Roughly 1 in 4 of today’s 20-year-olds will experience a disability before they reach retirement age, according to the Social Security Administration. Yet most of the public conversation around disability benefits focuses on older workers nearing retirement — not the 32-year-old math teacher sitting across from me at a folding table inside an Atlanta community center on a Tuesday afternoon in February 2026.
That teacher was Randall Castillo. The community center, which runs a financial literacy program in the Westview neighborhood, had referred his story to our publication after Randall attended one of their workshops and asked questions the facilitator said she had never heard before. She called them “too specific and too honest.” That description, I quickly learned, fits Randall exactly.
A Teacher With a Disability Check and a Spreadsheet Full of Gaps
Randall Castillo was diagnosed in early 2023 with a degenerative spinal condition that left him unable to stand for extended periods without significant pain. He applied for Social Security Disability Insurance in March of that year and, after an initial denial and a six-month appeals process, was approved in November 2023. His monthly SSDI benefit was set at $1,340 — a figure calculated from his earnings record as a relatively young worker who had not yet accumulated decades of high contributions.
By early 2024, Randall had returned to the classroom in a modified capacity, teaching two sections of Algebra II at a public high school in southwest Atlanta. His teaching income averages roughly $1,580 per month after taxes during the school year — a figure he watches closely because the SSA’s Substantial Gainful Activity threshold for 2026 sits at $1,620 per month for non-blind disabled workers. Exceed that ceiling and benefits can be suspended.
“I have a spreadsheet,” Randall told me, pulling out his phone to show me a color-coded Google Sheet. “Green means I’m under the SGA. Yellow means I need to slow down on substituting or tutoring. Red means I need to call the SSA before the month is over.” He laughed when he said it, but it was the kind of laugh that covers a lot of exhaustion.
When the Car Died, the Math Stopped Adding Up
In late October 2025, Randall’s 2014 Honda Civic threw a transmission fault code on his way to school. A mechanic in College Park gave him the diagnosis: $2,400 in repairs, minimum. Without the car, Randall cannot reliably get to work. Without work, his income drops to his SSDI check alone. And without the car, he also loses the ability to attend his biweekly physical therapy appointments, which are not optional — they are part of the treatment plan his physician documented in his disability file.
“I sat in that mechanic’s parking lot for about forty-five minutes,” Randall told me. “I was doing the math in my head, which is what I do for a living, and every answer I got was bad.”
This tension Randall described is not unique to him. The SSDI program’s Trial Work Period allows recipients to test their ability to work — in 2026, any month a recipient earns more than $1,110 counts as a trial work month. After nine trial work months within a rolling 60-month window, the SSA reviews whether the person is still eligible. Randall had already used five of those months by the time I met with him, something he tracked with the same precision he uses grading geometry proofs.
What Disability Benefits Actually Cover — and What They Don’t
When I asked Randall to walk me through his monthly budget, he did not hesitate. His rent in a shared apartment in East Point runs $820 per month. Utilities, groceries, and his phone add roughly $610. His Medicare Part B premium — SSDI recipients qualify for Medicare after a 24-month waiting period — comes to $185 per month in 2026. His out-of-pocket physical therapy copays average about $90 per month.
That is $1,705 in baseline monthly expenses before transportation, before emergencies, before the cost of being a person in the world. Against a $1,340 SSDI benefit, the deficit is immediate and structural.
- Monthly SSDI benefit: $1,340
- Rent: $820
- Utilities, groceries, phone: $610
- Medicare Part B premium: $185
- Physical therapy copays: $90
- Monthly shortfall (benefits alone): approximately $365
“People assume disability means you’re taken care of,” Randall told me. “Nobody told me the check would be smaller than my rent.” He paused, then added: “And that’s before anything breaks.”
The Small Win That Changed — and Did Not Change — Everything
In January 2026, Randall received a letter from the Social Security Administration he had been waiting on since August 2025. He had submitted a request for a reexamination of his initial benefit calculation, arguing that a six-month gap in his earnings record — caused by a period when his employer misreported his wages — had artificially reduced his Average Indexed Monthly Earnings (AIME), the number SSA uses to calculate SSDI amounts.
The SSA agreed. His benefit was recalculated and increased to $1,412 per month, retroactive to January 2025. He received a lump-sum back payment of $864 — twelve months at $72 more per month. It was, he told me, the most relief he had felt in two years.
He used $800 of the back payment toward the car repair. A family member covered the remaining $1,600 as an informal loan. The car is running. He is back at school. His monthly benefit — now $1,412 — still does not cover his fixed expenses without his teaching income, but the gap is narrower than it was in October when he sat in that mechanic’s parking lot.
What Comes Next — and What Still Worries Him
When I asked Randall what kept him up at night now that the immediate crisis had passed, his answer came quickly. He has four trial work months remaining before the SSA formally reviews whether his part-time teaching income disqualifies him from continuing to receive SSDI. He does not know what that review will conclude. And he does not have a plan for what happens if the benefit stops.
“I’m a math teacher,” he told me near the end of our conversation. “I understand probability. And right now the probability that this is all going to be fine feels lower than I want it to be.”
He is not wrong to be cautious. According to SSA’s annual statistical reports, the majority of SSDI recipients who return to work and exhaust their Trial Work Period face a benefits cessation review — a process that can take months and requires continued documentation of disability. For younger recipients like Randall who want to remain professionally active, the system offers a narrow corridor: productive enough to survive financially, restrained enough not to trigger a review.
Randall told me he plans to attend every community center financial workshop he can find between now and summer, when his teaching contract ends and his income drops. He is trying to build a three-month cash reserve — something he has never had before. His target is $4,200. As of our meeting in February, he had saved $640.
“It’s not nothing,” he said, looking at the number on his phone. “Before last year, it was zero. So right now, $640 is everything.”
I left the community center thinking about that spreadsheet — the green, yellow, and red cells that map the distance between a disability benefit and a functional life. Randall built that spreadsheet because no one handed him a guide when his condition changed his circumstances. He reverse-engineered the rules himself, the same way he teaches his students to work backward from an answer to find where the logic holds.
The system did not fail him completely. It corrected his benefit when pressed. But it also left him parsing federal income thresholds from a parking lot, in pain, with a broken car and a September rent payment on the horizon. The small win was real. The fear that it will not last is also real. Both of those things can be true at the same time — and for Randall Castillo, in April 2026, they are.
Sloane Avery Wren is a Senior Benefits Writer at Benefit Beat covering Social Security and government benefits programs. This article reflects reporting conducted in February 2026 and does not constitute financial or legal advice.
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