The man in the tan work jacket was not trying to be overheard. He was standing two people behind me in line at a BP station on West Capitol Drive in Milwaukee on a Tuesday afternoon in late January, his phone pressed tight to his ear, speaking in a low, measured tone. “I just don’t know how long I can keep doing both,” he said. “The plan is expensive and Mama’s still asking for rent money.” I turned around without thinking, and he caught my eye. Something in his expression — not embarrassed, just tired — made me hand him my card when I reached him outside. He looked at it for a second, then said, “Yeah. Okay. Sure.”
That was how I met Nolan Dillard, 37, a custodian at a Milwaukee public elementary school. Two weeks later, I sat across from him at a diner on North Teutonia Avenue, and he laid out a financial picture that was more complicated than it looked from the outside.
A Good Income With a Quiet Leak
Nolan earns approximately $67,000 a year — a figure that includes base pay, consistent overtime shifts, and a small annual stipend for hazardous materials handling. By Wisconsin standards, and certainly by the standards of the custodial profession, that is a solid wage. He shares an apartment with a roommate, keeps his personal expenses lean, and has no dependents. On paper, he should be fine.
But for the past two years, Nolan had been sending roughly $700 a month back home to his family in Tuscaloosa, Alabama. His mother, 61, works part-time at a laundromat and has struggled with her own housing costs since his father passed in 2022. His younger brother, 29, has been in and out of work. The $700 — sometimes $650, sometimes $850 depending on the month — was not optional in Nolan’s mind. “That’s just what you do,” he told me flatly. “You don’t let your people fall.”
What the income figure does not show is what it costs to prop up two households from one paycheck. After rent, utilities, the family wire transfers, groceries, and his car payment, Nolan had been making a quiet calculation every month since early 2024: health insurance or everything else. He kept choosing everything else.
His job at the school district does offer a benefits package — but only to full-time employees classified under a specific union tier. Nolan’s role, though full-time in practice, had been classified under a contracted services arrangement for the past three years, which left him outside that coverage umbrella. He described trying to navigate the HR process to correct his classification as “like talking to a wall in a different language.”
Two Years Without Coverage — and One Close Call
Going uninsured at 37 felt manageable to Nolan until October 2024, when it didn’t. He woke up one morning with chest tightness and a shortness of breath he couldn’t shake for three days. He did not go to the emergency room. He waited it out, took some over-the-counter medication, and eventually felt better. He told almost no one.
He estimates that an ER visit without insurance for a cardiac evaluation could have cost him anywhere from $1,800 to over $6,000 out of pocket depending on the workup required. That math — the math of avoidance — is a calculation millions of uninsured Americans make quietly every year. According to Motley Fool’s cash reserves analysis, having even a modest emergency fund can be the difference between absorbing a health shock and going into debt — a reality Nolan understood viscerally but couldn’t yet act on.
The chest situation passed. But it shook something loose in him. “After that,” he said, “I started actually looking things up. I didn’t know what I was looking for. I just knew I couldn’t do that again.”
Finding the ACA Plan — and the Number That Surprised Him
In November 2024, during the standard ACA open enrollment window, Nolan finally sat down and went through HealthCare.gov for the first time. He expected the numbers to be unworkable. They weren’t — at least not entirely.
Based on his income and the premium tax credits available under the Affordable Care Act, Nolan qualified for a Silver-tier plan at approximately $194 per month after applying his tax credit subsidy. Before the credit, the same plan would have run him close to $480 a month. He stared at the screen for what he described as “a long time” before clicking enroll.
His coverage began January 1, 2025. The plan carries a $3,500 annual deductible, a detail Nolan noted with some wariness. But for the first time in two years, he had an insurance card in his wallet. “I took a picture of it,” he told me with a short laugh. “Which is dumb. But I did.”
The Larger Shadow: Social Security and What Comes Next
Nolan’s relief about health coverage was real and visible when we spoke. But underneath it was a tension he kept returning to — something longer and slower than a monthly premium. At 37, retirement feels abstract. But recent legislative developments had started to make it feel less so.
When I mentioned the recent reporting on Social Security’s funding trajectory, Nolan nodded immediately. He’d seen fragments of it on his phone. According to Motley Fool’s Social Security analysis, President Trump’s “big, beautiful bill” tax and spending law is projected to dig approximately a $169 billion hole in Social Security’s funding — constraining the program’s primary payroll tax income stream and potentially accelerating the timeline for benefit reductions.
For Nolan — who has no 401(k), no pension enrollment, and no investment accounts — Social Security is not a supplement. It is the plan. “I’ve been paying into it since I was nineteen,” he said. “That’s supposed to be there. That’s the deal.”
He understood the numbers imperfectly but felt them clearly. He is 37 years old. He has roughly 28 to 30 years until a conventional retirement age. A program he has counted on — quietly, without much thought — is now publicly described as underfunded and under new legislative pressure. That information settled on him the way inconvenient truths sometimes do: slowly, and then all at once.
Where Nolan Stands Today
When I spoke with Nolan in mid-February 2026, he had used his new health insurance once — a routine physical he’d put off for three years. The doctor found his blood pressure slightly elevated, prescribed a low-cost generic medication, and told him to come back in six months. “Ninety-dollar copay,” Nolan said. “Which stung. But it didn’t wreck me.” Before insurance, that visit could have cost him $200 to $300 out of pocket for the appointment alone, before any lab work.
He is still sending money home. The amount dropped slightly in February — $620 instead of $700 — because his brother picked up a warehouse shift. Nolan described that as a small mercy. He has started, tentatively, putting $80 a month into a savings account he opened at a credit union. It is not a retirement account. It is not invested anywhere. But it exists, which is more than it did in 2024.
The hopeful part of Nolan’s story is real. He found coverage. He used it. He started saving something. The scared part is equally real. He knows this is fragile — that one bad month, one family emergency in Alabama, one reclassification at work could undo the progress. “I’m not celebrating,” he said when I asked him how he felt about where things stood. “I’m just trying to not go backwards.”
I watched him walk back to his car after we finished talking — a man who earns more than many people his age, who props up people he loves, who spent two years choosing his family’s rent over his own health coverage, and who is now holding a small win carefully, the way you hold something you’ve dropped before. There was no clean resolution to offer him. Only the fact of where he stood, and the direction he was trying to walk.
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