Most people assume that if you’re receiving Social Security disability benefits and still holding down a job, you’ve probably got things under control. That assumption, I’ve learned from reporting on benefits for several years, is one of the most quietly damaging myths in American financial life.
Tommy Dillard responded to a call-for-sources I posted on social media in early March 2026. I was looking for people actively navigating government benefits who felt the system wasn’t quite matching their reality. His message was brief: “I’m a math teacher. I can do the arithmetic. The arithmetic is the problem.” I called him the next morning.
A Diagnosis, a Decision, and a Benefit That Doesn’t Quite Cover It
When I sat down with Tommy Dillard over a video call from his home in St. Louis, the first thing I noticed was that he looked like someone who had rehearsed staying calm. He’s 40, teaches math at a public high school, and was diagnosed with relapsing-remitting multiple sclerosis in October 2022. By mid-2024, his symptoms — fatigue, vision disruption, coordination problems — forced him to reduce his classroom hours to part-time.
He was approved for Social Security Disability Insurance in the spring of 2024 after an initial denial and a successful appeal. His monthly SSDI benefit came in at $1,847. On top of that, he still teaches roughly 60 percent of a full schedule, which brings in approximately $1,380 per month in net wages — kept carefully under the SSA’s Substantial Gainful Activity threshold so his benefits remain intact.
His wife Rachel had been carrying a significant share of their household, earning roughly $72,000 annually as a marketing manager. Between the two of them, the family was managing — not comfortably, but managing. Tommy holds $94,000 in federal student loans from the master’s degree in mathematics education he completed in 2018. That debt runs him about $610 a month under an income-driven repayment plan.
“People hear ‘disability benefits’ and they think it means you’re taken care of,” Tommy told me. “But the benefit is calculated on your earnings history, not on what it actually costs to live with a chronic illness. Those are two very different numbers.”
January 2026: The Month the Budget Broke
Rachel Dillard was laid off from her job on January 9, 2026, when her employer conducted a company-wide reduction in force. The loss of her income was painful. The loss of her employer-sponsored health insurance was catastrophic.
The family had been paying $487 per month as their portion of Rachel’s employer health plan — a plan that covered Tommy’s MS medication, which carries a list price of over $6,800 per month without insurance. When that coverage ended, the Dillards had 60 days to find a replacement. They turned to COBRA continuation coverage.
The COBRA premium for their family plan came to $1,024 per month — more than double what they had been paying. In a single month, their fixed monthly expenses jumped by $537, with no corresponding increase in income.
Navigating the SSA While Everything Else Is on Fire
The financial pressure from January’s layoff wasn’t the only thing Tommy was managing. In November 2025, he had received a notice from the Social Security Administration informing him that his case had been selected for a Continuing Disability Review — a routine process the SSA uses to verify that recipients still meet the medical criteria for disability. For Tommy, the timing felt anything but routine.
The review dragged into early 2026. Tommy told me he spent three weekends in January gathering documentation: medical records from his neurologist, a statement from his school district confirming his reduced schedule, and letters from two treating physicians. He estimated he put in roughly 22 hours of unpaid administrative work into that process.
In February 2026, the SSA confirmed that Tommy’s disability status was unchanged and his benefits would continue uninterrupted. It was the small win he had mentioned in his initial message to me — and when he described receiving that letter, his voice shifted. “I actually sat in my car in the school parking lot and just breathed for a few minutes,” he told me. “I hadn’t realized how much I’d been holding.”
The Turning Point That Wasn’t Quite Enough
The CDR confirmation stabilized one piece of the picture, but the broader financial situation remained precarious. As Tommy explained it to me, winning the review felt like being told the house wasn’t on fire — while still owing three months of back-rent on it.
Rachel began collecting Missouri unemployment benefits in late January, which brought in approximately $480 per week — a meaningful cushion, but one with a clock on it. She has been actively job hunting since February. Tommy told me she had two second-round interviews as of late March 2026, though nothing had closed yet.
“I keep reminding myself that we’re not in crisis,” Tommy said. “But I also know the difference between not being in crisis and being okay. We’re in the space in between. And I don’t know how long we can stay there.”
The family has considered switching off COBRA and enrolling in an ACA marketplace plan, but Tommy’s MS medication creates a complicated calculus. He has a manufacturer’s patient assistance agreement that ties to his current formulary. Switching plans mid-year could disrupt that agreement and expose the family to medication costs that would overwhelm any premium savings.
What Tommy Wants Other Benefit Recipients to Know
Toward the end of our conversation, Tommy shifted from explaining his situation to reflecting on it. He said he had spoken to at least six colleagues over the past year who had no idea what SSDI actually paid, how the SGA limit worked, or what a Continuing Disability Review even was. “The information is out there,” he said, “but you have to know to go looking for it. Nobody hands you a roadmap.”
He mentioned that the SSA’s own website had been useful during his CDR — particularly the agency’s published guidance on continuing disability reviews and what documentation is typically required. He had also connected with a benefits counselor through his state’s vocational rehabilitation office, a resource he described as underused and underknown.
- SSDI benefits are based on your earnings history, not your current cost of living or medical expenses
- Working while on SSDI is permitted below the SGA threshold — in 2026, that limit is approximately $1,550 per month for non-blind recipients
- Continuing Disability Reviews are routine, but they require documentation and can create significant stress if you’re unprepared
- COBRA premiums can be more than double what employees paid under employer-sponsored plans
- State vocational rehabilitation programs offer free benefits counseling to SSDI recipients in most states
Tommy is not pessimistic, exactly. But he’s not comfortable either. He and Rachel have made a informal pact to reassess their finances in June — if Rachel hasn’t found employment by then, they’ll begin looking at whether relocating to a lower cost-of-living area is viable while Tommy continues teaching.
When I ended our call, Tommy was heading back to third-period algebra. He had a quiz to grade. The uncertainty of his financial situation would still be there when the bell rang, but he had a class of teenagers who needed to understand how to balance equations. He said that part, at least, he still felt good at.
What his story leaves me with — as a reporter who has covered benefits for years — is a clearer picture of the gap between what disability programs are designed to do and what people actually need them to do. For Tommy, that gap is $237 a month and widening. For many others navigating similar systems, it’s almost certainly larger.
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