How Job Loss, Expiring Benefits, and Rigid Assistance Systems Pushed One Woman to the Brink Even as She Did Everything ‘Right’
Sandra Gregston measures time by eligibility windows and waiting periods.
Once prompted, she spoke in long, continuous explanations, naming places, dollar amounts, notices, and rules—the language of someone who had learned to navigate systems long before she needed them herself.
Late August, when the 60-day notice arrived. Late September, when the three-day notice followed. October 20, when she handed over her key. And the days after, when she slept in her SUV while waiting to hear whether help would arrive in time.
For months, she was trying not to become homeless.
Gregston had been working full-time when her hours were cut from 40 a week to eight. By March 2024, she was laid off entirely. Unemployment benefits followed, but only temporarily. When they ended that summer, there was no immediate bridge to replace them.
At 49, she lived alone in a small granny flat in Perris, California. Her parents were deceased. She had no siblings to fall back on. A modest inheritance—stretched thin by years of pandemic disruption and job instability—ran out by early fall. Rent was due whether help arrived or not.
Even at the maximum benefit, unemployment topped out at $450 a week. It was an amount that exists cleanly in policy documents and far less cleanly in real life. Rent alone required more. The date her benefits ended was fixed. The months after were not.
Overqualified, Underqualified, and Running Out of Time
Sandra Gregston, whose housing became unstable after job loss and the expiration of unemployment benefits.
She searched for work the way people are told they should—within her field and far beyond it. Administrative roles. Project coordination. Anything that might turn into steady income. She tracked applications in a spreadsheet and kept 21 versions of her résumé, adjusting language to match the keywords employers’ software scans for.
“I’m told I’m overqualified for everything,” she said. “But I’m also told I’m underqualified for everything.”
She has an MBA but leaves it off her résumé unless a posting explicitly requires it. Entry-level roles asked for years of experience. Recruiters told her they only glanced at job titles, not descriptions. Standing work was no longer an option after a hip replacement and recurring bursitis.
The contradictions stacked up quietly, not dramatically.
When the 60-day notice arrived, Gregston began reaching out wherever she could. She called churches across the county—dozens of them—asking not for food, but for work or short-term help covering rent while she continued searching.
What she was offered instead were meals and referrals to sober-living facilities.
“I kept saying, ‘I don’t need food,’” she said. “‘I need a job. Or I need help paying rent.’”
Following the Rules, Losing the Housing
When eviction became unavoidable, Gregston followed the legal process carefully. She waited for the three-day notice, then for formal service. Legal aid helped her file a response. Assistance programs offered partial payments that arrived weeks late. She was always a month behind, never fully caught up.
By October 20, she had packed what she could, cleaned the unit, sold a few items, and turned in her key.
That night, she slept in her SUV.
The week she lived in her car was not chaotic. It was procedural.
She stayed near Temecula not because it offered safety or comfort, but because it offered something rarer: reliable, 24-hour access to a bathroom and a shower. A gym nearby stayed open overnight, and she built her nights around it—work out, shower, return to the parking lot, then go back inside again, sometimes several times, because access determined everything.
“I got a gym membership to go to the bathroom and take a shower,” she said.
Hunger was not the problem. Rest required vigilance. Privacy existed only in increments.
What was missing were bathrooms—and the recognition that unhoused people still have ordinary physical needs.
“People want to fund food,” she said. “They don’t want to fund what people actually need.”
She bought thermal pants and a beanie to sleep through cold nights. After several days sitting upright in the driver’s seat, she cleared space in the back so she could lie down. She locked her doors. She kept her routine tight. During the day, she ran errands, applied for jobs, and took calls. At night, she returned to the parking lot.
A week later, someone from her spiritual community offered her a temporary place to stay. She moved in quietly, grateful for the stability but aware of its limits. She had access to a bed, a shower, and a small section of a refrigerator. Her belongings remained in storage—an expense she could not sustain much longer.
Gregston does not describe her experience as a collapse so much as a narrowing. Options closed quietly. Distance mattered. Traffic mattered. Geography mattered.
When Help is Predefined and Misaligned
People kept telling her to call 211, California’s free information-and-referral line for local services. She did. Repeatedly.
The questions were often the same: Was she disabled? Over 55? A veteran? A parent? Experiencing domestic violence? None applied. The call ended with another referral that led nowhere.
People offered food. Or treatment. Or help defined in advance.
“They don’t want to ask, ‘What do you need right now?’” she said. “So, people think I need food. Or that I’m a drug addict. Or mentally ill. They decide for you—but they don’t want to help you on your terms.”
Gregston’s experience mirrors a growing category of people slipping toward homelessness not through crisis or addiction, but through job loss, expiring benefits, and assistance systems calibrated for emergencies rather than transitions. For people who do not fit neatly into eligibility boxes—too young, too healthy, too “functional”—help often arrives late. By the time it does, stability has begun to unravel.
She spoke plainly about the systems she encountered—unemployment benefits that expired before wages returned, general assistance capped at three months, and referral lines that sorted callers into categories she did not fit.
Gregston speaks with precision about what she wants people to understand about homelessness. She describes it not as a single moment, but as a process—marked by delays, misaligned systems, and circumstances shaped less by personal failure than by timing, health, and access.
Her clarity comes, in part, from experience. Years earlier, she worked in an office serving unhoused people, where she saw firsthand how easily stability could unravel—and how little the public understood what people actually need to survive.
What Homelessness Actually Takes Away
Assistance, she learned, often centers on what is visible. Food. Clothing. Temporary relief. What goes overlooked are the documents and infrastructure required to exit homelessness at all: access to bathrooms, secure places to store belongings, and safe ways to protect identification—birth certificates, Social Security cards, driver’s licenses—documents routinely lost during sweeps and nearly impossible to replace without stability.
“They don’t need just food,” she said. “They need dignity.”
She is 50 now.
When she imagines the next chapter of her life, the answer comes easily.
Full-time work. A desk job she can physically manage. Training toward a Six Sigma certification. Independence restored slowly and deliberately. Renting. Paying bills. The possibility—distant but intact—of homeownership.
It is not a fantasy. It is a plan.
For now, the plan exists alongside uncertainty. She continues applying. She continues waiting. She continues navigating the narrow space between assistance programs and employment systems that rarely move at the same speed.
Homelessness, in her telling, was not the absence of effort. It was the consequence of trying to survive within systems where help arrives in fragments—never quite enough, never quite on time.