From Homeless to Homeowner: One Bay Area Woman's Journey

This summer, Jenn Oakley bought a one-bedroom condo in Emeryville — a milestone that once seemed impossible after more than a decade of homelessness, addiction, recovery and rehabilitation.

Her journey is wild, full of sharp turns and near collapses. Before I get to it, know this: When I first told her story as a San Francisco Chronicle columnist, readers sent money. Their generosity gave her the foothold she needed to start climbing back.

That’s the truth about touching the bottom: No one climbs out alone. Some land on a safety net. Others crash onto concrete. We pass them every day — in tents, in shacks, at stoplights with cardboard pleas.

Oakley’s story makes me wonder what else might be possible in the Bay Area, where stability feels impossible for many. Her story illuminates the cruelty of a system that punishes those who lose their housing. Years of homelessness, addiction and structural barriers made Oakley — the most determined unhoused person I’ve reported on — a long shot. She did nearly everything right — sobriety, training, work, service — and still needed luck and the kindness of strangers.

For the tens of thousands drifting street to street and the countless more hanging on by a rent check, the door to stable, permanent housing isn’t just closed — it’s bolted.

When I first met Oakley, she had her face buried in the hood of a beat-up Nissan Altima, which was leaking oil. It was May 2020, outside the Lake Merritt Tuff Sheds, Oakland’s transitional housing for the unhoused. It was the early pandemic, and most of us were going stir-crazy inside. I wanted to talk to the people who didn’t have the luxury.

Oakley told me she’d been homeless for a decade. After moving to Oakland from Tennessee nearly two decades ago, Oakley, a college graduate, sold insurance. Her slide began in 2009, after her father died. Grief pushed her into meth. The spiral was swift and merciless: she lost her housing, her work and nearly herself. Then came the stroke, which left her partially paralyzed in a room at the Value Inn at the corner of MacArthur Boulevard and Shafter Avenue.

I followed her for seven months. In December 2020, she moved into her own room near UC Berkeley — $950 a month for a chance at stability, made possible in part by the generosity of Chronicle readers. The distance between the streets and a bed with a roof came down to just $3,000.

On May 28, 2025, Oakley became the owner of a waterfront condo in Emeryville. The complex has gyms, jacuzzis and saunas.

“I’m working so much I can’t even enjoy it yet,” Oakley told me, standing in the breakfast nook where she has her work-from-home station. She’s juggling three jobs and nearly 80 hours a week. “In the future, I’m gonna make some changes to this place.”

She wants to get rid of the beige carpet. Oakley, who regularly runs five miles a day, still has to hang her running medals, patches and bibs.

We’ve kept in touch since meeting five years ago. The more I got to know her, the more I realized: If someone as focused as Oakley can barely grasp an affordable apartment, what hope remains for those on the street?

Gov. Gavin Newsom has pushed cities to ban homeless encampments across California.

RV communities are asphalt villages, stubborn and sprawling, their challenges mounting as more Californians trade driveways for curbsides and turn vehicles into permanent homes. California’s homeless population is still the largest in the country, with more than 187,000 people at last count.

In the Bay Area, the homelessness crisis continues to swell, reaching a record 38,891 people in 2024 — a 6% jump from the year before, according to the Bay Area Council Economic Institute. The surge is driven by the relentless housing and affordability crunch, compounded by struggles with mental health and substance use. Already stretched shelters and supportive housing programs struggle to keep up with a growing population.

For most, the odds of escaping homelessness are grim. But every so often, someone beats them.

Oakley, known as Tennessee Jenn on the streets, won the lottery. No, not like the unhoused man who won a $1 million prize from a California Lottery scratcher. Oakley won the housing lottery in Emeryville. She’s the first person to become a homeowner through First Home Emeryville, the city’s down payment assistance program for first-time buyers.

“If your credit’s not good enough, if you don’t have enough money, then you’re out,” she told me as she showed me around her place. “And even if you do get approved, then you gotta find a spot. There’s only 40 condos for sale in Emeryville at any given time.”

Only three were in her price range — and she needed to qualify for a loan. Another buyer made an offer, and she nearly lost the place, but her mortgage broker hustled to close the deal.

As we sat on her porch one Sunday afternoon last month, Fattie, Oakley’s lab-mastiff mix, nudged my leg, drooling for attention. Until her stroke, Oakley, now 47, had lived and worked in a hotel for three years, she said. The stroke only slowed her down temporarily. As she recovered, she threw herself into learning new trades, determined to build a stable future.

Oakley’s leadership and passion for helping others were obvious the first time she met former Oakland Mayor Libby Schaaf.

“It was a pleasure to stay in touch and see those gifts develop,” Schaaf said. “I’m grateful she stayed in touch with me. So often, as policymakers, we launch a program like Cabin Communities, we only get to evaluate its success with cold aggregated data or, sadly, not at all. To see intimately how Jenn was affected by the city’s actions was a profound gift for me. And I got a friend in the bargain.”

While living in the cabins, Oakley took automotive tech classes at Chabot College in Hayward. She completed a construction-training program at Rising Sun Center for Opportunity, which helps low-income people enter trades. She trained for two years to be a heavy equipment mechanic, only to be dismissed, she said, by a sexist instructor who questioned her age and mocked her background. Oakley said she was the third woman in 10 years to complete the program.

She’s worked security, changed oil at Jiffy Lube in Castro Valley, even fueled airplanes at San Francisco International Airport — until a background check flagged old drug and weapon charges, and she was escorted off the premises, she said.

She found her occupational calling by leaning into what she knows. She thrived working at Lifelong Medical Care, an organization that helps residents navigate the transition from homelessness into permanent housing.

“All these people had been homeless, now they’re trying to figure out how to live inside,” she told me. “They’ve got disabilities, addiction, violence — but I loved it. And they loved me. I was good at it.”

She’s now the lead case manager at Rising Sun, helping others move out of homelessness.

“I was homeless for 10 years. I was on drugs for 30. I can tell them all that stuff, and it gives me instant credibility,” she said.

Her compassion isn’t limited to her job description. She also looks after a man she met while homeless — a man who had a stroke and cannot speak. She helped him secure an apartment in Brooklyn Basin and still checks in, making sure he has meals, medication and the support he needs.

“We were friends, but we weren’t that close. He’s older, and I saw him, and I had instant survivor’s guilt,” Oakley said. “I mean, my stroke — I came back. I started taking care of him and doing his case work, doing all this stuff.”

On the weekends, she surveys unhoused people across East Oakland, where encampments have been pushed. She navigates streets to connect with people who would otherwise disappear.

“They’re scattered. It’s a whole different climate than it was five years ago. Ever since Grants Pass passed, everything has changed,” she said, referring to the Supreme Court decision that gives cities more power to regulate encampments on sidewalks and public property.

It’s a long way from the street to where she lives now, in a complex with Bay Bridge views and three swimming pools. We watched as neighbors shuffled past in robes, heading to swim or sunbathe.

“Like, wait,” Oakley said, shaking her head, “this is where I live now?”