A Local Woman Tells Her Story of Homelessness

A Local Woman Tells Her Story of

Originally printed in the Addison Independent, Thursday 11/21/2019
By: John Flowers

MIDDLEBURY — Skyla Jackson turned 19 last Thursday, Nov. 14. It’s an age at which her biggest worries should be navigating that first year of college or getting used to the demands of that first post-high-school job. Jackson would feel lucky if her anxiety was confined to cramming for a college test or becoming accustomed to a new workplace.

Instead, Jackson has already seen more upheaval in her personal life than some people will encounter during their lifetime.

It began around a year ago, when Jackson — who’s being treated for a depressive disorder and anxiety — left home. She believed she needed to strike out on her own in order to become a healthy, happy and positive adult. “I was arguing with my parents all the time, constant bickering,” she said. “I just felt like it was time for me to leave the nest. But I wasn’t really ready.”

She began couch-hopping at friends’ places before connecting in February with Anna Smith, an outreach worker with the Addison County Parent/Child Center (PCC). Jackson at the time was still a student at Mount Abraham Union High School and needed help with her studies. Her connection with the PCC gave her access to the center’s Elm Street housing in Middlebury for first-time renters. Jackson, still young and inexperienced with independent living, determined after five months that the Elm Street program wasn’t a good fit for her.

So she became a regular at the Charter House Coalition’s warming shelter on 27 North Pleasant St. in Middlebury, before moving into the John Graham Shelter in Vergennes a month ago. She said the John Graham Shelter offered her the best combination of food, lodging and a variety of wrap-around services — such as employment advice, counseling and housing search assistance — that will give her the best path to independence.

And while she calls the city shelter her temporary home, she maintains a strong relationship with the PCC. In August, Jackson began laying the foundation for her future when she enrolled in the center’s Learning Together program. The program offers intensive, 28-hour- per-week training that helps young people gain job readiness and other skills needed to prepare them as successful workers, parents and individuals. Participants like Jackson receive counseling, on-the-job training, schooling, prevention information and other tutelage.

Deirdre Kelly, the PCC’s education director, was pleased to report that Jackson has been earning above-average grades in her Learning Together studies. She’s also made a difference for the center, officials noted. Every weekday, Jackson takes the PCC bus from the Vergennes shelter to Middlebury. Those daily rides fortify her resolve to someday become an early childhood educator. “One of my favorite things to do on the van is sit in the back and read to the little kids,” she said.

Indeed, Jackson is not only learning at the PCC; she’s also teaching and finding out what it’s like to serve as a role model. A big part of her day involves caring for two- and three-year-olds at the center’s childcare job site. She beams as she expresses her love for the tots in her charge.

“I know what language to use with the kids,” she said. “I know how to speak to the kids so I’m not telling then ‘no’; I’m giving them direct instructions.” Donna Bailey, co-director of the PCC, said Jackson is a prime example of a person who’s
making a difference in spite of her current living situation. “I think what’s really important here is, Skyla is a very important part of our community,” Bailey said. “She helps, she’s a hard worker, she’s good with kids. I think that’s an
important thing for people to know; you can be a lot of great things, and be homeless.”


Jackson hopes to soon shed her homeless status. It’s a lonely and stressful way of life, dealing with uncertainties about food, clothing and other things that people take for granted. A restroom. A sink to fill a water bottle. An electrical outlet to charge a phone.

“I think we do need more resources, more bathrooms, more plug-ins,” said Jackson, who would often hang out at the town gazebo during her months at the Charter House’s warming shelter. “You could go to the library and plug your phone in, but it’s only open for a certain amount of time. What do you do for the two hours it’s not open? Are you just supposed to sit outside the library and do nothing? If you’re hanging out in the downtown, it’s hard to find the resources you need.”

Kelly and Bailey lamented the lack of such public amenities for homeless people in Middlebury. As recently reported by the Addison Independent, members of the town’s public safety committee have been debating the merits of extending more public services to homeless and transient individuals, a small number of whom have been taxing a shorthanded police force, according to town officials.

“What (Jackson) is talking about is basic human rights; they’re not asking for a widescreen TV or the most fancy things,” Kelly said. “She’s just asking for food, clothing and shelter. I want to be part of a town where we say, ‘We want to make sure everyone has that, no matter who you are, where you came from.’ I’d be proud to be part of a town where that’s a given.”


Jackson is proud to be weathering a difficult time in her life, and believes brighter days are ahead.

“It’s been an eye-opening experience,” Jackson said. “I’ve learned a lot about what it takes to take care of myself as a person and what it takes to take care of my mental health. It’s really hard. Taking care of myself is one of the hardest things I’ve learned to do. It took me a very long time to learn to take my meds regularly, go to appointments, get up in the morning and do what I needed to do.”

She believes the help she’s receiving from the PCC, the John Graham Shelter and counseling will help her unlock a door to a better life. Jackson is on target to pick up a key to that metaphorical door next June, in the form of a high school diploma from Mount Abraham Union High School.

Jackson hopes to be in permanent housing by the time she graduates. And help might be on the way to make that happen, as Bailey announced the PCC has been awarded a federal grant through the Vermont Runaway and Homeless Coalition that will create more vouchers for qualifying young adults to secure apartments.

“Skyla is definitely someone we’ll be working with,” Bailey said.

The big question is, will there be an affordable apartment vacancy for Jackson and the dozens of other low-income folks searching and hoping for a place to call their own.

“We don’t have enough housing, and when landlords have an opening — and we completely understand why — they tend to pick people who have experience, a work history, and a tenant history,” Bailey said. “It’s very difficult, especially for someone who is young and homeless, or who doesn’t have a lot of references and renting experience. And if you do have all of those things, we don’t have enough housing. We’re in a really tough spot as a community and as a state.”