvy, successfully navigating the housing process takes serious persistence.

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Even when an application has been approved, only a spot on a very long waitlist—not a house—is guaranteed. De Bois estimates that there are over 10,000 individuals and families on Elm City’s waitlists. The waiting itself fluctuates wildly: depending on what kind of housing people are applying for, waitlists can vary from about two months in the fastest cases to seven years in the slowest. Lists for the elderly are more open, but only because the turnover rate is faster: put bluntly, the elderly do not live in their apartments for as long. The average wait for a home for a family remains a discouraging five to seven years.

For Joseph Jackson, now 64 years old, it was difficult to just get an application approved. Jackson had been homeless “off and on since ’96” and had a debilitating record. He had been arrested for domestic violence and had a long history of drug and alcohol addiction. And though he had not been convicted for anything since 1993, that history made it all but impossible for Jackson to secure a spot on a waitlist. His waitlist applications for Shelter Plus Care and Section 8 (the Housing Authority) were turned down. Many times, there was no personal interaction at all: Jackson would submit his application and hear back via letter that it had been rejected because of a background check.

Jackson’s addictions and struggles with waitlists left him close to death. He insisted he is surprised he is alive given some of the situations he found himself in during those eighteen years of homelessness. His family—he has a child, now 46, and four grandchildren — tried at times to support him, but was unable to help as much as he needed. What frustrated Jackson the most was the barrier his history had created for him. “The waitlists were ridiculous,” he complained. “I never had the opportunity…to show them that I had changed.”

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In February 2014, the leaders in the housing system for Connecticut came together to address the glaring inefficiencies in the system. The change began when Nadeem Matta received a call from Lisa Tepper Bates, executive director of the Connecticut Coalition to End Homelessness, an advocacy organization that attempts to address homelessness in Connecticut. Matta, the founder of Rapid Results Institute, a not-for-profit organization that helps communities around the world choose a project and carry it out in just 100 days, liked the idea. Matta said the “100 day idea comes out of observations and experiences that people tend to respond to a sense of urgency, a sense of excitement about accomplishing something, and a sense of possibility.” The Rapid Results model had already helped the homeless communities of Los Angeles and Nashville. Bates wanted to bring the model to New Haven.

The first step was to choose a goal for the challenge. On Wednesday, April 16, staffers from social service agencies; directors of local, state, and federal homelessness and housing agencies; front-line staffers who work daily with the homeless and leaders of New Haven organizations such as Columbus House, the New Haven Housing Authority, and Yale-New Haven Hospital came together for a two-day boot camp. After forty-eight hours of intense collaboration, they reached consensus on a goal: house 102 homeless individuals by Wednesday, July 30.

Though housing the 102 individuals was the tangible, empirical, goal, the underlying mission of the project, the Challenge went deeper: it was meant to entirely restructure New Haven’s housing system for the homeless. Matta said that the 100-Day Challenge “is not a program. It is a different way for the community to work that would employ the existing programs so that they can…connect the right resource with the right person with minimal of effort on the part of both parties.” To change the system, the leadership wanted to centralize it. They wanted to create a uniform entry-system that first targeted those who were most vulnerable, those “who were the most likely to die on the streets” if they remained there, Matta said.

And funding for the Challenge? There wasn’t much. The United Way of New Haven paid a small consulting fee to Rapid Results Institute for their expertise. The Yale Hunger and Homelessness Action Project (YHHAP), Yale University, and the Melville Charitable Trust contributed $25,000 to establish a Flex Fund for the challenge, money that could be used to help homeless move into homes by sponsoring bus fees, document fees, and move-in kits to provide furniture in the new homes, though there was no new funding for actual housing. Those involved with the challenge had volunteered to help out.

In order to make their goal a reality, the team first wanted to better understand the demographics of New Haven’s homeless population. They surveyed thousands of people, asking a variety of questions ranging from how long they had been homeless to their level of happiness, their health conditions, their substance use, and their criminal record. And while the volunteers scoured the streets, professionals at shelters, hospitals, and homeless service providers administered a standardized survey to any homeless individual who came through their doors.

In the second week of June, at the halfway point of the Challenge, nearly everyone was in a central database and organizations had consolidated the available housing options. Moving people into homes could now happen rapidly. The Challenge found homes for 102 of the 107 people it set out to house. As of Sunday, September 14, 43 had already moved into their apartments, and 59 were either getting documents ready or had a certificate and were looking for a new home. A process that once might have taken years was now happening in a matter of months. “Everybody had the passion to house these individuals to decrease and eliminate the chronic homeless in our community,” Lauren Castiglioni, a community matcher (someone who connects homeless individuals with housing opportunities) for the 100-Day Challenge and housing coordinator at New Haven Shelter Plus, noted. Many organizers said the 100-Day Challenge provided individuals with the much needed opportunity to come together and find impactful solutions within a difficult system.

Jackson, who said he has been homeless off and on since the mid-1990s, was living in New Haven when he was asked by a shelter to take a survey in August 2013. As the 100-Day Challenge formed months later, Jackson’s survey made it onto the list of hundreds of surveys conducted by volunteers. “Since then, they have been right by my side, working to get me a home,” Jackson said. Jackson was able to talk to officials face-to-face and tell his story. “I sat in front of a board and explained my issues to them, and what I was going through… They didn’t look at my past history,” Jackson said. Later that day, he got a call from his case management officer. He had been accepted onto the list for the Challenge. For the first time, his history had not kept him from moving closer to getting a home.

Volunteers working on the 100-Day Challenge helped Jackson complete the housing applications necessary to receive a voucher and gave him the contact, transportation, and support needed for him to find a new home. After that, Jackson was in charge. “It was up to me to go out and buy the apartment,” he said. “They really wanted me to do the work.” But when Jackson had trouble finding a landlord who would accept him and his troubled past—he also suffers from some health issues, a serious hip condition among them—the volunteers intervened and helped him find an apartment building that would take him and his voucher. Jackson now lives in West Haven and pays a portion of his rent each month from his Social Security check; the rest will continue to come from his voucher. “With the help that they give me,” maintained Jackson, “this [apartment] is forever.”

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It was the planning that happened months prior to the designated 100 days that allowed the challenge to be so successful. The New Haven housing authority put aside four vouchers specifically for the challenge. Liberty Community Services closed their waitlists in February 2014 to ensure there were houses available for the challenge. “Some new resources were coming down the pipeline anyway from the federal government and some from state government, so new units were put aside,” John Bradely, the executive director of Liberty Community Services, said. What made the program so successful was not just the increased efficiency of the application process and the collaboration between organizations but also the actual housing spaces made available on the other end. The challenge worked because the barrier of capacity was temporarily eliminated.

The energy and excitement that motivated people during the Challenge also allowed for some corners to be cut and steps to be skipped—moves that would be hard to implement in a long-term solution. Landlords of potential homes were notified in advance of the Challenge, which meant they were more lenient on their own screening processes and placed people into homes faster once they had their vouchers. In addition, some people were allowed to move through the system even if they didn’t have all the necessary information filled out in applications.

For their part, organizations devoted extra time and resources not normally available to make the process easier to maneuver. The Social Security administration’s officials in New Haven held special hours for those participating in the Challenge, Yale-New Haven Hospital had specific liaisons to help people obtain medical records, and the Connecticut Department of Motor Vehicles set up special early morning hours and waived fees for homeless individuals. The volunteers who worked on the Challenge, many in important administrative roles, did so “above and beyond their regular work activities,” said Kara Capone ‘03, Director of New Reach New Haven. However, that collaboration worked exactly because the project was so short term: it was not built to last.

The 100-Day Challenge ended in the final days of July 2014. As its glow fades, many of the problems that haunted authorities pre-challenge are resurfacing. Funds to keep volunteers and projects created especially for the challenge do not exist. Allen-Bell said she was unsure whether the community funding that the Housing Authority was trying to secure to keep some of the most important volunteers on staff would come. The leadership team created to extend the efforts of the 100-Day Challenge currently has no funding either. Though Matta maintains that the coordinated entry point the Challenge created is here for good, websites for New Haven housing organizations still have their individualized application. Waitlists for families at the Housing Authority have closed again. The extra office hours and resources to help those move quickly through the system have disappeared. Those who were not selected for the 100-Day Challenge still may have to wait years to be housed.

At the root of all this, unaddressed by the 100-Day Challenge, is the same barrier: capacity haunts New Haven’s housing teams. New Haven has the highest occupancy rate in the country: 98.6 percent of all available housing is occupied. (New York, notorious for its impossible prices, places second at 98.2 percent.) Although moving New Haven’s homeless away from the city is an option, the strategy runs into a similar problem: the cost of housing elsewhere is still too high. A person earning minimum wage in Connecticut must work two and a half full-time jobs to afford housing, according to Capone. That magnitude of a gap is not something New Haven’s homeless centers are equipped to bridge. With unnerving consistency, interviewees said that capacity remained the biggest problem they faced on a day-to-day basis. The 100-Day Challenge was never designed to strike at the root of the stagnancy that plagued New Haven’s system. Come September 2014, the city was faced once again with too many people waiting desperately for too few homes.

Now securely nestled in his new home, Jackson reflects on the problems that remain in the system post-Challenge. The biggest problem, in his mind, remains the long waitlists on which he was never able to secure a spot. “People give up on that [getting on wait lists] when it kind of gets tough. They don’t have any hope left,” he said.

Homelessness in New Haven is not new, but the urgency and energy to change it, made palpable in those 100 days, is. In the fall of 2004, the City of New Haven Homeless Advisory Commission released a Ten Year Plan to end chronic homelessness in New Haven. As Casavina Hall, Civic Director of United Way of Greater New Haven puts it, the plan was a “really big first step on how to end homelessness. Up to that point the plan was almost inconceivable.” That homelessness can be solved–not just mitigated and controlled–remains a relatively novel idea. If anything, the 100-Day Challenge is less a solution, more a byproduct of a greater push to aggressively address the problems in the homeless-to-home transition. Capacity remains the blockade, but for perhaps the first time, the homeless authorities in New Haven see it as removable. Hidden in their frustration is an implication that capacity can be addressed, that the system can be streamlined. Homelessness is no longer in need of Band-Aids, because there ought to be a cure. “The way that we’re doing things now in the homeless system,” Capone said. “Other parts of the country have done this—and it works.”