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Sherri

Working, Insured, and Still in Debt: One Woman’s Healthcare Reality

For Sherri*, a decade of public service came with more than just a paycheck—it came with a harsh education in the hidden fine print of medical benefits.

“I’d been a loyal employee, clocking in and out for years, giving my best—even when the best wasn’t always reciprocated,” Baltimore recalls. “But it wasn’t until year four that I truly understood what I was paying for.”

Like many of her colleagues, she’d defaulted to the standard health insurance plan. “Everyone else picked the ‘regular’ plan, so I did too,” she says. But the price tag? A staggering $266 every pay period just for the privilege of seeing a doctor—and the premiums kept rising, year after year.

Then came her lightbulb moment: switching to a High Deductible Plan (HDP) with a Health Savings Account (HSA). “That switch saved me so much money,” she says. Instead of funneling $266 to the insurance company every check, she paid $150 a month for the plan and deposited the difference into her HSA—money she controlled, with her employer adding a contribution. “It felt like a win. We’re a healthy family. Annual checkups, maybe urgent care once or twice a year. The HSA even helped cover dental work,” she explains, pausing to call out the shortcomings of dental insurance: “It’s basically a glorified discount card.”

But life, as Sherri puts it, “keeps lifing.”

The toll of sedentary work, stress, and a toxic workplace began manifesting in her health. “I started seeing orthopedics. I got poked, scanned, prodded,” she says.

Suspected sciatica, possible nerve damage, carpal tunnel—each diagnosis floated, yet dismissed as “not significant enough” for further care. “Apparently, unless you’re dying in five to seven business days, insurance just says, ‘Thoughts and prayers, sis.’”

Meanwhile, the bills piled up. Every doctor seemed to operate in a universe of hidden charges. “You go to the hospital, and two months later—surprise! Here’s a bill from someone you didn’t even realize was in the room,” Sherri says. “Oh, you spoke to the out-of-network toenail specialist for 35 seconds? That’ll be $500.”

Routine care wasn’t spared either. For three consecutive years, every mammogram flagged cysts. Each time: a biopsy, a six-month follow-up, and thousands of dollars in out-of-pocket costs—about $8,000 annually. Frustrated, her primary care doctor suggested switching providers. The new facility offered better care, more transparency, and fewer financial surprises. “I finally felt like a patient again—not just a walking invoice,” Sherri says.

But the financial burden remained. By 2025, she had accumulated over $20,000 in medical debt, while earning “just enough” to disqualify her from assistance—but not enough to feel secure.

“I grew up believing, ‘Work hard and you’ll be rewarded,’” Sherri reflects. “But it feels like the goalpost moves every time I get close. I’m working to pay bills, chasing side gigs to stay afloat, watching my health decline.”

Her story isn’t unique. It’s a familiar refrain for many Americans navigating an opaque, profit-driven healthcare system.

To others juggling similar struggles, Sherri offers this advice: “Check your benefits. Re- evaluate them often. Ask questions—even if HR gives you side-eye. Advocate for yourself. Switch plans if something feels off.”

Because in a system stacked against everyday people, survival means more than showing up—it means staying informed, empowered, and relentless.

Having medical debt adds layers of stress and directly affects the wellbeing of many families. Close to 100 million people in the U.S. have medical debt, and most cases of bankruptcy are due to medical debt. One essential step to limiting medical debt in Florida is for the state to expand Medicaid. Doing so would give 400,000 uninsured Floridians access to coverage. To learn more, see here.

 

*Sherri is a pseudonym used to protect the identity of the storyteller.

**Stock Photo

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