The conventional wisdom says that if you earn enough money, the healthcare system’s rough edges won’t cut you. That if you’re a professional with a good income, prescription costs are an annoyance — not a genuine crisis. Gladys Okonkwo’s year proved that wrong in three separate ways, and she’s still paying for it.
I first came across Gladys through a comment she left on a piece I wrote last fall about freelancers and the gaps in ACA marketplace plans. Her comment was long, specific, and quietly devastating. She wasn’t asking for sympathy. She was correcting what she called an assumption in my reporting — that high-income freelancers have “options.” I reached out, and she agreed to talk. We met over video call on a Tuesday morning in March 2026, her home office visible behind her, a teenager’s backpack slung over a chair in the background.
A Solid Income That Suddenly Wasn’t Enough
Gladys Okonkwo, 40, has worked as a freelance graphic designer for eleven years. Based in Richmond, Virginia, she builds brand identities for mid-size companies and nonprofits. In 2024, she earned roughly $118,000 — a number she shared without hesitation, because, as she put it, the income is the point of the story.
“People hear ‘six figures’ and they think the hard part is over,” she told me. “They don’t see the insurance premiums, the quarterly taxes, the zero paid leave. I’m not complaining about my career. I’m saying the math people do in their heads about freelancers is wrong.”
Her husband works part-time while managing a chronic condition of his own. Their 17-year-old daughter is preparing to start college in the fall of 2026, and the family owns a modest home in Richmond’s Northside neighborhood that they purchased in 2019. On paper, they looked stable. Then January 2025 arrived.
When the Insurance Changed and the Prescriptions Tripled
Every year, Gladys re-enrolled in a marketplace health plan during open enrollment. She’d been on the same silver-tier plan for two years and had built a routine around it. When she re-enrolled in November 2024 for the 2025 plan year, she selected what appeared to be a comparable option. The premium was slightly lower — $689 per month versus $741 — and she took that as a good sign.
It wasn’t. The new plan had a different formulary, meaning the drugs on its covered list weren’t identical to her previous plan’s. Two of the three medications she takes regularly — one for a thyroid condition, one for anxiety — were classified as non-preferred brand drugs under the new plan’s tier structure. Her copay for those two drugs jumped from a combined $47 per month to $312 per month, effective January 1, 2025.
“I called the insurance company three times in January,” Gladys told me. “They kept saying the drugs were still covered. Which they were — just at a completely different cost share. There’s a difference between covered and affordable, and the plan documents don’t make that obvious when you’re comparing options.”
She tried requesting prior authorization for the preferred-tier version of one medication, a process that according to CMS guidance can take days to weeks and isn’t guaranteed to succeed. Her doctor submitted the paperwork in February 2025. It was denied in March.
The Rent Increase That Came at the Wrong Time
The Okonkwos own their home, but 2019’s purchase came with a variable-rate home equity line of credit they used for a renovation in 2022. That line’s monthly payment had climbed steadily with interest rates. More immediately, their property taxes were up for reassessment in 2025 — Richmond’s property values had risen sharply, and the Northside neighborhood where they live saw assessed values climb an average of 22% in the 2025 cycle.
Their annual property tax bill, which had been $4,100 in 2024, jumped to approximately $5,900 for 2025 — an increase of roughly $1,800. Gladys had not budgeted for it. She’d seen articles about rising assessments but, she admitted, had not pulled her own numbers until the bill arrived.
“I didn’t appeal,” she said plainly. “I didn’t know I could. Or I knew abstractly that you could, but I didn’t know the window was that short. By the time I was looking into it, it was already closed.”
She made partial payments through the summer of 2025 but fell behind by fall. As of our conversation in March 2026, she was still carrying approximately $1,400 in delinquent property tax, working through a payment arrangement with the City of Richmond’s finance department.
What ‘High Income’ Actually Covered — and What It Didn’t
It would be easy to look at Gladys’s $118,000 gross income and see a math problem that doesn’t add up. It does add up — but barely, and only if nothing goes wrong. As she walked me through her monthly picture, the margin became clear.
- Self-employment tax set-aside (approximately 25–30% quarterly): roughly $2,460 per month reserved
- Health insurance premium: $689 per month
- Mortgage and HELOC combined: $2,100 per month
- Daughter’s college prep expenses (test prep, application fees, campus visits): approximately $4,800 spread over 2025
- General household expenses for a family of three: roughly $3,200 per month
That leaves a cushion — but a thinner one than the gross income suggests. The prescription cost jump consumed most of it. “People look at my income and think I must have savings to fall back on,” Gladys told me. “I have some. But savings are not infinite, and I have a kid going to college in August.”
The Turning Point: Open Enrollment, Revisited
When November 2025 open enrollment arrived, Gladys approached it differently. She printed out her three prescriptions and used the formulary comparison tool available through HealthCare.gov to check each drug’s tier placement on every plan she was eligible for before looking at premiums. It took her about two hours.
She switched to a gold-tier plan with a higher monthly premium — $823 versus the $689 she’d been paying — but confirmed beforehand that her medications were classified as preferred generic or preferred brand under that plan’s formulary. Her estimated out-of-pocket cost for the same prescriptions dropped back to approximately $68 per month for 2026.
The higher-premium plan, once medications were factored in, actually costs her less annually. “That’s the thing nobody tells you,” she said. “A lower premium is not automatically the cheaper plan. I was so focused on the premium number that I didn’t look at what I’d actually be paying every month at the pharmacy.”
Where Things Stand Now
When I spoke with Gladys in late March 2026, she was cautiously steadier. The prescription situation was resolved for the current plan year. The property tax payment arrangement was on track — she owed two more installments of $700 each to clear the delinquency before the city would consider the account current. Her daughter had been accepted to Virginia Commonwealth University and was awaiting a financial aid package.
She was philosophical, though not resigned. Gladys is the kind of person who frames difficulty as information — she didn’t talk about 2025 as something that happened to her, but as something she now understood. Her biggest regret wasn’t the insurance switch itself. It was the hours she spent on the phone disputing decisions that, in hindsight, she didn’t have grounds to overturn.
“I kept thinking someone made a mistake,” she told me. “But no one made a mistake. That’s just how the system works. Once I understood that, I stopped fighting the system and started learning it.”
She mentioned, almost as an aside, that she’d also looked into Virginia’s property tax relief programs for the first time — and found that her household income disqualified her from most of them, which are means-tested toward lower-income homeowners. According to the Virginia Department of Taxation, many local relief programs are restricted to elderly or disabled residents, or those below certain income thresholds. Gladys fell outside those categories. She wasn’t bitter about it, but she noted it with the clarity of someone who had checked every door.
As our call wrapped up, her daughter wandered through the background, grabbed a jacket, and left without noticing she was on camera. Gladys watched her go with the specific kind of tired pride that parents carry when they’ve absorbed everything so someone else doesn’t have to. It was the most honest moment of the whole conversation, and she didn’t say a word about it.
She didn’t need to.
Leave a Reply