Not every child would be excited to work on their reading or math skills, but the one-on-one learning session with Kurpiewski is the highlight of Jayden's week. In fact, she wants to spend more time on it, her mother Anestha Richardson, 44, says.
"She tells me, 'Mommy, can I do more?'" Richardson said. "Jayden is loving it like crazy. She's come so far."
The family moved to Pittsburgh about a year ago from Fort Lauderdale, after increased rent imposed by a Section 8 landlord became unmanageable. So much so that it forced the mom, who was working in health care, and her young daughter into homelessness.
Getting by was difficult, and Jayden missed a chunk of second and third grade. Richardson doesn't like to dwell on what happened during that time. Rather, she's focused on getting Jayden where she needs to be in school.
"Education is more important than anything else," Richardson said.
Help now arrives in the form of a flashy bright blue van, marked "Winnie's Wagon," on their street each Tuesday. Inside is a mobile classroom, equipped with learning tools, games and books designed to provide kids like Jayden the individualized academic support they need.
Winnie's Wagon first hit the road last November, aiming to create better futures for young people facing the challenges of homelessness. It is the only mobile classroom in southwestern Pennsylvania serving the homeless student population, which has dramatically increased since the pandemic.
The flexibility of the Mobile Learning Program furthers the reach of schools into the community by bringing education support directly to students.
"Homeless children face significant educational challenges, including missed school," Kurpiewski said. "These kids need targeted education and support programs. Winnie's Wagon addresses the immediate crisis of homelessness while also thinking about the long-term effects on a child."
Just last month, the Homeless Children's Education Fund received nearly $640,000 through the Pennsylvania Commission on Crime and Delinquency Violence Intervention and Prevention grant to expand the programming.
The funds will allow HCEF to create a second mobile classroom program, Winnie's STEAM Machine, to focus on science, technology, engineering, arts and mathematics. A mobile learning coordinator with expertise in STEAM education will also join the team, AJ Jefferson, the organization's executive director, said.
"As soon as you walk in, it's going to be very technologically focused," Jefferson said. "My vision is to have smart boards, a lab, and all these other great things in order to make those career paths accessible and practical to our students."
While the idea of homelessness often conjures images of encampments and life on the street, that's not what is mostly commonly experienced, especially for families, said Kurpiewski. Often, people are "doubled up," which refers to temporary shared living situations with friends or family that happen due to loss of one's own housing or economic hardship.
It's a kind of homelessness that leaves families on edge, never knowing when the stay is overwelcomed.
That was the case for the Richardsons, who left Florida to stay with a family member. The situation was fraught. Jayden often told her mother that she felt uncomfortable there. She clung onto Kurpiewski too, pleading with her not to leave after sessions.
This was months before the launch of Winnie's Wagon, so conducting the tutoring wasn't easy either. Kurpiewski met Jayden at a local library because she wasn't allowed inside the home.
"A lot of times, in those situations, the families aren't always keen on letting us in to provide in-house tutoring," Kurpiewski said.
Because Jayden's circumstances were escalating, Homeless Children's Education Fund staff helped them find their current apartment in Northview Heights, a 450-apartment community run by the city's housing authority.
Housing brings a level of much-needed stability to a family, but children still feel the effects of what they experienced long afterwards.
"Just because you have a home now doesn't mean you're academically caught up and the trauma doesn't exist," Kurpiewski said. "A lot of times, the mental and emotional trauma that goes with it, along with the missed school, tends to stay with them throughout their childhood, and even into adulthood. We do our best to try to mitigate that."
Chronic absence has long been a crisis among the homeless student population, but the pandemic proved to exacerbate the problem, said Brian Knight, community engagement manager for the HCEF.
State data shows that almost 60 percent of homeless students in Pennsylvania were chronically absent during the 2021-2022 school year. For the total population, the number of chronic absences drops to about 25 percent. The gap was just as dismal in Pittsburgh Public Schools, where nearly 75 percent of the homeless student population were chronically absent, compared to just under 45 percent for the total student population.
The reasons children experiencing homelessness miss school so much are vast, Knight says. It can be a lack of documentation to meet enrollment requirements; high mobility that interrupts regular school attendance; lack of transportation; lack of supplies; poor health, fatigue, hunger and mental health issues.
Even when they have a roof over their heads in a doubled-up situation, kids can still be bouncing from place to place. Every time a child moves, three to six months of their education is lost, research shows. This makes homeless children four times more likely to show delayed development, and two times more likely to have learning disabilities.
During the earlier academic years, the missed class time is particularly devastating to their academic progress.
"That's a really critical time for your development, for your ability to read," Knight said.
Richardson tried to help her daughter with her schoolwork. But without a support system or the right resources, Jayden was still falling behind. It left them both frustrated. That's why she says there was no hesitation to join the mobile learning program when a social worker at Jayden's school, Pittsburgh King PreK-8 on the North Side, recommended it.
"It was either I get the help for her or she keeps struggling," she said. "I was excited to get the program because Jayden was excited."
The HCEF advocated for Jayden to get an individualized education program, or IEP, through her school. She is working hard to reach grade level milestones for reading and math, reaching all her IEP goals so far.
"When we started, she had a very difficult time even reading the simplest CVC words — consonant, vowel, consonant — cat, dog, that kind of thing," Kurpiewski said.
Now, Jayden is close to finishing Bob Books, a children's series designed to teach phonics-based reading skills. Each level addresses a single stage in reading development.
"I think she has two more books left, then she'll officially graduate from Bob Books, and I'm very excited," she said.
During a session last week, Jayden sat on a bench inside the van, parked in a cul-de-sac, with a smile rarely leaving her face. She mastered long vowels, like "ee" with a reimagined version of dominos, which asked her to use the tiles to fill in missing parts of words.
Another activity challenged her to solve math equations on flashcards. They finished out the session with coloring a bookmark, where Jayden revealed her favorite color is red.
In getting to know the families, Kurpiewski sees how much parents want their children to succeed.
"A lot of our families that we work with are very involved with their kids, they want what's best for the kids," she said. "Mom would do anything for her, for Jayden."
Like always, Jayden squeezed her tutor with a big hug before she left for the day.
"She did good?" Richardson asked, handing over a freshly cooked fish and rice dinner for Kurpiewski to take home, a small gesture she makes often to share her gratitude.
"Yes, she did good," Kurpiewski responded.
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